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

Autor:	Shun-Yuan Luo, Hung-Ju Tai, Yu-Hsuan Lih, Satpal Singh Badsara, Shih-An Yang, Hua-Shuan Lin, Chun-Hong Yeh, Ratnnadeep C. Sawant, Chung-Li Huang
Rok vydání:	2014
Předmět:	Sugar derivatives Ceramide chemistry.chemical_compound chemistry Stereochemistry General Chemical Engineering Wittig reaction Galactosyl ceramide Alcohol General Chemistry
Zdroj:	RSC Adv.. 4:26524-26534
ISSN:	2046-2069
DOI:	10.1039/c4ra03369h
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::991c1e3dbd755b37641bfd849e875d42 https://doi.org/10.1039/c4ra03369h Zobrazit plný text záznamu