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 MoreABA Chemicals (Shanghai) Limited
Contact:021- 5115 9199-232
Address:Suite 18D, #201 Ningxia Road,
Heliosense Biotechnologies, Inc.
Contact:+86-592-5667290
Address:Xiamen Torch Hi-tech Zone Venture Weiye Building S506
Jiangxi Dongbang Pharmaceutical Co., Ltd.
Contact:+86-795-4433603, 4433388
Address:Fengxin Industrial Park, Fengxin County, Jiangxi Province, P.R.C
XI'AN CHUKANG BIOTECHNOLOGY CO.,LTD
Contact:29-63685658 63685359
Address:Room 3-1202,Building 1,Oriental oasis,East of Xianning Road,Xi'an,Shaanxi 710043 P.R.China
MTT Pharma & Bio-technology Co.,Ltd(expird)
Contact:+86-21-58407925
Address:Room2019, Building C, Tomson Center, No.158, Zhang Yang Road, Shanghai, 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)