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A versatile and new highly stereoselective approach to the synthesis of l-glycero-d-manno-heptopyranosides

✍ Scribed by G.J.P.H Boons; G.A van der Marel; J.H van Boom

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 226 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)95167-0

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✦ Synopsis

The reaction of (phenyldimethyl)silylmethyl.magnesiu chloride with benzyl 2,3,4tri-0-benzyl-a-D-manno-hexodialdo-1,5-pyranoside affords the corresponding L-glycero-Dmanno-addition product having at C-7 the phenyldim:thylsilyl (PDMSi) group. The latter silanyl compound survived benzylation as veil as glpc>sylation at OH-6, and the PDMSi group could be unmasked with overall retention of configuration Lo give a free hydroxyl.

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