Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 72, Issue 18, Pages 6947-6955Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo071191s
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Funding
- NIGMS NIH HHS [R15 GM077170, R15 GM077170-01, GM077170] Funding Source: Medline
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As a part of a program for developing new versatile building blocks for stereoselective glycosylation and convergent oligosaccharide synthesis, we demonstrated that S-benzoxazolyl (SBox) glycosides are stable toward major protecting group manipulations employed in carbohydrate chemistry. On the other hand, they can be glycosidated under relatively mild reaction conditions to afford either 1,2-trans or 1,2-cis-linked disaccharides. Selective and chemoselective activations of the SBox moiety were also proved to be feasible, which was demonstrated by synthesizing a number of oligosaccharide sequences.
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