An improved synthesis of 5-thio-d-ribose from d-ribono-1,4-lactone

Autor:	Imane Stasik, Daniel Beaupère, Gilles Demailly, Jérôme Lalot
Rok vydání:	2002
Předmět:	chemistry.chemical_classification Molecular Structure Stereochemistry Chemistry Ribose Organic Chemistry General Medicine Biochemistry Analytical Chemistry Lactones chemistry.chemical_compound Yield (chemistry) 5-thio-D-ribose Lactone
Zdroj:	Carbohydrate Research. 337:1411-1416
ISSN:	0008-6215
Popis:	5-Thio-D-ribopyranose was synthesized from D-ribono-1,4-lactone (1) by two approaches: (i) 5-bromo-5-deoxy-D-ribono-1,4-lactone (2) was successively transformed into 5-bromo-5-deoxy, 5-S-acetyl-5-thio or 5-thiocyanato-D-ribofuranose derivatives; appropriate treatment then lead to 5-thio-D-ribopyranose (7) in 46-48% overall yield and; (ii) 2 was transformed into the 5-S-acetyl-5-thio-D-ribono-1,4-lactone derivative (11). Reduction and deprotection of 11 afforded 5-thio-D-ribopyranose (7) in 57% overall yield.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::ee2cc0c8618e00b2ef9d561346566ca0 https://doi.org/10.1016/s0008-6215(02)00170-2 Zobrazit plný text záznamu Full Text from ScienceDirect