Helvetica Chimica Acta p. 1467 - 1487 (1981)
Update date:2022-08-04
Topics: Enantiomerically pure Tartaric acid Functional Groups Experimental Malic Acid Synthetic Building Blocks C-Atoms β-Hydroxy-butanoic Acid
Hungerbuehler, Ernst von
Seebach, Dieter
Wasmuth, Daniel
The pool of chiral, non-racemic electrophilic building blocks, which are available from simple natural products in both enantiomeric forms is enlarged by the epoxides 3, 5, and 10, by the tosylate 12a, and by the aldehydes 18 (cf. symbols A-D, 14, and Scheme 1).Key steps of the conversions leading from hydroxyacids to the building blocks are: epoxide-opening by triethylborohydride (1 --> 2a) and tosylate reduction (12a --> 12b); the Mitsunobu inversion (2a --> 4a); the reduction of (R,R)-tartaric ester to (R)-malic ester by NBS (N-bromosuccinimide) opening of the benzaldehyde acetal 8 and tin hydride reduction (6c -->7c); the enantiomer enrichment of optically active ethyl β-hydroxy-butanoate through the crystalline dinitrobenzoate 21b.Detailed procedures are given for large scale preparations of the key intermediates.The enantiomeric purities of the building blocks are secured by correlations.
View MoreContact:18669908765
Address:Zibo City, Shandong Province, P.R.China
Contact:+86-513-80923002
Address:Suzhou Road 8,Beixin,Qidong,Jiangsu province,P.R.226221,China
SuZhou Bichal Biological Technology CO.,LTD
Contact:+86-512-68051130
Address:NO.32 huoju road HI-TECH Industrial development zone SuZhou China
Compro Shijiazhuang Fine Chemical Co., Ltd
Contact:0086-311-89689838
Address:Economic and Technological Development Zone of Shijiazhuang,Hebei
Hubei Lingsheng Pharmaceuticals Co., Ltd.
Contact:+86-0710-3538058
Address:Xiangyang City Xiangcheng Economic Development Zone, Hubei Province
Doi:10.1080/10587250008023819
(2000)Doi:10.1021/acs.joc.1c00606
(2021)Doi:10.1016/j.jorganchem.2004.07.041
(2004)Doi:10.1016/S0040-4039(00)99861-7
(1984)Doi:10.1002/anie.200460475
(2004)Doi:10.1248/cpb.33.497
(1985)