Triphenylphosphine → 2-acetyl-3-hydroxy-5-methylphenyl 2,3,4,6-tetra-O-acetyl-5-thio-beta-D-glucopyranoside

HRID 2219465Notes

Reaction equation

HRID 2219465 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].[C:25]([C:28]1[C:34](O)=[CH:33][C:32]([CH3:36])=[CH:31][C:29]=1[OH:30])(=[O:27])[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:34]1[CH:33]=[C:32]([CH3:36])[CH:31]=[C:29]([OH:30])[C:28]=1[C:25](=[O:27])[CH3:26])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 104195313,5-Dihydroxy-4-acetyltolueneHCID 116462702,3,4,6-tetra-O-acetyl-5-thio-glucopyranose

Product 1

HCID 692018012-acetyl-3-hydroxy-5-methylphenyl 2,3,4,6-tetra-O-acetyl-5-thio-beta-D-glucopyranosideYield 29.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,3,4,6-Tetra-O-acetyl-5-thio-D-glucopyranose (200 mg, 0.55 mmol), 2-acetyl-5-methylresorcinol (182 mg, 1.10 mmol), triphenylphosphine (288 mg, 1.10 mmol) and toluene (2 mL) were mixed, and to the resulting mixture, diisopropyl azodicarboxylate (40% in toluene, 555 mg) was then slowly added dropwise in ice. After stirring at room temperature for 18 hours, the reaction mixture was concentrated and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:30-50:50) to give 2-acetyl-3-hydroxy-5-methylphenyl 2,3,4,6-tetra-O-acetyl-5-thio-β-D-glucopyranoside (82 mg, 28%) as a light-yellow powder.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=70:30-50:50)

Sources & evidence

ORD record
ord-9dc73a3dcffa4dd8914d7e9f28435303
Source dataset
uspto-grants-2008_08
Patent number
US07414072B2

Reaction notes

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