Carbohydrate Research p. 195 - 206 (1994)
Update date:2022-09-26
Topics:
Bols, Mikael
Grubbe, Helle
Jespersen, Tina M.
Szarek, Walter A.
(Benzyloxymethyl)lithium, generated in situ from butyllithium and (benzyloxymethyl)tri-n-butylstannane, was found to be an efficient reagent for the monohydroxymethylation of aldono 1,4-lactones to form ketoses.Thus, 4-hydroxy butanoic-1,4-lactone, 2-deoxy-2-fluoro-3,5-di-O-(methoxymethyl)-D-arabinono-1,4-lactone, 2,3,5-tri-O-(methoxymethyl)-D-arabinono-1,4-lactone, 5-O-(methoxymethyl)-2,3-O-methylidene-D-ribono-1,4-lactone, 2,3,5,6-tetra-O-(methoxymethyl)-D-altrono-1,4-lactone, 2,3:5,6-di-O-isopropylidene-D-gulono-1,4-lactone and 2,3-O-isopropylidene-L-erythrono-1,4-lactone were respectively converted to 1-benzyloxy-5-hydroxy-2-pentanone, 1-O-benzyl-3-deoxy-3-fluoro-4,6-di-O-(methoxymethyl)-D-fructofuranose, 1-O-benzyl-3,4,6-tri-O-(methoxymethyl)-D-fructofuranose, 1-O-benzyl-6-O-(methoxymethyl)-2,3-O-methylidene-D-psicofuranose, 1-O-benzyl-3,4,6,7-tetra-O-(methoxymethyl)-D-altro-heptulofuranose, 1-O-benzyl-3,4:6,7-di-O-isopropylidene-D-gulo-heptulofuranose, and 1-O-benzyl-3,4-O-isopropylidene-L-erythro-pentulofuranose in 63-81percent yields.By deprotection of 1-O-benzyl-3-deoxy-3-fluoro-4,6-di-O-(methoxymethyl)-D-fructose, 3-deoxy-3-fluoro-D-fructose was prepared for the first time.
View MoreLIAOYANG WANRONG CHEMICALS COMPANY LIMITED
Contact:86-419-2390789
Address:XINLI VILLAGE , DONG NINGWEI COUNTY,TAIZIHE DISTRICT, LIAOYANG , LIAONING
Laizhou City Laiyu Chemical CO.,Ltd
Contact:+86-535-2719337/2719339
Address:Chenggang road zhuyou laizhou City Shangdong China
Nanjing Vincero International Trading Co.,Ltd
Contact:8618936897229
Address:NO.68, ZhuShan Road, JiangNing WanDa Plaza, Building E Room 1703
ZHEJIANG JIANYE CHEMICAL CO.,LTD.
Contact:86-571-64149273,64149234
Address:No. 48, Fuxi Road, Meicheng Town
HANGZHOU PANYU CHEMICAL CO.,LIMITED
Contact:+86-571-86578491
Address:Rm 605, NO.1870 Binsheng Road,Binjiang Dist, Hangzhou, China
Doi:10.1016/j.jfluchem.2012.08.002
(2012)Doi:10.1016/j.tet.2012.09.049
(2012)Doi:10.1134/S1070363212100027
(2012)Doi:10.1016/j.bmcl.2012.10.045
(2012)Doi:10.1021/jo3022567
(2012)Doi:10.1016/j.tet.2012.10.068
(2013)