Abstract
[reaction: see text] D-Ribonolactone (6) was transformed into N-((fluorenylmethoxy)carbonyl)-3,4-bis-O-(tert-butyldimethylsilyl)-D-2,3-cis-3,4-cis-3,4-dihydroxyproline (13) in nine chemical steps. This represents a potentially general strategy for the synthesis of 3,4-dihydroxyprolines, utilizing the pentose sugar series as starting materials.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aluminum Compounds
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Animals
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Aza Compounds / chemistry
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Hydroxyproline / chemical synthesis*
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Indicators and Reagents
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Lithium Compounds
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Magnetic Resonance Spectroscopy
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Pentoses / chemistry*
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Stereoisomerism
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Structure-Activity Relationship
Substances
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3,4-dihydroxyproline
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Aluminum Compounds
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Aza Compounds
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Indicators and Reagents
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Lithium Compounds
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Pentoses
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lithium aluminum hydride
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Hydroxyproline