Journal of Organic Chemistry p. 3887 - 3894 (1992)
Update date:2022-09-26
Topics:
Beach, J. Warren
Kim, Hea O.
Jeong, Lak S.
Nampalli, Satyanarayana
Islam, Qamrul
et al.
A general total synthesic method for the stereocontrolled synthesis of 2',3'-dideoxy- as well as 2',3'-didehydro-2',3'-dideoxynucleosides is presented.Introduction of an α-phenylselenenyl group at the 2-position of 2,3-dideoxyribosyl acetate directs the glycosyl bond formation to give >/=95percent β-isomer.This 2'-phenylselenenyl nucleoside may be converted to either the 2',3'-dideoxynucleoside by treatment with n-Bu3SnH and Et3B at room temperature or to the unsaturated derivative by treatment with H2O2/cat. pyridine.The application of this method to the syntheses of pyrimidines (ddU, ddT, ddC), 6-substituted purines (ddA, ddI, 6-chloro-ddP, N6-Me-ddA), and 2,6-disubstituted purines (2-F-ddA, 6-chloro-2-amino-ddP) as well as selected 2',3'-didehydro-2',3'-dideoxy derivatives is reported.
View MoreJinan Jinguilin Chemical Co.,Ltd
Contact:+86-531-81188412
Address:3rd floor of Torch Building, Huanyuan Rd, City of Jinan
Taizhou Huading Chemical Co.,Ltd(expird)
Contact:+86-576-88583898
Address:Economic&Technology development zone,Taizhou City,Zhejiang Province,China
Cerametek Materials(ShenZhen)Co., Ltd.
Contact:+86-755-2324.2554
Address:A3-#9, YongChuan Street, Suite 501
TIANJIN FESTO CHEMICAL CO.,LTD(expird)
Contact:86-22-25814570
Address:No.12th,5th Ave.,TEDA,Tianjin,China
Rudong Zhenfeng Yiyang Chemical Co., Ltd.
Contact:0513-84573047
Address:South Fengli Town, Rudong County, Jiangsu Province, China
Doi:10.1002/hlca.201200557
(2012)Doi:10.1016/j.tetlet.2012.12.056
(2013)Doi:10.1080/15533174.2012.680145
(2013)Doi:10.1055/s-1992-26139
(1992)Doi:10.1016/j.carres.2012.11.008
(2013)Doi:10.1039/c3md00185g
(2013)