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A highly stereoselective and practical synthesis of cyclomannohexaose, Cyclo{→4)-[α-d-Manp-(1→4)-]5-α-d-Manp-(1→}, amannoisomer of cyclomaltohexaose

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
192
Identifiers
DOI: 10.1016/0008-6215(89)85173-0

Abstract

Abstract Phenylselenyl triflate-promoted cycloglycosylation of methyl O-(2,3,6-tri- O-benzyl-α- d-mannopyranosyl)-(1→4) - [ O-(2,3,6-tri- O-benzyl-α- d-mannopyranosyl)-(1→4)] 4-2,3,6-tri- O-benzyl-1-thio-α- d-mannopyranoside afforded 64% of cyclo{→4)-[ O-(2,3,6-tri- O-benzyl-α- d-mannopyranosyl)-(1→4)] 5- O-(2,3,6-tri- O-benzyl-α- d-mannopyranosyl)-(1→} which was then hydrogenolysed to give a manno isomer of cyclomaltohexaose (α-cyclodextrin). The key mannohexaosyl intermediate for cycloglycosylation was prepared in a stereocontrolled manner from 3,6-di- O-benzyl-4- O-chloroacetyl-2- O- p-methylbenzoyl-α- d-mannopyranosyl trichloroacetimidate and p-methoxyphenyl 3,6-di- O-benzyl-2- O- p-methylbenzoyl-α- d-mannopyranoside.

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