Bulletin of the Chemical Society of Japan p. 2515 - 2525 (1984)
Update date:2022-08-16
Topics:
Sato
Hayakawa
Noyori
A stereocontrolled, general synthesis of chiral C-nucleosides has been achieved through a common lactonic C- beta -glycoside intermediate which is readily obtainable from non-carbohydrate materials. The optically pure lactone having the natural D configuration is obtained through optical resolution of the seco acid by the Pirkle's method followed by relactonization. alpha -Aminomethylenation of the lactone with t-C//4H//9OCH left bracket N(CH//3 )//2 right bracket //2 yields 2-(2,3-0-isopropylidene- beta -D-ribofuranosyl)-2-(dimethylaminomethylene)acetic acid lactone, which undergoes base-assisted condensation with urea followed by deprotection to furnish naturally occurring pseudouridine. Analogously, construction of heterocycles using thiourea and guanidine converts the aminomethylene lactone to unnatural pyrimidine C-nucelosides, 2-thiopseudouridine and pseudoisocytidine, respectively.
View MoreHuangshan Honghui Pharm Technology Co., Ltd.
website:http://www.honghuichem.com
Contact:18855958372
Address:Qingshan Wan No.1,Nanyuan Kou,SheXian Huangshan City,Anhui Province
QINGDAO TAOSIGN INTERNATIONAL TRADE CO.,LIMITED
Contact:+86-0532-82683616
Address:RM1402, Doublestar Seacoase 7#, No. 5 Guizhou Road, Qingdao, Shandong, China
Contact:+86-575-82733999 0575-82732999
Address:hangzhou gulf fine chemical zone,shangyu city,zhejiang province
Xuzhou Tianrun Chemical Co.,Ltd
website:http://www.tianrunchem.cn
Contact:86-516-83832636
Address:fuxing road
Yixing Bluwat Chemicals Co., Ltd.
Contact:+86 510 87821568
Address:Yongan Road, Yixing Chemical Industrial Park, Yixing, Jiangsu, China
Doi:10.1021/acs.jafc.9b00027
(2019)Doi:10.1002/chem.202001214
(2020)Doi:10.1007/BF00958268
(1990)Doi:10.1039/F29858101695
()Doi:10.1002/hlca.200490140
(2004)Doi:10.1021/ja01386a024
(1929)