Journal of Organic Chemistry p. 5294 - 5299 (1986)
Update date:2022-08-03
Topics: Synthesis Chiral Organic synthesis Experimental Practical D-mannitol
Mulzer, Johann
Angermann, Alfred
Schubert, Boris
Seilz, Carsten
A short and practical synthesis of five D-α-amino acids is described from D-mannitol as the chiral educt.The key steps in the sequence are (a) the erythro-selective addition of organometals to (R)-2,3-O-isopropylideneglyceralaldehyde, (b) the Mitsunobu inversion substituting N-phthalimide for hydroxyl, and (c) acetonide hydrolysis and glycol cleavage to give the N -phthaloyl-(R)-α-aminoaldehydes 7.These are oxidized under Jones conditions to give the N-protected amino acids 8.The examples investigated (alanine, aminobutyric acid, norvaline, and allyl- and vinylglycine) demonstrate the general applicability of the method.
View MoreXiamen Kaijia Imp & Exp Co., Ltd.
Contact:86-592-5101177
Address:Room406 Luhui Building No. 65 Haitian Road Huli Xiamen,China.
NINGBO PANGS CHEM INT’L CO., LTD.
Contact:+86-0574-27666801
Address:Floor 21, Building 11, Xintiandi, No. 689, Shijiroad, Ningbo, Zhejiang, China
Contact:86-898-65311214
Address:Room 102, BLDG. 68 Jiangnan City, No. 66 Heping Road,Haikou, Hainan, China
puyang hongda shengdao new material co.,ltd.
Contact:+86-393- 4896278
Address:No.29 East Zhongyuan Road
Fuxin Jintelai Fluorin Chemical Co., Ltd.
Contact:+86-0418-8229599
Address:, 7th Huagong Road, Fluorine industry development zone (Yimatu Town,Fumeng County),Fuxin City, Liaoning Province, China
Doi:10.1002/anie.202006278
(2020)Doi:10.1248/cpb.37.190
(1989)Doi:10.1021/ja00988a069
(1967)Doi:10.1021/ja8039025
(2008)Doi:10.1134/S1070328413020103
(2013)Doi:10.1002/ardp.18972350407
(1897)