Water → Allyl 6-O-trityl-alpha-D-glucopyranoside

反応式

[O:1]([CH2:13][CH:14]=[CH2:15])[C@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[C:16]1([C:22](Cl)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>N1C=CC=CC=1>[C:22]([O:12][CH2:11][C@H:9]1[O:10][C@H:2]([O:1][CH2:13][CH:14]=[CH2:15])[C@H:3]([OH:4])[C@@H:5]([OH:6])[C@@H:7]1[OH:8])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

参加物

実験手順

A solution of allyl α-D-glucopyranoside (1) (prepared according to R. E. Wing, J. N. BeMiller, Carbohydr. Res. 1969, 10, 441) (12.5 g, 56.8 mmol) and triphenylmethyl chloride (20.0 g, 71.7 mmol) in dry pyridine (120 ml) was stirred at r.t. for 12 h, and at 60° for 1 h. After the addition of triphenylmethyl chloride (12.0 g, 43.0 mmol), the solution was stirred at 60° until all starting material has disappeared (3-4 h). H2O (120 ml) was added to the still warm solution. Extraction with EtOAc, extraction of the combined org. layers with 1M aq. H2SO4 and brine, evaporation of the organic layer and FC (400 g SiO2, toluene/actone 2:1→toluene/acetone 1:1) gave 23.3 g (90%) of 2. Grey glassy solid.