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Literature DB >> 22864908

Facile TMSOTf-catalyzed preparation of 2-deoxy α-O-aryl-D-glycosides from glycosyl acetates.

Guofang Yang¹, Qingbing Wang, Xiaosheng Luo, Jianbo Zhang, Jie Tang.

Abstract

2-Deoxy α-O-aryl glycosides were conveniently obtained by reaction of 2-deoxy-glycosyl acetates with phenols in the presence of TMSOTf as the promoter. The current method provides the O-aryl glycosides with good to excellent yields, and sole alpha selectivity.

Entities: Chemical

Mesh：

Substances：

Year: 2012 PMID： 22864908 DOI： 10.1007/s10719-012-9429-7

Source DB: PubMed Journal: Glycoconj J ISSN： 0282-0080 Impact factor: 2.916

18 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. Dual stereoselectivity of 1-(2'-carboxy)benzyl 2-deoxyglycosides as glycosyl donors in the direct construction of 2-deoxyglycosyl linkages.

Authors: Kwan Soo Kim; Jin Park; Yong Joo Lee; Yong Sung Seo
Journal: Angew Chem Int Ed Engl Date: 2003-01-27 Impact factor: 15.336

3. 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

Review 4. The role of carbohydrates in biologically active natural products.

Authors: A C Weymouth-Wilson
Journal: Nat Prod Rep Date: 1997-04 Impact factor: 13.423

5. 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 6. Aromatic O-glycosylation.

Authors: Mårten Jacobsson; Jesper Malmberg; Ulf Ellervik
Journal: Carbohydr Res Date: 2006-05-02 Impact factor: 2.104

7. Concise synthesis of a pentasaccharide related to the anti-leishmanial triterpenoid saponin isolated from Maesa balansae.

Authors: Vishal Kumar Rajput; Balaram Mukhopadhyay
Journal: J Org Chem Date: 2008-08-02 Impact factor: 4.354

2. Stereoselective organocatalyzed glycosylations - thiouracil, thioureas and monothiophthalimide act as Brønsted acid catalysts at low loadings.

Authors: G A Bradshaw; A C Colgan; N P Allen; I Pongener; M B Boland; Y Ortin; E M McGarrigle
Journal: Chem Sci Date: 2018-10-22 Impact factor: 9.825

2 in total

Facile TMSOTf-catalyzed preparation of 2-deoxy α-O-aryl-D-glycosides from glycosyl acetates.

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

2. Dual stereoselectivity of 1-(2'-carboxy)benzyl 2-deoxyglycosides as glycosyl donors in the direct construction of 2-deoxyglycosyl linkages.

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

Review 4. The role of carbohydrates in biologically active natural products.

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

Review 6. Aromatic O-glycosylation.

7. Concise synthesis of a pentasaccharide related to the anti-leishmanial triterpenoid saponin isolated from Maesa balansae.

Review 8. Recent advances in the synthesis of 2-deoxy-glycosides.

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

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

1. TMSOTf mediated stereoselective synthesis of α-C-glycosides from unactivated aryl acetylenes.

2. Stereoselective organocatalyzed glycosylations - thiouracil, thioureas and monothiophthalimide act as Brønsted acid catalysts at low loadings.