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

HRID 53837Notes

Reaction equation

HRID 53837 reaction equation
[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

Participants

5

Reactant 3

HCID 962WaterHCID 6456Trityl chloride2×HCID 10878666alpha-D-Glucopyranose, O-2-propenyl-

Product 1

HCID 21591574Allyl 6-O-trityl-alpha-D-glucopyranosideYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  1. custom(3-4 h)
  2. extractionExtraction
  3. extractionwith EtOAc, extraction of the combined org
  4. customlayers with 1M aq. H2SO4 and brine, evaporation of the organic layer and FC (400 g SiO2, toluene/actone 2:1→toluene/acetone 1:1)

Sources & evidence

ORD record
ord-6430a74b981e413c9d24d5cec2acc2d1
Source dataset
uspto-grants-1997_04
Patent number
US05621002

Reaction notes

Loading…