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Synthesis of some 2-C-alkyl-2,3-dideoxy-alpha,beta-L-glycero-tetrurono-1,4-lactones . Evaluation as antitumor agents.

Authors
  • Blazis, V J
  • Hawkins, E S
  • Baker, D C
Type
Published Article
Journal
Carbohydrate Research
Publisher
Elsevier
Publication Date
Feb 03, 1994
Volume
253
Pages
225–233
Identifiers
PMID: 8156549
Source
Medline
License
Unknown

Abstract

A series of 3-C-alkyl-2,3-dideoxy-5-O-trityl-D-erythro-pentono-1,4-lactones were detritylated. The resultant free-hydroxy compounds were converted to their respective 2-C-alkyl-2,3-dideoxy-alpha,beta-L-glycero-tetrurono-1,4-lactones (L-sugar numbering) in a one-vessel reaction sequence of (a) conversion of the lactones to their aldonic acid sodium salts, (b) cleavage of the resulting aldonates with sodium metaperiodate, and (c) acidification, followed by acetylation, to give the title compounds. The unsubstituted tetrurono-1,4-lactones were inhibitory toward L1210 leukemia cells at concentrations in the 10(-4) M range.

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