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Literature DB >> 19856360

Phenylthiomethyl glycosides: convenient synthons for the formation of azidomethyl and glycosylmethyl glycosides and their derivatives.

David Crich¹, Fan Yang.

Abstract

Entities: Chemical Species

Mesh：

Substances：

Year: 2009 PMID： 19856360 PMCID： PMC3064763 DOI： 10.1002/anie.200904168

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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28 in total

1. Selectinminus signCarbohydrate Interactions: From Natural Ligands to Designed Mimics.

Authors: Eric E. Simanek; Glenn J. McGarvey; Jill A. Jablonowski; Chi-Huey Wong
Journal: Chem Rev Date: 1998-04-02 Impact factor: 60.622

2. A strategy for the synthesis of sulfated peptides.

Authors: Travis Young; Laura L Kiessling
Journal: Angew Chem Int Ed Engl Date: 2002-09-16 Impact factor: 15.336

3. S,X-acetals in nucleoside chemistry. III. Synthesis of 2'- and 3'-O-azidomethyl derivatives of ribonucleosides.

Authors: S G Zavgorodny; A E Pechenov; V I Shvets; A I Miroshnikov
Journal: Nucleosides Nucleotides Nucleic Acids Date: 2000 Oct-Dec Impact factor: 1.381

4. On the preparation of carbohydrate-protein conjugates using the traceless Staudinger ligation.

Authors: Cyrille Grandjean; Alain Boutonnier; Catherine Guerreiro; Jean-Michel Fournier; Laurence A Mulard
Journal: J Org Chem Date: 2005-09-02 Impact factor: 4.354

5. Ruthenium-catalyzed azide-alkyne cycloaddition: scope and mechanism.

Authors: Brant C Boren; Sridhar Narayan; Lars K Rasmussen; Li Zhang; Haitao Zhao; Zhenyang Lin; Guochen Jia; Valery V Fokin
Journal: J Am Chem Soc Date: 2008-06-21 Impact factor: 15.419

6. Triazole: the keystone in glycosylated molecular architectures constructed by a click reaction.

Authors: Alessandro Dondoni
Journal: Chem Asian J Date: 2007-06-04

7. Glycosylthiomethyl chloride: a new species for S-neoglycoconjugate synthesis. Synthesis of 1-N-glycosylthiomethyl-1,2,3-triazoles.

Authors: Xiangming Zhu; Richard R Schmidt
Journal: J Org Chem Date: 2004-02-20 Impact factor: 4.354

8. The reaction of thio acids with azides: a new mechanism and new synthetic applications.

Authors: Ning Shangguan; Sreenivas Katukojvala; Rachel Greenberg; Lawrence J Williams
Journal: J Am Chem Soc Date: 2003-07-02 Impact factor: 15.419

9. Stereoselective synthesis of (1-alkoxyalkyl) alpha- and beta-D-glucopyranosiduronates (acetal-glucopyranosiduronates): a new approach to specific cytostatics for the treatment of cancer.

Authors: L F Tietze; R Seele; B Leiting; T Krach
Journal: Carbohydr Res Date: 1988-09-15 Impact factor: 2.104

Review 10. Recent applications of the Cu(I)-catalysed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in carbohydrate chemistry.

Authors: Simone Dedola; Sergey A Nepogodiev; Robert A Field
Journal: Org Biomol Chem Date: 2007-03-05 Impact factor: 3.876

6 in total

Review 1. 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

2. Stereoselective C-glycoside formation with 2-O-benzyl-4,6-O-benzylidene protected 3-deoxy gluco- and mannopyranoside donors: comparison with O-glycoside formation.

Authors: Myriame Moumé-Pymbock; David Crich
Journal: J Org Chem Date: 2012-10-11 Impact factor: 4.354

3. En Route to the Transformation of Glycoscience: A Chemist's Perspective on Internal and External Crossroads in Glycochemistry.

Authors: David Crich
Journal: J Am Chem Soc Date: 2020-12-22 Impact factor: 15.419

Phenylthiomethyl glycosides: convenient synthons for the formation of azidomethyl and glycosylmethyl glycosides and their derivatives.

1. Selectinminus signCarbohydrate Interactions: From Natural Ligands to Designed Mimics.

2. A strategy for the synthesis of sulfated peptides.

3. S,X-acetals in nucleoside chemistry. III. Synthesis of 2'- and 3'-O-azidomethyl derivatives of ribonucleosides.

4. On the preparation of carbohydrate-protein conjugates using the traceless Staudinger ligation.

5. Ruthenium-catalyzed azide-alkyne cycloaddition: scope and mechanism.

6. Triazole: the keystone in glycosylated molecular architectures constructed by a click reaction.

7. Glycosylthiomethyl chloride: a new species for S-neoglycoconjugate synthesis. Synthesis of 1-N-glycosylthiomethyl-1,2,3-triazoles.

8. The reaction of thio acids with azides: a new mechanism and new synthetic applications.

9. Stereoselective synthesis of (1-alkoxyalkyl) alpha- and beta-D-glucopyranosiduronates (acetal-glucopyranosiduronates): a new approach to specific cytostatics for the treatment of cancer.

Review 10. Recent applications of the Cu(I)-catalysed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in carbohydrate chemistry.

Review 1. The Experimental Evidence in Support of Glycosylation Mechanisms at the S_N1-S_N2 Interface.

2. Stereoselective C-glycoside formation with 2-O-benzyl-4,6-O-benzylidene protected 3-deoxy gluco- and mannopyranoside donors: comparison with O-glycoside formation.

3. En Route to the Transformation of Glycoscience: A Chemist's Perspective on Internal and External Crossroads in Glycochemistry.

4. Long-Range Stereodirecting Participation across a Glycosidic Linkage in Glycosylation Reactions.

5. Total synthesis of periploside A, a unique pregnane hexasaccharide with potent immunosuppressive effects.

6. Chloromethyl Glycosides as Versatile Synthons to Prepare Glycosyloxymethyl-Prodrugs.

Review 10. Recent applications of the Cu(I)-catalysed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in carbohydrate chemistry.

Review 1. The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1-SN2 Interface.

Review 1. The Experimental Evidence in Support of Glycosylation Mechanisms at the S_N1-S_N2 Interface.