Synthesis of Tetra-O-acetyl-1-thio-α-D-glucopyranose by Reaction of Tetra-O-acetyl-α-D-glucopyranosyl Bromide with N,N-Dimethylthioformamide

Autor:	Toshio Takido, Manabu Seno, Takayoshi Fujihira, Haruo Kamijo, Gen Arakawa
Rok vydání:	2003
Předmět:	Anomer biology Thio General Medicine biology.organism_classification Medicinal chemistry D-Glucopyranose Adduct chemistry.chemical_compound Column chromatography chemistry Bromide Yield (chemistry) Tetra
Zdroj:	ChemInform. 34
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200333198
Popis:	A reaction system was found to prepare tetra‐O‐acetyl‐1‐thio‐d‐glycopyranose in both α and β‐forms. Methanolysis of the adduct prepared from the reaction of tetra‐O‐acetyl‐α‐d‐glucopyranosyl bromide with N,N‐dimethylthioformamide afforded the corresponding tetra‐O‐acetyl‐1‐thio‐d‐glucopyranose with an anomer ratio α/β of 52:48 in 98% yield. The anomer mixture was easily separated by column chromatography to obtain the product of α‐form. This synthetic method is very convenient to proceed by one‐pot reaction under ordinary conditions.
Databáze:	OpenAIRE
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