Header menu link for other important links
X
Stereoselective synthesis of a ketohexofuranose from an aldohexopyranose by a [6+1-1] strategy
Boga Sobhana Babu, Kalapattukuppuswamy Kuppuswamy B. Balasubramanian
Published in
2005
PMID: 15721349
Volume: 340
   
Issue: 4
Pages: 753 - 758
Abstract
Ozonolysis of 2-acetoxymethyl-1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-D- arabino-hex-1-enitol gave 1-O-acetyl-3,4,6-tri-O-benzyl-4-O-formyl-D-arabino- hex-2-ulose (5). Subsequent hydrolysis and acetylation of 5 provided 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-D-fructofuranose 6 in excellent yield. This methodology allows specific deuteration at C-1 of a protected D-fructofuranose derivative. This approach therefore could serve as [6+1-1] formulation for hexose series inter-conversion, that is, aldohexopyranose to ketohexofuranose. © 2005 Elsevier Ltd. All rights reserved.
About the journal
JournalCarbohydrate Research
ISSN00086215
Open AccessNo
Concepts (24)
  •  related image
    ACETYLATION
  •  related image
    Complexation
  •  related image
    Derivatives
  •  related image
    Hydrolysis
  •  related image
    Synthesis (chemical)
  •  related image
    Ozonolysis
  •  related image
    Stereoselective synthesis
  •  related image
    Stereochemistry
  •  related image
    ALDOHEXOPYRANOSE
  •  related image
    Furan derivative
  •  related image
    KETOHEXOFURANOSE
  •  related image
    Pyran derivative
  •  related image
    Unclassified drug
  •  related image
    Article
  •  related image
    Methodology
  •  related image
    Priority journal
  •  related image
    Synthesis
  •  related image
    Arabinose
  •  related image
    Carbohydrate conformation
  •  related image
    Deuterium
  •  related image
    HEXOSES
  •  related image
    KETOSES
  •  related image
    Molecular structure
  •  related image
    Ozone