Triphenylphosphine → 3-hydroxy-2-(4-ethylbenzyl)phenyl 2,3,4,6-tetra-O-acetyl-5-thio-beta-D-glucopyranoside

HRID 1297548Notes

Reaction equation

HRID 1297548 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[S:8][CH:6]1[OH:7])(=[O:3])[CH3:2].[CH2:25]([C:27]1[CH:41]=[CH:40][C:30]([CH2:31][C:32]2[C:38](O)=[CH:37][CH:36]=[CH:35][C:33]=2[OH:34])=[CH:29][CH:28]=1)[CH3:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[C:1]([O:4][C@@H:5]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[S:8][C@H:6]1[O:7][C:38]1[CH:37]=[CH:36][CH:35]=[C:33]([OH:34])[C:32]=1[CH2:31][C:30]1[CH:29]=[CH:28][C:27]([CH2:25][CH3:26])=[CH:41][CH:40]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 116462702,3,4,6-tetra-O-acetyl-5-thio-glucopyranoseHCID 230727622-(4-Ethylbenzyl)resorcinol

Product 1

HCID 692015803-hydroxy-2-(4-ethylbenzyl)phenyl 2,3,4,6-tetra-O-acetyl-5-thio-beta-D-glucopyranosideYield 16.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,3,4,6-Tetra-O-acetyl-5-thio-D-glucopyranose (1.29 g, 3.54 mmol), 2-(4-ethylbenzyl)resorcinol (2.42 g, 10.6 mmol), triphenylphosphine (1.86 g, 7.09 mmol) and toluene (13 mL) were mixed, and to the resulting mixture, diisopropyl azodicarboxylate (40% in toluene, 3.58 g) was then slowly added dropwise in ice. After stirring at room temperature for 24 hours, the reaction mixture was concentrated and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=65:35–50:50) to give a crude product of 3-hydroxy-2-(4-ethylbenzyl)phenyl 2,3,4,6-tetra-O-acetyl-5-thio-β-D-glucopyranoside (338 mg). To a mixture of this crude product (338 mg) and pyridine (2 mL), acetic anhydride (0.5 mL) was added at room temperature. After stirring at room temperature for 20 hours, water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic phase was washed with saturated aqueous sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give the titled compound (134 mg, 6%) as a light-yellow gum.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=65:35–50:50)

Sources & evidence

ORD record
ord-bb507ecce11247e38120e4876fcf08b5
Source dataset
uspto-grants-2007_07
Patent number
US07250522B2

Reaction notes

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