From methyl d-glucopyranoside to methyl d-allopyranoside via the Mitsunobu reaction

Autor:	Aleksander Zamojski, Mikhail Kim, Barbara Grzeszczyk
Rok vydání:	1999
Předmět:	Methyl D-glucopyranoside Chemistry Reagent Yield (chemistry) Organic Chemistry Organic chemistry Mitsunobu reaction General Medicine Sugar Biochemistry Analytical Chemistry
Zdroj:	Carbohydrate Research. 320:244-249
ISSN:	0008-6215
DOI:	10.1016/s0008-6215(99)00160-3
Popis:	Methyl β-d-glucopyranoside reacted with a 4-molar excess of the Mitsunobu reagents (triphenylphosphine–diethyl azodicarboxylate–benzoic acid) under Weinges et al. [Carbohydr. Res., 164 (1987) 453–458] conditions to furnish four differently benzoylated methyl β-d-allopyranosides in a very good overall yield. The same reaction applied to methyl α-d-glucopyranoside yielded allosides in a low yield and nine other sugar products. These results give an insight into the course of the Mitsunobu esterification–inversion reaction.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::4b0ffd45bb16452a59ab4dd72442ba16 https://doi.org/10.1016/s0008-6215(99)00160-3 Zobrazit plný text záznamu Full Text from ScienceDirect