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Literature DB >> 12713313

Ph2SO/Tf2O: a powerful promotor system in chemoselective glycosylations using thioglycosides.

Jeroen D C Codée¹, Remy E J N Litjens, René den Heeten, Herman S Overkleeft, Jacques H van Boom, Gijs A van der Marel.

Abstract

Diphenylsulfoxide in combination with triflic anhydride provides a very potent thiophilic glycosylation promotor system, capable of activating disarmed thioglycosides. The usefulness of this novel thiophilic activator is illustrated in a successful chemoselective glycosylation sequence in which the donor thioglycoside in the first condensation step may be either armed or disarmed. [reaction: see text]

Entities: Chemical Species

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Year: 2003 PMID： 12713313 DOI： 10.1021/ol034312t

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

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Cited

40 in total

1. On the nitrile effect in L-rhamnopyranosylation.

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Journal: Carbohydr Res Date: 2006-04-27 Impact factor: 2.104

2. Stereoselectivity of Conformationally Restricted Glucosazide Donors.

Authors: Stefan van der Vorm; Herman S Overkleeft; Gijsbert A van der Marel; Jeroen D C Codée
Journal: J Org Chem Date: 2017-04-25 Impact factor: 4.354

3. 4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene] acetals. improved second-generation acetals for the stereoselective formation of beta-D-mannopyranosides and regioselective reductive radical fragmentation to beta-D-rhamnopyranosides. scope and limitations.

Authors: David Crich; Albert A Bowers
Journal: J Org Chem Date: 2006-04-28 Impact factor: 4.354

4. Convergent synthesis of a beta-(1-->3)-mannohexaose.

Authors: David Crich; Baolin Wu; Prasanna Jayalath
Journal: J Org Chem Date: 2007-08-01 Impact factor: 4.354

5. Superarming the S-benzoxazolyl glycosyl donors by simple 2-O-benzoyl-3,4,6-tri-O-benzyl protection.

Authors: Laurel K Mydock; Alexei V Demchenko
Journal: Org Lett Date: 2008-05-01 Impact factor: 6.005

6. Stereocontrolled synthesis of the D- and L-glycero-beta-D-manno-heptopyranosides and their 6-deoxy analogues. Synthesis of methyl alpha-l-rhamno-pyranosyl-(1-->3)-D-glycero-beta-D-manno-heptopyranosyl- (1-->3)-6-deoxy-glycero-beta-D-manno-heptopyranosyl-(1-->4)-alpha-L- rhamno-pyranoside, a tetrasaccharide subunit of the lipopolysaccharide from Plesimonas shigelloides.

Authors: David Crich; Abhisek Banerjee
Journal: J Am Chem Soc Date: 2006-06-21 Impact factor: 15.419

Ph2SO/Tf2O: a powerful promotor system in chemoselective glycosylations using thioglycosides.

1. On the nitrile effect in L-rhamnopyranosylation.

2. Stereoselectivity of Conformationally Restricted Glucosazide Donors.

3. 4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene] acetals. improved second-generation acetals for the stereoselective formation of beta-D-mannopyranosides and regioselective reductive radical fragmentation to beta-D-rhamnopyranosides. scope and limitations.

4. Convergent synthesis of a beta-(1-->3)-mannohexaose.

5. Superarming the S-benzoxazolyl glycosyl donors by simple 2-O-benzoyl-3,4,6-tri-O-benzyl protection.

Review 7. Expeditious oligosaccharide synthesis via selective, semi-orthogonal, and orthogonal activation.

8. Methodology development and physical organic chemistry: a powerful combination for the advancement of glycochemistry.

9. Synthesis of the antigenic tetrasaccharide side chain from the major glycoprotein of Bacillus anthracis exosporium.

10. Cowpea mosaic virus capsid: a promising carrier for the development of carbohydrate based antitumor vaccines.