Microwave-Assisted One-Pot Synthesis of 1,6-Anhydrosugars and Orthogonally Protected Thioglycosides

Living organisms employ glycans as recognition elements because of their large structural information density. Well-defined sugar structures are needed to fully understand and take advantage of glycan functions, but sufficient quantities of these compounds cannot be readily obtained from natural sou...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2014-10, Vol.136 (41), p.14425-14431
Main Authors: Ko, Yen-Chun, Tsai, Cheng-Fang, Wang, Cheng-Chung, Dhurandhare, Vijay M, Hu, Pu-Ling, Su, Ting-Yang, Lico, Larry S, Zulueta, Medel Manuel L, Hung, Shang-Cheng
Format: Article
Language:English
Subjects:
Carbohydrate Conformation
Microwaves
Oligosaccharides - chemical synthesis
Oligosaccharides - chemistry
Thioglycosides - chemical synthesis
Thioglycosides - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a381t-f2ab9b39c29479d5cf02e1fad623fa209f874bd674a1556cf142fb24d4fd93fd3
cites cdi_FETCH-LOGICAL-a381t-f2ab9b39c29479d5cf02e1fad623fa209f874bd674a1556cf142fb24d4fd93fd3
container_end_page 14431
container_issue 41
container_start_page 14425
container_title Journal of the American Chemical Society
container_volume 136
creator Ko, Yen-Chun
Tsai, Cheng-Fang
Wang, Cheng-Chung
Dhurandhare, Vijay M
Hu, Pu-Ling
Su, Ting-Yang
Lico, Larry S
Zulueta, Medel Manuel L
Hung, Shang-Cheng
description Living organisms employ glycans as recognition elements because of their large structural information density. Well-defined sugar structures are needed to fully understand and take advantage of glycan functions, but sufficient quantities of these compounds cannot be readily obtained from natural sources and have to be synthesized. Among the bottlenecks in the chemical synthesis of complex glycans is the preparation of suitably protected monosaccharide building blocks. Thus, easy, rapid, and efficient methods for building-block acquisition are desirable. Herein, we describe routes directly starting from the free sugars toward notable monosaccharide derivatives through microwave-assisted one-pot synthesis. The procedure followed the in situ generation of per-O-trimethylsilylated monosaccharide intermediates, which provided 1,6-anhydrosugars or thioglycosides upon treatment with either trimethylsilyl trifluoromethanesulfonate or trimethyl­(4-methylphenylthio)­silane and ZnI2, respectively, under microwave irradiation. We successfully extended the methodology to regioselective protecting group installation and manipulation toward a number of thioglucosides and the glycosylation of persilylated derivatives, all of which were conducted in a single vessel. These developed approaches open the possibility for generating arrays of suitably protected building blocks for oligosaccharide assembly in a short period with minimal number of purification stages.
doi_str_mv 10.1021/ja504804v
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1639495621</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1639495621</sourcerecordid><originalsourceid>FETCH-LOGICAL-a381t-f2ab9b39c29479d5cf02e1fad623fa209f874bd674a1556cf142fb24d4fd93fd3</originalsourceid><addsrcrecordid>eNptkE1Lw0AQQBdRbK0e_AOSi6BgdHezm2SPpfgFlRas57DZjyYlzdadpJJ_b0prT56GGR4P5iF0TfAjwZQ8rSTHLMVse4KGhFMcckLjUzTEGNMwSeNogC4AVv3KaErO0YByKgjDdIjUR6m8-5FbE44BSmiMDma1CeeuCT67uilMfwycDchDHI7rotPeQbuUHgJZ96hvCrd0tayqLph71xi1MyyK0i2rTjkotYFLdGZlBebqMEfo6-V5MXkLp7PX98l4GsooJU1oqcxFHglFBUuE5spiaoiVOqaRlRQLmyYs13HCJOE8VpYwanPKNLNaRFZHI3S39268-24NNNm6BGWqStbGtZCROBJM8JiSHr3fo_3zAN7YbOPLtfRdRnC2a5odm_bszUHb5mujj-RfxB643QNSQbZyre9zwD-iX8f2fpc</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1639495621</pqid></control><display><type>article</type><title>Microwave-Assisted One-Pot Synthesis of 1,6-Anhydrosugars and Orthogonally Protected Thioglycosides</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Ko, Yen-Chun ; Tsai, Cheng-Fang ; Wang, Cheng-Chung ; Dhurandhare, Vijay M ; Hu, Pu-Ling ; Su, Ting-Yang ; Lico, Larry S ; Zulueta, Medel Manuel L ; Hung, Shang-Cheng</creator><creatorcontrib>Ko, Yen-Chun ; Tsai, Cheng-Fang ; Wang, Cheng-Chung ; Dhurandhare, Vijay M ; Hu, Pu-Ling ; Su, Ting-Yang ; Lico, Larry S ; Zulueta, Medel Manuel L ; Hung, Shang-Cheng</creatorcontrib><description>Living organisms employ glycans as recognition elements because of their large structural information density. Well-defined sugar structures are needed to fully understand and take advantage of glycan functions, but sufficient quantities of these compounds cannot be readily obtained from natural sources and have to be synthesized. Among the bottlenecks in the chemical synthesis of complex glycans is the preparation of suitably protected monosaccharide building blocks. Thus, easy, rapid, and efficient methods for building-block acquisition are desirable. Herein, we describe routes directly starting from the free sugars