Affordable Access

deepdyve-link
Publisher Website

A convenient synthesis of short-chain α-(1 → 2) mannopyranosyl oligosaccharides.

Authors
  • Zhang, Wenhui1
  • Wang, Jun2
  • Serianni, Anthony S3
  • Pan, Qingfeng4
  • 1 Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN, 46556-5670, USA.
  • 2 Omicron Biochemicals, Inc., 115 South Hill Street, South Bend, IN, 46617-2701, USA.
  • 3 Omicron Biochemicals, Inc., 115 South Hill Street, South Bend, IN, 46617-2701, USA; Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN, 46556-5670, USA.
  • 4 Omicron Biochemicals, Inc., 115 South Hill Street, South Bend, IN, 46617-2701, USA. Electronic address: [email protected]
Type
Published Article
Journal
Carbohydrate research
Publication Date
Mar 01, 2020
Volume
489
Pages
107897–107897
Identifiers
DOI: 10.1016/j.carres.2019.107897
PMID: 32092558
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

Sugar 1,2-orthoesters are by-products of chemical glycosylation reactions that can be subsequently rearranged in situ to give trans glycosides. They have been used as donors in the synthesis of the latter glycosides with good regio- and stereo-selectivity. Alkyl α-(1 → 2) linked mannopyranosyl disaccharides have been reported as the major products from the rearrangement of mannopyranosyl orthoesters. Recent studies in this laboratory have shown that α-(1 → 2) linked mannopyranosyl di-, tri- and tetrasaccharides can be obtained in one step from mannopyranosyl allyl orthoester under optimized reaction conditions. In addition to the expected mono- and disaccharides (56%), allyl 2,3,4,6-tetra-O-acetyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-tri-O-acetyl-α-d-mannopyranosyl-(1 → 2)-tri-O-acetyl-α-d-mannopyranoside and allyl 2,3,4,6-tetra-O-acetyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-tri-O-acetyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-tri-O-acetyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-tri-O-acetyl-α-d-mannopyranoside were obtained in 23% and 6% isolated yields, respectively, from the oligomerization of a β-d-mannopyranosyl allyl 1,2-orthoester, along with small amounts of higher DP oligomers. Possible mechanisms for the oligomerization and side reactions are proposed based on NMR and mass spectrometric data. Copyright © 2019 Elsevier Ltd. All rights reserved.

Report this publication

Statistics

Seen <100 times