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Literature DB >> 18763796

Direct and stereoselective synthesis of alpha-linked 2-deoxyglycosides.

Jin Park¹, Thomas J Boltje, Geert-Jan Boons.

Abstract

alpha-Linked 2-deoxyglycosides were conveniently obtained by employing a glycosyl donor having a participating ( S)-(phenylthiomethyl)benzyl moiety at C-6, whereas 2,6-dideoxy-alpha-glycosides could be prepared by BF 3.Et 2O-promoted activation of allyl glycosyl donors.

Entities: Chemical Gene Species

Mesh：

Substances：
Glycosides

Year: 2008 PMID： 18763796 PMCID： PMC2631667 DOI： 10.1021/ol801833n

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

28 in total

1. One-pot synthesis of 2-deoxy-beta-oligosaccharides.

Authors: R Pongdee; B Wu; G A Sulikowski
Journal: Org Lett Date: 2001-11-01 Impact factor: 6.005

2. Synthesis of complex carbohydrates and glycoconjugates: enzyme-based and programmable one-pot strategies.

Authors: K M Koeller; C H Wong
Journal: Chem Rev Date: 2000-12-13 Impact factor: 60.622

3. Synthesis of 4-O-alpha-L-fucopyranosyl-L-fucose and methyl 4-O-beta-L-fucopyranosyl-alpha-L-fucopyranoside.

Authors: M Dejter-Juszynski; H M Flowers
Journal: Carbohydr Res Date: 1975-05 Impact factor: 2.104

4. Stereoselective glycosylation reactions with chiral auxiliaries.

Authors: Jin-Hwan Kim; Hai Yang; Geert-Jan Boons
Journal: Angew Chem Int Ed Engl Date: 2005-01-28 Impact factor: 15.336

5. Diversifying vancomycin via chemoenzymatic strategies.

Authors: Xun Fu; Christoph Albermann; Changsheng Zhang; Jon S Thorson
Journal: Org Lett Date: 2005-04-14 Impact factor: 6.005

6. Direct and stereoselective synthesis of beta-linked 2,6-deoxyoligosaccharides.

Authors: Hiroshi Tanaka; Atsushi Yoshizawa; Takashi Takahashi
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

7. Syntheses and biological activities of rebeccamycin analogues with uncommon sugars.

Authors: Guisheng Zhang; Jie Shen; Hao Cheng; Lizhi Zhu; Lanyan Fang; Sanzhong Luo; Mark T Muller; Gun Eui Lee; Lijun Wei; Yuguo Du; Duxin Sun; Peng George Wang
Journal: J Med Chem Date: 2005-04-07 Impact factor: 7.446

8. De novo approach to 2-deoxy-beta-glycosides: asymmetric syntheses of digoxose and digitoxin.

Authors: Maoquan Zhou; George A O'Doherty
Journal: J Org Chem Date: 2007-03-06 Impact factor: 4.354

Review 9. 'Sweetening' natural products via glycorandomization.

Authors: Byron R Griffith; Joseph M Langenhan; Jon S Thorson
Journal: Curr Opin Biotechnol Date: 2005-10-13 Impact factor: 9.740

10. Efficient route to 2-deoxy beta-O-aryl-d-glycosides via direct displacement of glycosyl iodides.

Authors: Son N Lam; Jacquelyn Gervay-Hague
Journal: Org Lett Date: 2003-10-30 Impact factor: 6.005

10 in total

Review 1. Methods for 2-Deoxyglycoside Synthesis.

Authors: Clay S Bennett; M Carmen Galan
Journal: Chem Rev Date: 2018-06-28 Impact factor: 60.622

2. Recent Advances in Transition Metal-Catalyzed Glycosylation.

Authors: Matthew J McKay; Hien M Nguyen
Journal: ACS Catal Date: 2012-06-14 Impact factor: 13.084

3. Stereoselective assembly of complex oligosaccharides using anomeric sulfonium ions as glycosyl donors.

Authors: Tao Fang; Kai-For Mo; Geert-Jan Boons
Journal: J Am Chem Soc Date: 2012-04-18 Impact factor: 15.419

4. Assembly of a Complex Branched Oligosaccharide by Combining Fluorous-Supported Synthesis and Stereoselective Glycosylations using Anomeric Sulfonium Ions.

Authors: Wei Huang; Qi Gao; Geert-Jan Boons
Journal: Chemistry Date: 2015-08-06 Impact factor: 5.236