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Literature DB >> 18578494

One-pot synthesis of oligosaccharides by combining reductive openings of benzylidene acetals and glycosylations.

Yusuf Vohra¹, Mahalakshmi Vasan, Andre Venot, Geert-Jan Boons.

Abstract

Combining triflic acid-promoted glycosylations of trichloroacetimidates with reductive opening of benzylidene acetals with triflic acid and triethylsilane as one-pot procedures provides access to a wide range of disaccharides and 2,4- and 3,4-branched trisaccharides.

Entities: Chemical

Mesh：

Substances：

Year: 2008 PMID： 18578494 PMCID： PMC2814312 DOI： 10.1021/ol801076w

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

21 in total

1. 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

2. A general strategy for stereoselective glycosylations.

Authors: Jin-Hwan Kim; Hai Yang; Jin Park; Geert-Jan Boons
Journal: J Am Chem Soc Date: 2005-08-31 Impact factor: 15.419

3. Stereoselective glycosylation reactions with chiral auxiliaries.

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Journal: Angew Chem Int Ed Engl Date: 2005-01-28 Impact factor: 15.336

4. Nothing in glycobiology makes sense, except in the light of evolution.

Authors: Ajit Varki
Journal: Cell Date: 2006-09-08 Impact factor: 41.582

Review 5. Post-translational modifications in the context of therapeutic proteins.

Authors: Gary Walsh; Roy Jefferis
Journal: Nat Biotechnol Date: 2006-10 Impact factor: 54.908

6. Use of fluorobenzoyl protective groups in synthesis of glycopeptides: beta-elimination of O-linked carbohydrates is suppressed.

Authors: P Sjölin; J Kihlberg
Journal: J Org Chem Date: 2001-05-04 Impact factor: 4.354

7. Tandem catalysis for a one-pot regioselective protection of carbohydrates: the example of glucose.

Authors: Antoine Français; Dominique Urban; Jean-Marie Beau
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

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

Review 9. Synthesis and medical applications of oligosaccharides.

Authors: Peter H Seeberger; Daniel B Werz
Journal: Nature Date: 2007-04-26 Impact factor: 49.962

10. Regioselective one-pot protection of carbohydrates.

Authors: Cheng-Chung Wang; Jinq-Chyi Lee; Shun-Yuan Luo; Suvarn S Kulkarni; Yu-Wen Huang; Chia-Chen Lee; Ken-Lien Chang; Shang-Cheng Hung
Journal: Nature Date: 2007-04-19 Impact factor: 49.962

7 in total

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Authors: Fatima Enam; Thomas J Mansell
Journal: J Ind Microbiol Biotechnol Date: 2019-06-14 Impact factor: 3.346

2. Rapid assembly of oligosaccharides: a highly convergent strategy for the assembly of a glycosylated amino acid derived from PSGL-1.

Authors: Yusuf Vohra; Therese Buskas; Geert-Jan Boons
Journal: J Org Chem Date: 2009-08-21 Impact factor: 4.354