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Synthesis of 3,4,5-trimethoxyphenyl 5″-O-caffeoyl-β-d-erythro-apiofuranosyl-(1→6)-β-d-glucopyranoside: Kelampayoside B

✍ Scribed by Howard I. Duynstee; Martijn C. de Koning; Gijs A. van der Marel; Jacques H. van Boom

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
235 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

Chemoselective NIS/cat. TfOH-mediated glycosylation of ethyl 2,3,4-tri-O-benzoyl-l-thio-[3-D-glucopyranoside (4) with ethyl 2,3-di-O-acetyl-5-O-benzyl-l-thio-fflfi-D-erythro-apiofuranoside (3) gave dimer 5 in an excellent yield. BF3"Et20-catalysed condensation of the ct-trichloroacetimidate 18, accessible in two steps from 5, with 3,4,5-trimethoxypbenol gave [~-linked derivative 19 which could be transformed in five steps into the title compound.

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