Literature DB >> 19413276

Efficient method for the preparation of peracetylated Neu5Ac2en by flash vacuum pyrolysis.

Evan J Horn1, Jacquelyn Gervay-Hague.   

Abstract

Peracetylated Neu5Ac2en methyl ester, an intermediate in the synthesis of the influenza neuraminidase inhibitor Relenza, has been synthesized in high yields from peracetylated Neu5Ac methyl ester by flash vacuum pyrolysis. Mechanistic evidence including deuterium labeled studies and DFT (B3LYP) calculations suggest this transformation proceeds via an intramolecular syn-elimination.

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Year:  2009        PMID: 19413276      PMCID: PMC4557971          DOI: 10.1021/jo900224t

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  4 in total

Review 1.  Chemical diversity in the sialic acids and related alpha-keto acids: an evolutionary perspective.

Authors:  Takashi Angata; Ajit Varki
Journal:  Chem Rev       Date:  2002-02       Impact factor: 60.622

2.  An empirical study of the effect of the variables in a flash vacuum pyrolysis (FVP) experiment.

Authors:  Emma F Duffy; Jonathan S Foot; Hamish McNab; Andrew A Milligan
Journal:  Org Biomol Chem       Date:  2004-08-24       Impact factor: 3.876

3.  A facile synthesis of 2-deoxy-2,3-didehydroneuraminic acid derivatives.

Authors:  K Ikeda; K Konishi; K Sano; K Tanaka
Journal:  Chem Pharm Bull (Tokyo)       Date:  2000-01       Impact factor: 1.645

4.  Investigation into an efficient synthesis of 2,3-dehydro-N-acetyl neuraminic acid leads to three decarboxylated sialic acid dimers.

Authors:  Evan J Horn; Jonel P Saludes; Jacquelyn Gervay-Hague
Journal:  Carbohydr Res       Date:  2008-02-02       Impact factor: 2.104

  4 in total
  2 in total

1.  One-pot SSA-catalyzed β-elimination: an efficient and inexpensive protocol for easy access to the glycal of sialic acid.

Authors:  Erickson M Paragas; I Abrrey Monreal; Chris M Vasil; Jonel P Saludes
Journal:  Carbohydr Res       Date:  2014-09-17       Impact factor: 2.104

2.  Probing the influence of protecting groups on the anomeric equilibrium in sialic acid glycosides with the persistent radical effect.

Authors:  Pavan K Kancharla; Takayuki Kato; David Crich
Journal:  J Am Chem Soc       Date:  2014-04-01       Impact factor: 15.419

  2 in total

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