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Literature DB >> 16494484

Efficient glycosidation of a phenyl thiosialoside donor with diphenyl sulfoxide and triflic anhydride in dichloromethane.

Abstract

The formation of sialic acid glycosides with a thiosialic acid derivative, diphenyl sulfoxide, and trifluoromethanesulfonic anhydride is reported. With an excess of diphenyl sulfoxide, glycal formation can be completely suppressed and excellent yields are obtained for coupling to a wide range of primary, secondary, and tertiary acceptors.

Entities: Chemical Species

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Year: 2006 PMID： 16494484 PMCID： PMC2615465 DOI： 10.1021/ol060030s

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

12 in total

1. Chemoselective Iterative Dehydrative Glycosylation This research was supported by the National Institutes of Health (Grant no.: GM-58833), the Arnold and Mabel Beckman Foundation (BYI), Glaxo Wellcome Inc., and the Alfred P. Sloan Foundation. D.Y.G. is a Cottrell Scholar of Research Corporation.

Authors: Hien M. Nguyen; Jennifer L. Poole; David Y. Gin
Journal: Angew Chem Int Ed Engl Date: 2001-01-19 Impact factor: 15.336

2. Recent advances in o-sialylation.

Authors: G J Boons; A V Demchenko
Journal: Chem Rev Date: 2000-12-13 Impact factor: 60.622

3. Interhalogens (ICl/IBr) and AgOTf in thioglycoside activation; synthesis of bislactam analogues of ganglioside GD3.

Authors: Andréas Meijer; Ulf Ellervik
Journal: J Org Chem Date: 2004-09-17 Impact factor: 4.354

4. Stereoselective alpha-Sialylation with Sialyl Xanthate and Phenylsulfenyl Triflate as a Promotor.

Authors: Valeri Martichonok; George M. Whitesides
Journal: J Org Chem Date: 1996-03-08 Impact factor: 4.354

5. 1-Benzenesulfinyl piperidine/trifluoromethanesulfonic anhydride: a potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages.

Authors: D Crich; M Smith
Journal: J Am Chem Soc Date: 2001-09-19 Impact factor: 15.419

6. 2-O-propargyl ethers: readily cleavable, minimally intrusive protecting groups for beta-mannosyl donors.

Authors: David Crich; Prasanna Jayalath
Journal: Org Lett Date: 2005-05-26 Impact factor: 6.005

7. A stereoselective approach for the synthesis of alpha-sialosides.

Authors: C D Meo; A V Demchenko; G J Boons
Journal: J Org Chem Date: 2001-08-10 Impact factor: 4.354

8. One-pot synthesis of sialo-containing glycosyl amino acids by use of an N-trichloroethoxycarbonyl-beta-thiophenyl sialoside.

Authors: Hiroshi Tanaka; Masaatsu Adachi; Takashi Takahashi
Journal: Chemistry Date: 2005-01-21 Impact factor: 5.236

9. Dehydrative sialylation with C2-hemiketal sialyl donors.

Authors: Jannine M Haberman; David Y Gin
Journal: Org Lett Date: 2003-07-10 Impact factor: 6.005

10. High-resolution 1H-NMR spectroscopy of free and glycosidically linked O-acetylated sialic acids.

Authors: J Haverkamp; H van Halbeek; L Dorland; J F Vliegenthart; R Pfeil; R Schauer
Journal: Eur J Biochem Date: 1982-02

15 in total

1. Influence of the O3 protecting group on stereoselectivity in the preparation of C-mannopyranosides with 4,6-O-benzylidene protected donors.

Authors: David Crich; Indrajeet Sharma
Journal: J Org Chem Date: 2010-11-11 Impact factor: 4.354

2. Stereoselective synthesis of alpha-keto-deoxy-D-glycero-D-galacto-nonulosonic acid glycosides by means of the 4,5-O-carbonate protecting group.

Authors: David Crich; Chandrasekhar Navuluri
Journal: Angew Chem Int Ed Engl Date: 2010-04-12 Impact factor: 15.336

Review 3. 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

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

Authors: David Crich
Journal: J Org Chem Date: 2011-10-04 Impact factor: 4.354

5. Dissecting the influence of oxazolidinones and cyclic carbonates in sialic acid chemistry.

Authors: Pavan K Kancharla; Chandrasekhar Navuluri; David Crich
Journal: Angew Chem Int Ed Engl Date: 2012-09-13 Impact factor: 15.336

6. O-sialylation with N-acetyl-5-n,4-o-carbonyl-protected thiosialoside donors in dichloromethane: facile and selective cleavage of the oxazolidinone ring.

Authors: David Crich; Wenju Li
Journal: J Org Chem Date: 2007-03-06 Impact factor: 4.354

7. Synthesis and Stereocontrolled Equatorially Selective Glycosylation Reactions of a Pseudaminic Acid Donor: Importance of the Side-Chain Conformation and Regioselective Reduction of Azide Protecting Groups.

Authors: Bibek Dhakal; David Crich
Journal: J Am Chem Soc Date: 2018-10-25 Impact factor: 15.419

8. Pre-activation-based one-pot synthesis of an alpha-(2,3)-sialylated core-fucosylated complex type bi-antennary N-glycan dodecasaccharide.

Authors: Bin Sun; Balasubramanian Srinivasan; Xuefei Huang
Journal: Chemistry Date: 2008 Impact factor: 5.236

9. A stable, commercially available sulfenyl chloride for the activation of thioglycosides in conjunction with silver trifluoromethanesulfonate.

Authors: David Crich; Feng Cai; Fan Yang
Journal: Carbohydr Res Date: 2008-03-10 Impact factor: 2.104

10. A Highly Efficient Glycosidation of Glycosyl Chlorides by Using Cooperative Silver(I) Oxide-Triflic Acid Catalysis.

Authors: Scott A Geringer; Yashapal Singh; Daniel J Hoard; Alexei V Demchenko
Journal: Chemistry Date: 2020-06-02 Impact factor: 5.236

Review 3. The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1-SN2 Interface.

Review 3. The Experimental Evidence in Support of Glycosylation Mechanisms at the S_N1-S_N2 Interface.