Tetrahedron letters

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

HI Duynstee, MC de Koning, GA van der Marel…

Index: Duynstee, Howard I.; De Koning, Martijn C.; Van Der Marel, Gijs A.; Van Boom, Jacques H. Tetrahedron Letters, 1998 , vol. 39, # 23 p. 4129 - 4132

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Citation Number: 5

Abstract

Chemoselective NIS/cat. TfOH-mediated glycosylation of ethyl 2, 3, 4-tri-O-benzoyl-1-thio-β- d-glucopyranoside (4) with ethyl 2, 3-di-O-acetyl-5-O-benzyl-1-thio-α/β-d-erythro- apiofuranoside (3) gave dimer 5 in an excellent yield. BF3Et2O-catalysed condensation of the α-trichloroacetimidate 18, accessible in two steps from 5, with 3, 4, 5-trimethoxyphenol gave β-linked derivative 19 which could be transformed in five steps into the title ...