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Utilisation d'ylides du phosphore en chimie des sucres. XV. Synthèse de sucres à insaturation terminale
Author(s) -
Tronchet Jean M. J.,
Baehler Bruno,
Eder Hansjörg,
LeHong Nghiep,
Perret Françloise,
Poncet Joëlle,
Zumwald JeanBernard
Publication year - 1973
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19730560414
Subject(s) - chemistry , phosphonium , steric effects , medicinal chemistry , stereochemistry , organic chemistry
Treatment of 3‐O‐benzyl‐1, 2‐O‐isopropylidene‐3‐O‐methyl‐α‐ D ‐ xylo ‐pentodialdlo‐1,4‐furanose and 2,5‐anhydro‐3,4‐O‐isopropylidene‐ aldehydo ‐ D ‐ribose with moderately stable and stable phosphonium ylides led to the corresponding terminal‐unsaturated sugars obtained as a mixture of cis and trans isomers. The cis:trans ratios were determined by 1 H‐NMR. and (or) GLC. They showed that steric factors play an important role in the control of the stereochemistry of these reactions.