Literature DB >> 17279267

Dihydroxylation of 2-vinylaziridine: efficient synthesis of D-ribo-phytosphingosine.

Hyo Jae Yoon1, Yong-Woo Kim, Baeck Kyoung Lee, Won Koo Lee, Yongeun Kim, Hyun-Joon Ha.   

Abstract

An efficient and highly stereoselective synthesis of D-ribo-(2S,3S,4R)-phytosphingosine was accomplished in 62% overall yield starting from commercially available (2S)-hydroxymethylaziridine via osmium-catalyzed asymmetric dihydroxylation as a key step.

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Year:  2006        PMID： 17279267     DOI： 10.1039/b612740a

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


  3 in total

1.  Synthesis of truncated analogues of the iNKT cell agonist, α-galactosyl ceramide (KRN7000), and their biological evaluation.

Authors:  Natacha Veerapen; Faye Reddington; Mariolina Salio; Vincenzo Cerundolo; Gurdyal S Besra
Journal:  Bioorg Med Chem       Date:  2010-11-19       Impact factor: 3.641

2.  Preparation of anti-vicinal amino alcohols: asymmetric synthesis of D-erythro-sphinganine, (+)-spisulosine, and D-ribo-phytosphingosine.

Authors:  Ewen D D Calder; Ahmed M Zaed; Andrew Sutherland
Journal:  J Org Chem       Date:  2013-07-03       Impact factor: 4.354

Review 3.  N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds.

Authors:  Iwona E Głowacka; Aleksandra Trocha; Andrzej E Wróblewski; Dorota G Piotrowska
Journal:  Beilstein J Org Chem       Date:  2019-07-23       Impact factor: 2.883
  3 in total

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