Glycosyl Alkoxythioimidates as Complementary Building Blocks for Chemical Glycosylation

It is reported that S-glycosyl O-methyl phenylcarbamothioates (SNea carbamothioates) have a fully orthogonal character in comparison to S-benzoxazolyl (SBox) glycosides. This complete orthogonality was revealed by performing competitive glycosylation experiments in the presence of various promoters....

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Bibliographic Details
Published inOrganic letters Vol. 12; no. 24; pp. 5628 - 5631
Main Authors Ranade, Sneha C, Kaeothip, Sophon, Demchenko, Alexei V
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.12.2010
Amer Chemical Soc
Subjects
Alcohols - chemistry
Chemistry
Chemistry, Organic
Glycosylation
Imidoesters - chemistry
Molecular Structure
Physical Sciences
Science & Technology
Sulfhydryl Compounds - chemistry
S-BENZOXAZOLYL GLYCOSIDES
THIOGLYCOSIDES
HIGHLY STEREOSPECIFIC METHOD
POTENT
VERSATILE
O-GLYCOSYLATION
OLIGOSACCHARIDE SYNTHESIS
DONORS
1,2-CIS-GLYCOSYLATION
PRINCIPLES
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Summary:It is reported that S-glycosyl O-methyl phenylcarbamothioates (SNea carbamothioates) have a fully orthogonal character in comparison to S-benzoxazolyl (SBox) glycosides. This complete orthogonality was revealed by performing competitive glycosylation experiments in the presence of various promoters. The results obtained indicate that SNea carbamothioates have a very similar reactivity profile to that of glycosyl thiocyanates, yet are significantly more stable and tolerate selected protecting group manipulations. These features make the SNea carbamothioates new promising building blocks for further utilization in oligosaccharide synthesis.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol1023079