A stereochemically general synthesis of methyl 2,4,6-trideoxy-4-methylthio-α-D-ribo-pyranoside, the thio sugar of esperamicin A1

Autor:	William R. Roush, Darin J. Gustin
Rok vydání:	1994
Předmět:	Esperamicin Stereochemistry Esperamicin A1 Organic Chemistry Thio Epoxide Biochemistry chemistry.chemical_compound Aniline Nucleophile chemistry Drug Discovery Stereoselectivity Aliphatic compound
Zdroj:	Tetrahedron Letters. 35:4931-4934
ISSN:	0040-4039
DOI:	10.1016/s0040-4039(00)73285-0
Popis:	A stereochemically general synthesis of methyl 2,4,6-trideoxy-4-methylthio-α-D-ribo-pyranoside ( 1b ), the thio sugar isolated from esperamicin, is described. The synthesis involves the neighboring group assisted delivery of a sulfur nucleophile to C(5) of epoxyalcohol 6 via aniline promoted cyclization of thioimidazolide 7 .
Databáze:	OpenAIRE
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