Tetrahedron p. 5807 - 5824 (1990)
Update date:2022-08-05
Topics:
Casiraghi, Giovanni
Colombo, Lino
Rassu, Gloria
Spanu, Pietro
Fava, Giovanna Gasparri
Belicchi, Maria Ferrari
The BF3-promoted addition of 2-(trimethylsiloxy)furan to three carbon synthons derived from D- and L-glyceraldehyde, D- and L-serinal, and imines thereof furnishes C7 α,β-unsaturated 2,3-dideoxy-aldonolactone derivatives in high yield, with very high level of diastereoselection.In all the cases, compounds having 4,5-threo:5,6-erythro relative stereodisposition preferentially emerge from the reactions, accompanied by only marginal amounts of 4,5-erythro:5,6-threo epimers.An empirical rule for the rapid assignment of the configuration at C-4 (γ-carbon) of γ-substituted unsaturated and saturated β-butyrolactones is given, based upon the sign of the optical rotation values.
View MoreFOSHAN NANHAI ZHONGNAN PHARMACEUTICAL FACTORY
Contact:0086-0757-85609331
Address:XIAHENGTIAN INDUSTRIAL ZONE,SHAYONG VILLAGE,LISHUI TOWN
Wuhan Yitongtai Science and Technology Co.,Ltd.
Contact:+86-27-88933550
Address:27th Fl. Bldg. 1, Shuian International Mansion, Heping Ave, Wuhan, Hubei, China
Contact:
Address:
WUXI KINGHAN BIO-MEDICAL&CHEMICAL INC.
Contact:13861062998
Address:Room 1316,No.1619 Huishan Avenue,Wuxi,China
Beijing Stable Chemcial Co.ltd
Contact:86-10-63785052
Address:A1301 Technological Edifice. No.4 FuFeng Road,FengTai District, Beijing. China
Doi:10.1007/s00706-011-0521-7
(2011)Doi:10.1021/ja205046h
(2011)Doi:10.3987/COM-10-12096
(2011)Doi:10.1073/pnas.1015267108
(2011)Doi:10.1016/j.jorganchem.2004.07.037
(2004)Doi:10.1021/jacs.1c06125
(2021)