toward notable monosaccharide derivatives through microwave-assisted one-pot synthesis. The procedure followed the in situ generation of per-O-trimethylsilylated monosaccharide intermediates, which provided 1,6-anhydrosugars or thioglycosides upon treatment with either trimethylsilyl trifluoromethanesulfonate or trimethyl­(4-methylphenylthio)­silane and ZnI2, respectively, under microwave irradiation. We successfully extended the methodology to regioselective protecting group installation and manipulation toward a number of thioglucosides and the glycosylation of persilylated derivatives, all of which were conducted in a single vessel. These developed approaches open the possibility for generating arrays of suitably protected building blocks for oligosaccharide assembly in a short period with minimal number of purification stages.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja504804v</identifier><identifier>PMID: 25291402</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Carbohydrate Conformation ; Microwaves ; Oligosaccharides - chemical synthesis ; Oligosaccharides - chemistry ; Thioglycosides - chemical synthesis ; Thioglycosides - chemistry</subject><ispartof>Journal of the American Chemical Society, 2014-10, Vol.136 (41), p.14425-14431</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a381t-f2ab9b39c29479d5cf02e1fad623fa209f874bd674a1556cf142fb24d4fd93fd3</citedby><cites>FETCH-LOGICAL-a381t-f2ab9b39c29479d5cf02e1fad623fa209f874bd674a1556cf142fb24d4fd93fd3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,786,790,27957,27958</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25291402$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ko, Yen-Chun</creatorcontrib><creatorcontrib>Tsai, Cheng-Fang</creatorcontrib><creatorcontrib>Wang, Cheng-Chung</creatorcontrib><creatorcontrib>Dhurandhare, Vijay M</creatorcontrib><creatorcontrib>Hu, Pu-Ling</creatorcontrib><creatorcontrib>Su, Ting-Yang</creatorcontrib><creatorcontrib>Lico, Larry S</creatorcontrib><creatorcontrib>Zulueta, Medel Manuel L</creatorcontrib><creatorcontrib>Hung, Shang-Cheng</creatorcontrib><title>Microwave-Assisted One-Pot Synthesis of 1,6-Anhydrosugars and Orthogonally Protected Thioglycosides</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>Living organisms employ glycans as recognition elements because of their large structural information density. Well-defined sugar structures are needed to fully understand and take advantage of glycan functions, but sufficient quantities of these compounds cannot be readily obtained from natural sources and have to be synthesized. Among the bottlenecks in the chemical synthesis of complex glycans is the preparation of suitably protected monosaccharide building blocks. Thus, easy, rapid, and efficient methods for building-block acquisition are desirable. Herein, we describe routes directly starting from the free sugars toward notable monosaccharide derivatives through microwave-assisted one-pot synthesis. The procedure followed the in situ generation of per-O-trimethylsilylated monosaccharide intermediates, which provided 1,6-anhydrosugars or thioglycosides upon treatment with either trimethylsilyl trifluoromethanesulfonate or trimethyl­(4-methylphenylthio)­silane and ZnI2, respectively, under microwave irradiation. We successfully extended the methodology to regioselective protecting group installation and manipulation toward a number of thioglucosides and the glycosylation of persilylated derivatives, all of which were conducted in a single vessel. These developed approaches open the possibility for generating arrays of suitably protected building blocks for oligosaccharide assembly in a short period with minimal number of purification stages.</description><subject>Carbohydrate Conformation</subject><subject>Microwaves</subject><subject>Oligosaccharides - chemical synthesis</subject><subject>Oligosaccharides - chemistry</subject><subject>Thioglycosides - chemical synthesis</subject><subject>Thioglycosides - chemistry</subject><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNptkE1Lw0AQQBdRbK0e_AOSi6BgdHezm2SPpfgFlRas57DZjyYlzdadpJJ_b0prT56GGR4P5iF0TfAjwZQ8rSTHLMVse4KGhFMcckLjUzTEGNMwSeNogC4AVv3KaErO0YByKgjDdIjUR6m8-5FbE44BSmiMDma1CeeuCT67uilMfwycDchDHI7rotPeQbuUHgJZ96hvCrd0tayqLph71xi1MyyK0i2rTjkotYFLdGZlBebqMEfo6-V5MXkLp7PX98l4GsooJU1oqcxFHglFBUuE5spiaoiVOqaRlRQLmyYs13HCJOE8VpYwanPKNLNaRFZHI3S39268-24NNNm6BGWqStbGtZCROBJM8JiSHr3fo_3zAN7YbOPLtfRdRnC2a5odm_bszUHb5mujj-RfxB643QNSQbZyre9zwD-iX8f2fpc</recordid><startdate>20141015</startdate><enddate>20141015</enddate><creator>Ko, Yen-Chun</creator><creator>Tsai, Cheng-Fang</creator><creator>Wang, Cheng-Chung</creator><creator>Dhurandhare, Vijay M</creator><creator>Hu, Pu-Ling</creator><creator>Su, Ting-Yang</creator><creator>Lico, Larry S</creator><creator>Zulueta, Medel Manuel