A one-pot synthetic method for the hetero-bifunctionalization of α-cyclodextrin at the secondary hydroxyl side with high clockwise-counterclockwise selectivity

α-Cyclodextrin and 3,3′-benzophenonedisulfonylimidazole in a unimolecular ratio were stirred at 40 °C for 1 h in the presence of a catalytic amount of Cs 2 CO 3 in DMF, and then treated with sodium hydroxide to give 2 A ,3 A -mannoepoxy-2 B -sulfonyl-α-cyclodextrin in 14% isolated yield. The isomer...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2017-05, Vol.15 (19), p.477-48
Main Authors: Huang, Xi, Yasunaga, Shun, Fukudome, Makoto, Chen, Wen-Hua, Yuan, De-Qi
Format: Article
Language:English
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Summary:α-Cyclodextrin and 3,3′-benzophenonedisulfonylimidazole in a unimolecular ratio were stirred at 40 °C for 1 h in the presence of a catalytic amount of Cs 2 CO 3 in DMF, and then treated with sodium hydroxide to give 2 A ,3 A -mannoepoxy-2 B -sulfonyl-α-cyclodextrin in 14% isolated yield. The isomer with the reversed saccharide sequence was not detected. The first one-pot synthetic method has been established to ensure the sequence-selective, highly efficient introduction of two different functionalities into the secondary side of α-cyclodextrin.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob00719a