Synthesis of C-Linked Glycopyranosyl Serines via a Chiral Glycine Enolate Equivalent

The stereoselective preparation of C-linked d-gluco- and d-galactopyranosyl l-serines in their α and β forms is herein reported. The syntheses require the conversion of the allyl C-glycopyranosides into their iodoethyl derivatives, which then undergo substitution with the Williams' chiral glyci...

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Bibliographic Details
Published inOrganic letters Vol. 4; no. 22; pp. 3963 - 3965
Main Authors Nolen, Ernest G, Watts, Micah M, Fowler, Daniel J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 31.10.2002
Amer Chemical Soc
Subjects
Alkylation
Chemistry
Chemistry, Organic
Galactosides - chemistry
Glucosides - chemistry
Glycine - analogs & derivatives
Glycine - chemistry
Glycoconjugates - chemical synthesis
Glycopeptides - chemical synthesis
Monosaccharides - chemical synthesis
Physical Sciences
Science & Technology
Serine - chemical synthesis
AMINO-ACID SYNTHESIS
ANALOG
METHYLENE ISOSTERES
ALPHA-GALACTOSERINE
GLYCOSYL SERINE
ASYMMETRIC SYNTHESES
GALACTOPYRANOSYL-L-SERINE
GLYCOPEPTIDES
STEREOSELECTIVE SYNTHESIS
GLYCOBIOLOGY
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Summary:The stereoselective preparation of C-linked d-gluco- and d-galactopyranosyl l-serines in their α and β forms is herein reported. The syntheses require the conversion of the allyl C-glycopyranosides into their iodoethyl derivatives, which then undergo substitution with the Williams' chiral glycine enolate equivalent. Deprotection and acetylation affords Boc-protected amino acids for peptide synthesis.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol026839w