Uses
(S)-(+)-Glycidyl Nosylate is a compound useful in organic synthesis.
Chemical Properties
white to light yellow crystal powde
Uses
(S)-(+)-Glycidyl Nosylate (cas# 115314-14-2) is a compound useful in organic synthesis.
Application
(S)-(+)-Glycidyl Nosylate serves as a valuable reagent for synthesizing various compounds, including chiral amines, β-amino alcohols, and β-amino esters. Further, it has played a vital role in synthesizing various bioactive compounds, including peptides and nucleosides.
Synthesis
General procedure for the synthesis of (S)-(+)-m-nitrobenzenesulfonic acid glycidyl ester from 3-nitrobenzenesulfonyl chloride and (R)-oxirane-2-methanol: at -20 °C, m-nitrobenzenesulfonyl chloride (12.6 g, 57 mmol) was slowly added to a solution containing (R)-(+)-glycidol (5.5 g, 74 mmol) and triethylamine (TEA, 10.3 mL. 74 mmol) in a cold solution. The reaction mixture was stirred continuously at -20 °C for 96 hours. Upon completion of the reaction, the reaction solution was filtered and the filtrate was washed sequentially with 10% (w/w) aqueous tartaric acid, saturated saline and deionized water. The washed organic phase was concentrated to afford the target product (S)-(+)-m-nitrobenzenesulfonic acid glycidyl ester in 97% yield. The structure of the product was confirmed by 1H NMR (CDCl3): δ 2.62 (dd, 1H), 2.84 (dd, 1H), 3.22 (m, 1H), 4.07 (dd, 1H), 4.49 (dd, 1H), 7.80 (t, 1H), 8.25 (m, 1H), 8.52 (m, 1H), 8.78 (m, 1H).
References
[1] Angewandte Chemie - International Edition, 2013, vol. 52, # 20, p. 5305 - 5308
[2] Angew. Chem., 2013, vol. 125, # 20, p. 5413 - 5416,4
[3] European Journal of Organic Chemistry, 2014, vol. 2014, # 19, p. 4053 - 4069
[4] Patent: US2004/229900, 2004, A1. Location in patent: Page 14
[5] Organic and Biomolecular Chemistry, 2006, vol. 4, # 16, p. 3067 - 3076
