Triphenylphosphine → 4-[4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)phenyl]-2-(3,4-diethoxyphenyl)-thiazole

HRID 1421960Notes

Reaction equation

HRID 1421960 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[C:15]([O:22][CH2:23][CH3:24])[CH:14]=3)[S:11][CH:12]=2)=[CH:4][CH:3]=1.[C:25]([O:28][C@@H:29]1[C@@H:35]([O:36][C:37](=[O:39])[CH3:38])[C@H:34]([O:40][C:41](=[O:43])[CH3:42])[C@@H:33]([CH2:44][O:45][C:46](=[O:48])[CH3:47])[O:32][C@H:30]1O)(=[O:27])[CH3:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:25]([O:28][C@@H:29]1[C@@H:35]([O:36][C:37](=[O:39])[CH3:38])[C@H:34]([O:40][C:41](=[O:43])[CH3:42])[C@@H:33]([CH2:44][O:45][C:46](=[O:48])[CH3:47])[O:32][C@H:30]1[O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[C:15]([O:22][CH2:23][CH3:24])[CH:14]=3)[S:11][CH:12]=2)=[CH:4][CH:3]=1)(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 11013485beta-D-Glucopyranose, 2,3,4,6-tetraacetateHCID 18707187HCID 18707187, compound

Product 1

HCID 540604894-[4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)phenyl]-2-(3,4-diethoxyphenyl)-thiazoleYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 45 ml of tetrahydrofuran were dissolved 1.5 g of 4-(4-hydroxyphenyl)-2-(3,4-diethoxyphenyl)thiazole, 1.4 g of 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose and 1.3 g of triphenylphosphine. Thereto was added, in small portions at 0° C., a solution of 0.9 g of diethyl azodicarboxylate dissolved in 5 ml of tetrahydrofuran. The mixture was stirred at room temperature for 14 hours. The solvent was removed by distillation. The residue was purified by silica gel column chromatography (elutant: dichloromethane) and recrystallized from ethyl acetate-n-hexane to obtain 1.52 g of 4-[4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)phenyl]-2-(3,4-diethoxyphenyl)thiazole.

Workup

  1. additionThereto was added, in small portions at 0° C.
  2. customThe solvent was removed by distillation
  3. customThe residue was purified by silica gel column chromatography (elutant: dichloromethane)
  4. customrecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-830f54aad7ba473ebb2a655e3dcf7b2c
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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