Superarming the S-Benzoxazolyl Glycosyl Donors by Simple 2-O-Benzoyl-3,4,6-tri-O-benzyl Protection

Mydock, Laurel K.; Demchenko, Alexei V.

doi:10.1021/ol800345j

Cited by 83 publications

(71 citation statements)

References 57 publications

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“…The concept of "armed-disarmed" glycosyl donors was proposed by Fraser-Reid and co-workers (22). The "superdisarmed" donor is less reactive than the typical "disarmed" donor, which has 2,3,4,6-tetra-O-benzoyl protecting groups, because the 3,4,6-O-tribenzoyl work as electron-withdrawing groups and the 2-O-benzyl group does not work as a neighboring group (23). Turnbull and co-workers have already reported sulfonium ions of furanosides by the direct method using MeOTf (24).…”

Section: B Preparation Of Glycosyl Sulfonium Ionsmentioning

confidence: 99%

Sulfonium Ions as Reactive Glycosylation Intermediates

Nokami

2012

TIGG

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Glycosyl sulfonium ions are positively charged organosulfur compounds having the positive charge on a sulfur atom that is covalently attached to the anomeric carbon. These species have received attention because of their potential as glycosylation intermediates. Recently, novel methods for the preparation of glycosyl sulfonium ions have been reported. The reactivity of glycosyl sulfonium ions can be controlled by changing the substituents on the sulfur atom and the protecting groups of the hydroxyl groups. Recent studies have also shown that glycosyl sulfonium ions are unique glycosylation intermediates that have modifiable reactivity.

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Section: B Preparation Of Glycosyl Sulfonium Ionsmentioning

confidence: 99%

Sulfonium Ions as Reactive Glycosylation Intermediates

Nokami

2012

TIGG

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“…The superarming in glycosyl donors of this series is based on the combination of electronic and anchimeric effects rationalized by the existence of the O2/O5 cooperative effect in glycosylation. 36–38 Glycosidation of the SBiz-H donor 12 resulted in another interesting outcome: both DMTST and MeI were effective, and the corresponding disaccharide 14 was obtained in high yields in 8 and 15 h, respectively (entries 9 and 10). Again, complete β -stereo-selectivity observed in this reaction shall be attributed to the participation of the 2- O -benzoyl group.…”

Section: Resultsmentioning

confidence: 99%

S-Benzimidazolyl (SBiz) Imidates as a Platform for Oligosaccharide Synthesis via Active–Latent, Armed–Disarmed, Selective, and Orthogonal Activations

et al. 2017

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This article describes the development of S-benzimidazolyl (SBiz) imidates as versatile building blocks for oligosaccharide synthesis. The SBiz imidates have been originally developed as a new platform for active-latent glycosylations. This article expands upon the utility of these compounds. The application to practically all common concepts for the expeditious oligosaccharide synthesis including selective, chemoselective, and orthogonal strategies is demonstrated. The strategy development was made possible thanks to our enhanced understanding of the reaction mechanism and the modes by which SBiz imidates interact with various promoters of glycosylation.

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“…With the discovery of multiple reactivity levels ranging from the superdisarmed to the superarmed building blocks and systems [68,[121][122][123][124], the versatility of the chemoselective approach to oligosaccharide synthesis was enhanced. Wong and co-workers devised a mathematical approach, assigning relative reactivity values (RRVs) to a wide library of building blocks that were then used for oligosaccharide assembly in one-pot [125].…”

Section: Automation Of the One-pot Oligosaccharide Synthesis In Solutionmentioning

confidence: 99%