An Efficient Synthesis of Valienamine via Ring-Closing Metathesis

An efficient synthesis of valienamine is described. Valienamine was synthesized starting from commercially available 2,3,4,6-tetra-O-benzyl-d-glucose in nine steps, using ring-closing metathesis of (4S,5S,6S)-4,5,6-tribenzyloxy-7-(benzyloxymethyl)octa-1,7-dien-3-ol as a key step.

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Bibliographic Details
Published in:Journal of organic chemistry 2005-04, Vol.70 (8), p.3299-3302
Main Authors: Chang, Young-Kil, Lee, Bo-Young, Kim, Dong Jun, Lee, Gwan Sun, Jeon, Heung Bae, Kim, Kwan Soo
Format: Article
Language:English
Subjects:
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemistry
Cyclization
Cyclohexenes
Exact sciences and technology
Hexosamines - analysis
Hexosamines - chemical synthesis
Magnetic Resonance Spectroscopy
Molecular Structure
Organic chemistry
Preparations and properties
Stereoisomerism
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Description
Summary:An efficient synthesis of valienamine is described. Valienamine was synthesized starting from commercially available 2,3,4,6-tetra-O-benzyl-d-glucose in nine steps, using ring-closing metathesis of (4S,5S,6S)-4,5,6-tribenzyloxy-7-(benzyloxymethyl)octa-1,7-dien-3-ol as a key step.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo047735x