Journal of Organic Chemistry p. 4637 - 4642 (1989)
Update date:2022-09-26
Topics:
Guivisdalsky, Pedro N.
Bittman, Robert
A short, chiral synthesis of unnatural, cytotoxic ether-linked phospholipids is reported in which the key step is the very high regio- and stereospecific nucleophilic opening of the p-toluenesulfonate (1a, 1b) or tert-butyldiphenylsilyl ether (6a, 6b) derivatives of (R)- or (S)-glycidol with 1-hexadecanol using boron trifluoride etherate as catalyst.The enantiomeric excess of the ring-opened products was >94percent, as judged by 1H NMR and chiral HPLC analysis of the Mosher ester derivatives, indicating that ring opening of 1 and 6 proceeds without significant loss of optical purity.The synthetic strategy of using optically active glycidyl derivatives as the precursor of the glycerol backbone permits the desired enantiomers of 1(3)-O-2-O-methylphosphocholines (5a, 5b) to be generated in good yield and high optical purity from the ring-opened intermediates (2, 7) in three steps without the use of protecting groups.
View MoreFujian Wanke Pharmaceutical Co., LTD.
Contact:+86-598-5026002
Address:Economic development zone,jiangle county
TIANJIN NORTH JINHENG CHEMICAL PLANT.
Contact:0086-22-59952083
Address:DongShigu Country In JiXian TianJin China
Hunan Dinuo Pharmaceutical Co.,Ltd.
Contact:86-731-88280100*8561
Address:Bio-pharmaceutical industrial park, Liuyang, Hunan, China
Wuxi D-Stone International Co., Ltd.
Contact:+86-510-82740567
Address:21F Hengtong Int'l Centre, 215Zhongshan Road, Wuxi, Jiangsu,China
Chongqing Rong&Quan Pharmaceutical Technology Co. , Ltd.
Contact:86-023-65268721
Address:No. 7, Manshanhong Village, Pingdingshan, Shapingba District, Chongqing Province, China
Doi:10.1039/c0cc00038h
(2010)Doi:10.1016/j.tetlet.2011.07.032
(2011)Doi:10.1002/zaac.200900170
(2009)Doi:10.1016/j.ejmech.2010.03.008
(2010)Doi:10.1016/j.ejmech.2010.03.026
(2010)Doi:10.1021/ma100814v
(2010)