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Literature DB >> 24502365

β-Selective mannosylation with a 4,6-silylene-tethered thiomannosyl donor.

Mads Heuckendorff¹, Jesper Bendix, Christian M Pedersen, Mikael Bols.

Abstract

Mannosylations using the new conformationally restricted donor phenyl 2,3-di-O-benzyl-4,6-O-(di-tert-butylsilylene)-1-thio-α-D-mannopyranoside (6) have been found to be β-selective with a variety of activation conditions. The simplest activation conditions were NIS/TfOH, in which case it is proposed that the β-mannoside is formed from β-selective glycosylation of the oxocarbenium ion 25 in a B(2,5) conformation.

Entities: Chemical Species

Year: 2014 PMID： 24502365 DOI： 10.1021/ol403722f

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

13 in total

1. Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by Bis-thiourea.

Authors: Qiuhan Li; Samuel M Levi; Eric N Jacobsen
Journal: J Am Chem Soc Date: 2020-06-26 Impact factor: 15.419

Review 2. The Experimental Evidence in Support of Glycosylation Mechanisms at the S_N1-S_N2 Interface.

Authors: Philip Ouma Adero; Harsha Amarasekara; Peng Wen; Luis Bohé; David Crich
Journal: Chem Rev Date: 2018-05-30 Impact factor: 60.622

3. Trifluoromethanesulfonate Anion as Nucleophile in Organic Chemistry.

Authors: Bibek Dhakal; Luis Bohé; David Crich
Journal: J Org Chem Date: 2017-09-05 Impact factor: 4.354

4. Automated fluorous-assisted solution-phase synthesis of β-1,2-, 1,3-, and 1,6-mannan oligomers.

Authors: Shu-Lun Tang; Nicola L B Pohl
Journal: Carbohydr Res Date: 2016-04-06 Impact factor: 2.104

5. Cation Clock Reactions for the Determination of Relative Reaction Kinetics in Glycosylation Reactions: Applications to Gluco- and Mannopyranosyl Sulfoxide and Trichloroacetimidate Type Donors.

Authors: Philip O Adero; Takayuki Furukawa; Min Huang; Debaraj Mukherjee; Pascal Retailleau; Luis Bohé; David Crich
Journal: J Am Chem Soc Date: 2015-08-07 Impact factor: 15.419

β-Selective mannosylation with a 4,6-silylene-tethered thiomannosyl donor.

1. Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by Bis-thiourea.

Review 2. The Experimental Evidence in Support of Glycosylation Mechanisms at the S_N1-S_N2 Interface.

3. Trifluoromethanesulfonate Anion as Nucleophile in Organic Chemistry.

4. Automated fluorous-assisted solution-phase synthesis of β-1,2-, 1,3-, and 1,6-mannan oligomers.

5. Cation Clock Reactions for the Determination of Relative Reaction Kinetics in Glycosylation Reactions: Applications to Gluco- and Mannopyranosyl Sulfoxide and Trichloroacetimidate Type Donors.

6. In situ preactivation strategies for the expeditious synthesis of oligosaccharides: A review.

7. Stereoselective β-Mannosylation via Anomeric O-Alkylation with L-Sugar-Derived Electrophiles.

Review 8. A propos of glycosyl cations and the mechanism of chemical glycosylation; the current state of the art.

9. A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides.

10. Automated Solution-Phase Synthesis of β-1,4-Mannuronate and β-1,4-Mannan.

Review 2. The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1-SN2 Interface.

Review 8. A propos of glycosyl cations and the mechanism of chemical glycosylation; the current state of the art.

Review 2. The Experimental Evidence in Support of Glycosylation Mechanisms at the S_N1-S_N2 Interface.