Literature DB >> 21895005

Scalable synthesis of enantiomerically pure syn-2,3-dihydroxybutyrate by Sharpless asymmetric dihydroxylation of p-phenylbenzyl crotonate.

Daniel J Smaltz1, Andrew G Myers.   

Abstract

An efficient four-step synthetic route to the useful chiral building block (2R,3S)-dihydroxybutyric acid acetonide in >95% ee is detailed. The sequence is readily scaled, requires no chromatography, and allows for efficient recycling of p-phenylbenzyl alcohol, an expedient for enantio- and diastereoenrichment by recrystallization.

Entities:  

Mesh：

Substances：

Year:  2011        PMID： 21895005      PMCID： PMC3193550          DOI： 10.1021/jo2016746

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


  3 in total

1.  Axenomycins. I. The structure of chromophore and sugar moieties.

Authors:  F Arcamone; W Barbieri; G Franceschi; S Penco; A Vigevani
Journal:  J Am Chem Soc       Date:  1973-03-21       Impact factor: 15.419

2.  Synthesis of 1-N-(D-threo- and racemic erythro-3-amino-2-hydroxybutanoyl)-2',3'-dideoxykanamycin A.

Authors:  E Umemura; T Tsuchiya; S Umezawa
Journal:  J Antibiot (Tokyo)       Date:  1988-04       Impact factor: 2.649

3.  Total synthesis of potent antifungal marine bisoxazole natural products bengazoles A and B.

Authors:  James A Bull; Emily P Balskus; Richard A J Horan; Martin Langner; Steven V Ley
Journal:  Chemistry       Date:  2007       Impact factor: 5.236
  3 in total
  1 in total

1.  Diastereoselective additions of allylmetal reagents to free and protected syn-α,β-dihydroxyketones enable efficient synthetic routes to methyl trioxacarcinoside A.

Authors:  Daniel J Smaltz; Jakub Švenda; Andrew G Myers
Journal:  Org Lett       Date:  2012-03-09       Impact factor: 6.005
  1 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.