Journal
ORGANIC LETTERS
Volume 12, Issue 24, Pages 5628-5631Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol1023079
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Funding
- NIGMS [GM077170]
- NSF [CHE-0547566]
- AHA [0855743G]
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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
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