330555-58-3Relevant academic research and scientific papers
A simple three-step method for preparing homochiral 5-trityloxymethyl-2-oxazolidinones from optically active 3-hydroxy-γ-butyrolactones
Wang, Guijun,Hollingsworth, Rawle I
, p. 4429 - 4432 (2000)
A simple high-yield three-step route to O-tritylated optically active 5-hydroxymethyl oxazolidinones from optically active 3-hydroxy-γ-butyrolactones is described. The key intermediate is the 4-O-trityl ether of homochiral 3,4-dihydroxybutyramide, which is obtained in quantitative yield from 3-hydroxy-γ-butyrolactone by treatment with ammonia. It is readily transformed to the oxazolidinone by Hoffmann rearrangement in a two-phase system. The carbonyl group in the oxazolidinone is derived from C-1 of the amide, and a separate carbonylation reaction is not required. Oxazolidinones are key compounds in drug synthesis especially in the areas of antibacterials and behavior disorder therapy.
Gold(I)-catalyzed, one-pot, oxidative formation of 2,4-disubstituted thiazoles: Application to the synthesis of a pateamine-related macrodiolide
Xu, Tao,Cuyamendous, Claire,Brown, Sarah L.,Andreassend, Sarah K.,Cumming, Hemi,Evans, Gary B.,Teesdale-Spittle, Paul H.,Harvey, Joanne E.
supporting information, (2021/05/04)
Thiazoles are important heterocyclic motifs in many target molecules. Extension of a reported gold(I)-catalyzed oxidative coupling of alkynes and thioamides to the synthesis of functionalized thiazole-containing products is presented, including the compatibility of this reaction with ester, protected hydroxyl, alkene and thioether groups. The utility of this one-pot process is demonstrated in the preparation of the thiazole-containing macrodiolide of a simplified analogue of pateamine A.
Lipase-mediated resolution of 3-hydroxy-4-trityloxybutanenitrile: synthesis of 2-amino alcohols, oxazolidinones and GABOB
Kamal, Ahmed,Khanna, G.B. Ramesh,Krishnaji,Ramu
, p. 1281 - 1289 (2007/10/03)
Lipase-mediated kinetic resolution of 3-hydroxy-4-trityloxybutanenitrile gave the (S)-alcohol and (R)-acetate in good yields and high enantioselectivities. The resolution using Pseudomonas cepacia lipase (Burkholderia cepacia) immobilized on modified cera
New synthesis of chiral 1,3-oxazinan-2-ones from carbohydrate derivatives
Ella-Menye, Jean-Rene,Sharma, Vibha,Wang, Guijun
, p. 463 - 469 (2007/10/03)
(Chemical Equation Presented) Chiral 1,3-oxazinan-2-ones are useful intermediates in synthesizing pharmaceutical compounds and amino alcohols. In this paper, we report a new synthetic method to chiral 6-hydroxymethyl 1,3-oxazinan-2-ones and their analogue
PROCESS FOR THE PREPARATION OF OXAZOLIDINONES AND METHOD OF USE THEREOF
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Page 46, (2010/02/06)
A process for preparing N-(substituted)-C-- (substituted methyl)-oxazolidinones, C-(substituted methyl)-oxazolidinones, and N-(substituted)-C-- (substituted ethyl)-oxazolidinones, preferably chiral, from optically active C-(protected oxymethyl)- oxazolidi
