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Studies on enolization ofaldehydo-aldose derivatives

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
341
Issue
16
Identifiers
DOI: 10.1016/j.carres.2006.08.009
Keywords
  • Enol Acetates
  • Aldehydo-Sugars
  • Aldehydrol Diacetates
  • Photoisomerization
  • Aldehydrols
Disciplines
  • Chemistry

Abstract

Abstract Acetylation of the 2,3- O-isopropylidene derivative ( 1) of d-glyceraldehyde with hot acetic anhydride in the presence of sodium acetate give a mixture of ( Z)- and ( E)-enol acetates ( 2 and 3), together with the acetylated racemic aldehydrol ( 4) of 1. Likewise, the acyclic aldehydo 2,3:4,5-diisopropylidene acetals of d- and l-arabinose, d-xylose, and d-ribose underwent conversion into enol acetates, with the ( Z) isomers preponderating, and convertible photochemically into the corresponding ( E) isomers. Under other conditions of acetylation, the aldehydo derivatives were converted into the corresponding aldehydrol diacetates.

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