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Stereoselective synthesis of 4-C-methyl-2,3,5-tri-O-benzyl-d-ribofuranose and 4-C-methyl-2,3,5-tri-O-benzyl-l-lyxofuranose

✍ Scribed by Serge H Boyer; Bheemarao G Ugarkar; Mark D Erion

Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 231 KB
Volume: 44
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(03)00877-3

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✦ Synopsis

Sugar intermediates 4-C-methyl-2,3,5-tri-O-benzyl-D-ribofuranose (8b) and 4-C-methyl-2,3,5-tri-O-benzyl-L-lyxofuranose (8a) were synthesized by addition of alkylithium reagents to pentanones 3a,b. The nucleophilic additions proceeded with good stereoselectivity and good yields to give the titled compounds in four steps from perbenzylated methyl D-ribofuranoside and methyl 5%-deoxy-D-ribofuranoside.

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