Journal of the Chemical Society. Perkin transactions I p. 2051 - 2060 (1996)
Update date:2022-08-05
Topics:
Hof, Robert P.
Kellogg, Richard M.
Diols 1, which contain adjacent tertiary and primary hydroxy groups, can be selectively mono-acylated at the primary hydroxy group by many lipases in organic solvents. Since the reaction does not take place at the chiral tertiary centre itself, observed enantioselectivities are usually low. Only the combination of one lipase, lipase AKG (Amano, Pseudomonas sp.), with selected substrates gives high enantioselectivities (E 20 to > 200). Also, the solvent and acyl donor employed influences the outcome. On the basis of the results of lipase AKG towards substrates 1 an active site model for this specific lipase has been developed, which can account for the results obtained. Full experimental details on the synthesis of diols 1 and enzymatic preparation of acetates 2 are given. Also, the absolute stereochemistry of the enzymatically prepared diols 1 has been established by independent synthesis from (R)-mandelic acid.
View MoreGuangzhou Reachin Chemical Co., Ltd
Contact:+86-20-37087379 ext.604
Address:A122C-1, Tianyuan Plaza, 401 Tianyuan Rd., Tianhe, Guangzhou, China
Ningbo Hi-tech Zone Nice-Synth Chemical Industry Ltd.
Contact:+86-(574)-81110986
Address:No. 1210, Building 3, Wante Business Centre, Hi-tech Zone, Ningbo
Zhengzhou Xinlian Chemical Tech Co. ,Ltd
Contact:0371-65771781 021-52042910
Address:H Part, Building I, No. 700 Gonglu Road, Pudong New Area, Shanghai
Contact:18698110882
Address:1303 No2 building,LuoMa Garden,YongAn Road,Hexi District,Tianjin city
Hangzhou Eastbiopharm Co.,Ltd.
Contact:+86-571-88931780
Address:Hangzhou,China
Doi:10.1002/adsc.201800267
(2018)Doi:10.1016/0040-4039(96)01408-6
(1996)Doi:10.1016/0040-4039(96)01605-X
(1996)Doi:10.1016/j.ica.2010.05.031
(2010)Doi:10.1002/hlca.200390243
(2003)Doi:10.1007/BF00807079
(1996)