L</creator><creator>Hung, Shang-Cheng</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20141015</creationdate><title>Microwave-Assisted One-Pot Synthesis of 1,6-Anhydrosugars and Orthogonally Protected Thioglycosides</title><author>Ko, Yen-Chun ; Tsai, Cheng-Fang ; Wang, Cheng-Chung ; Dhurandhare, Vijay M ; Hu, Pu-Ling ; Su, Ting-Yang ; Lico, Larry S ; Zulueta, Medel Manuel L ; Hung, Shang-Cheng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-f2ab9b39c29479d5cf02e1fad623fa209f874bd674a1556cf142fb24d4fd93fd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Carbohydrate Conformation</topic><topic>Microwaves</topic><topic>Oligosaccharides - chemical synthesis</topic><topic>Oligosaccharides - chemistry</topic><topic>Thioglycosides - chemical synthesis</topic><topic>Thioglycosides - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ko, Yen-Chun</creatorcontrib><creatorcontrib>Tsai, Cheng-Fang</creatorcontrib><creatorcontrib>Wang, Cheng-Chung</creatorcontrib><creatorcontrib>Dhurandhare, Vijay M</creatorcontrib><creatorcontrib>Hu, Pu-Ling</creatorcontrib><creatorcontrib>Su, Ting-Yang</creatorcontrib><creatorcontrib>Lico, Larry S</creatorcontrib><creatorcontrib>Zulueta, Medel Manuel L</creatorcontrib><creatorcontrib>Hung, Shang-Cheng</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ko, Yen-Chun</au><au>Tsai, Cheng-Fang</au><au>Wang, Cheng-Chung</au><au>Dhurandhare, Vijay M</au><au>Hu, Pu-Ling</au><au>Su, Ting-Yang</au><au>Lico, Larry S</au><au>Zulueta, Medel Manuel L</au><au>Hung, Shang-Cheng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Microwave-Assisted One-Pot Synthesis of 1,6-Anhydrosugars and Orthogonally Protected Thioglycosides</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2014-10-15</date><risdate>2014</risdate><volume>136</volume><issue>41</issue><spage>14425</spage><epage>14431</epage><pages>14425-14431</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><notes>ObjectType-Article-1</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-2</notes><notes>content type line 23</notes><abstract>Living organisms employ glycans as recognition elements because of their large structural information density. Well-defined sugar structures are needed to fully understand and take advantage of glycan functions, but sufficient quantities of these compounds cannot be readily obtained from natural sources and have to be synthesized. Among the bottlenecks in the chemical synthesis of complex glycans is the preparation of suitably protected monosaccharide building blocks. Thus, easy, rapid, and efficient methods for building-block acquisition are desirable. Herein, we describe routes directly starting from the free sugars toward notable monosaccharide derivatives through microwave-assisted one-pot synthesis. The procedure followed the in situ generation of per-O-trimethylsilylated monosaccharide intermediates, which provided 1,6-anhydrosugars or thioglycosides upon treatment with either trimethylsilyl trifluoromethanesulfonate or trimethyl­(4-methylphenylthio)­silane and ZnI2, respectively, under microwave irradiation. We successfully extended the methodology to regioselective protecting group installation and manipulation toward a number of thioglucosides and the glycosylation of persilylated derivatives, all of which were conducted in a single vessel. These developed approaches open the possibility for generating arrays of suitably protected building blocks for oligosaccharide assembly in a short period with minimal number of purification stages.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25291402</pmid><doi>10.1021/ja504804v</doi><tpages>7</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0002-7863
ispartof Journal of the American Chemical Society, 2014-10, Vol.136 (41), p.14425-14431
issn 0002-7863
1520-5126
language eng
recordid cdi_proquest_miscellaneous_1639495621
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects Carbohydrate Conformation
Microwaves
Oligosaccharides - chemical synthesis
Oligosaccharides - chemistry
Thioglycosides - chemical synthesis
Thioglycosides - chemistry
title Microwave-Assisted One-Pot Synthesis of 1,6-Anhydrosugars and Orthogonally Protected Thioglycosides
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-09-22T16%3A27%3A28IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Microwave-Assisted%20One-Pot%20Synthesis%20of%201,6-Anhydrosugars%20and%20Orthogonally%20Protected%20Thioglycosides&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Ko,%20Yen-Chun&rft.date=2014-10-15&rft.volume=136&rft.issue=41&rft.spage=14425&rft.epage=14431&rft.pages=14425-14431&rft.issn=0002-7863&rft.eissn=1520-5126&rft_id=info:doi/10.1021/ja504804v&rft_dat=%3Cproquest_cross%3E1639495621%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a381t-f2ab9b39c29479d5cf02e1fad623fa209f874bd674a1556cf142fb24d4fd93fd3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1639495621&rft_id=info:pmid/25291402&rfr_iscdi=true