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An unusual Wittig reaction with sugar derivatives: exclusive formation of a 4-deoxy analogue of α-galactosyl ceramide

Author:
Sawant, Ratnnadeep C., Lih, Yu-Hsuan, Yang, Shih-An, Yeh, Chun-Hong, Tai, Hung-Ju, Huang, Chung-Li, Lin, Hua-Shuan, Badsara, Satpal Singh, Luo, Shun-Yuan
Source:
RSC advances 2014 v.4 no.50 pp. 26524-26534
ISSN:
2046-2069
Subject:
alcohols, ceramides, chemical reactions, reducing sugars
Abstract:
The Wittig reaction of the pyrano-type reducing sugars undergoes an unexpected formation of dienes through the elimination of a benzyloxy group in the presence of t-BuOK. LiHMDS is used rather than t-BuOK to prevent alcohol elimination in the same sugar derivatives. Collectively, t-BuOK has unusual functions in the Wittig reaction that correspond with other bases such as LiHMDS, NaH, and n-BuLi. This unusual function of t-BuOK showed that a unique 4-deoxy-5-hydroxyl analogue 2 of α-galactosyl ceramide was formed exclusively.
Agid:
6650473