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Literature DB >> 21892457

Reverse orthogonal strategy for oligosaccharide synthesis.

Kohki Fujikawa¹, N Vijaya Ganesh, Yih Horng Tan, Keith J Stine, Alexei V Demchenko.

Abstract

Herein, we report the invention of a novel expeditious concept for oligosaccharide synthesis. Unlike the classic orthogonal strategy based on leaving groups, the reverse approach is based on orthogonal protecting groups, herein p-methoxybenzyl and 4-pentenoyl, which allows for efficient oligosaccharide assembly in the reverse direction. This journal is © The Royal Society of Chemistry 2011

Entities: Chemical Disease Gene Species

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Year: 2011 PMID： 21892457 PMCID： PMC3805137 DOI： 10.1039/c1cc13409d

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

21 in total

Review 1. Conformational studies of oligosaccharides and glycopeptides: complementarity of NMR, X-ray crystallography, and molecular modelling.

Authors: Mark R Wormald; Andrei J Petrescu; Ya-Lan Pao; Ann Glithero; Tim Elliott; Raymond A Dwek
Journal: Chem Rev Date: 2002-02 Impact factor: 60.622

2. Efficient solid-phase synthesis of a complex, branched N-glycan hexasaccharide: use of a novel linker and temporary-protecting-group pattern.

Authors: Xiangyang Wu; Matthias Grathwohl; Richard R Schmidt
Journal: Angew Chem Int Ed Engl Date: 2002-12-02 Impact factor: 15.336

3. Toward solution-phase automated iterative synthesis: fluorous-tag assisted solution-phase synthesis of linear and branched mannose oligomers.

Authors: Firoz A Jaipuri; Nicola L Pohl
Journal: Org Biomol Chem Date: 2008-05-16 Impact factor: 3.876

4. S-thiazolinyl (STaz) glycosides as versatile building blocks for convergent selective, chemoselective, and orthogonal oligosaccharide synthesis.

Authors: Papapida Pornsuriyasak; Alexei V Demchenko
Journal: Chemistry Date: 2006-08-25 Impact factor: 5.236

5. Linear synthesis of a protected H-type II pentasaccharide using glycosyl phosphate building blocks.

Authors: K R Love; R B Andrade; P H Seeberger
Journal: J Org Chem Date: 2001-11-30 Impact factor: 4.354

6. Ionic catch and release oligosaccharide synthesis (ICROS).

Authors: Anh-Tuan Tran; Richard Burden; Daugirdas T Racys; M Carmen Galan
Journal: Chem Commun (Camb) Date: 2011-03-09 Impact factor: 6.222

7. Orthogonal activation of propargyl and n-pentenyl glycosides and 1,2-orthoesters.

Authors: Srinivasa Rao Vidadala; Shivaji A Thadke; Srinivas Hotha
Journal: J Org Chem Date: 2009-12-04 Impact factor: 4.354

8. Ketone hydrosilylation with sugar silanes followed by intramolecular aglycone delivery: an orthogonal glycosylation strategy.

Authors: Zachary A Buchan; Scott J Bader; John Montgomery
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

Reverse orthogonal strategy for oligosaccharide synthesis.

Review 1. Conformational studies of oligosaccharides and glycopeptides: complementarity of NMR, X-ray crystallography, and molecular modelling.

2. Efficient solid-phase synthesis of a complex, branched N-glycan hexasaccharide: use of a novel linker and temporary-protecting-group pattern.

3. Toward solution-phase automated iterative synthesis: fluorous-tag assisted solution-phase synthesis of linear and branched mannose oligomers.

4. S-thiazolinyl (STaz) glycosides as versatile building blocks for convergent selective, chemoselective, and orthogonal oligosaccharide synthesis.

5. Linear synthesis of a protected H-type II pentasaccharide using glycosyl phosphate building blocks.

6. Ionic catch and release oligosaccharide synthesis (ICROS).

7. Orthogonal activation of propargyl and n-pentenyl glycosides and 1,2-orthoesters.

8. Ketone hydrosilylation with sugar silanes followed by intramolecular aglycone delivery: an orthogonal glycosylation strategy.

9. Oligosaccharide synthesis in microreactors.

Review 10. Biological roles of oligosaccharides: all of the theories are correct.

Review 1. Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

2. Broadening the Scope of the Reverse Orthogonal Strategy for Oligosaccharide Synthesis.

3. Glycosyl Thioimidates as Versatile Building Blocks for Organic Synthesis.

4. Templated Oligosaccharide Synthesis: The Linker Effect on the Stereoselectivity of Glycosylation.

5. Regioselective monodeprotection of peracetylated carbohydrates.