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Synlett 2001; 2001(8): 1217-1220
DOI: 10.1055/s-2001-16062
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Highly Efficient Synthesis of the Mannose Nonasaccharide of the N-Glycan Expressed on the HIV Glycoprotein gp 120

Yuliang Zhu* , Fanzuo Kong
  • *Research Center for Eco-Environmental Sciences, Academia Sinica, P.O. Box 2871, Beijing 100085, P.R. China; Fax 86-10-62 92 35 63; E-mail: fzkong@mail.rcees.ac.cn
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Publication Date:
31 December 2001 (online)

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A highly concise and effective synthesis of the mannose nonasaccharide of the glycan expressed on the HIV protein gp 120 was achieved via TMSOTf promoted selective 6-glycosylation of a tetrasaccharide 4,6-diol acceptor with a pentasaccharide donor followed by deprotection. The pentasaccharide was constructed by selective 3,6-diglycosylation of 1,2-O-ethylidene-β-d-mannopyranose with 2-O-acetyl-3,4,6-tri-O-benzoyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-O-benzoyl-α-d-mannopyranosyl trichloroimidate while the tetrasaccharide was obtained by selective 3-O-glycosylation of allyl 4,6-O-benzilidene-α-d-mannopyranoside with 2,3,4,6-tetra-O-benzoyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-tri-O-benzoyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-tri-O-benzoyl-α-d-mannopyranosyl trichloroimidate.

regio- and stereoselective synthesis - mannopyranosyl oligosaccharides