Water → 2-(2,3,4,6-Tetra-o-acetyl-beta-d-glucopyranosyloxy)-3',4',5'-tribenzyloxyacetophenone

HRID 1894921Notes

Reaction equation

HRID 1894921 reaction equation
I[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:7]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=1)=[O:4].[C:35]([O:38][C@@H:39]1[C@@H:45]([O:46][C:47](=[O:49])[CH3:48])[C@H:44]([O:50][C:51](=[O:53])[CH3:52])[C@@H:43]([CH2:54][O:55][C:56](=[O:58])[CH3:57])[O:42][C@H:40]1[OH:41])(=[O:37])[CH3:36].[H-].[Na+].O>C(Cl)Cl>[C:35]([O:38][C@@H:39]1[C@@H:45]([O:46][C:47](=[O:49])[CH3:48])[C@H:44]([O:50][C:51](=[O:53])[CH3:52])[C@@H:43]([CH2:54][O:55][C:56](=[O:58])[CH3:57])[O:42][C@H:40]1[O:41][CH2:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:7]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=1)=[O:4])(=[O:37])[CH3:36]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydride2×HCID 11013485beta-D-Glucopyranose, 2,3,4,6-tetraacetateHCID 576727822-Iodo-3',4',5'-tribenzyloxyacetophenone

Product 1

HCID 159407112-(2,3,4,6-Tetra-o-acetyl-beta-d-glucopyranosyloxy)-3',4',5'-tribenzyloxyacetophenone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Iodo-3′,4′,5′-tribenzyloxyacetophenone (20) (5.64 g, 10 mmol) and β-D-glucose-2,3,4,6-tetraacetate (8) (4.18 g, 12 mmol) was dissolved in dry DCM (50 mL) and sodium hydride (0.48 g, 20 mmol) (0.8 g 60% NaH suspension in oil)) was added in small portions. The reaction mixture was allowed to be stirred at room temperature overnight. Excess of sodium hydride was decomposed by addition of suitable amount water. Dichloromethane was removed under vacuum in order to simplify the work up. Water (100 mL) was added and the water phase extracted with diethyl ether (4×75 mL). The organic layers were combined and washed with water (2×50 mL), dried (MgSO4) and evaporated to give a dark viscous oil. The product was isolated by dry flash chromatography (PE/EtOAc 6:4). Recrystallisation from a mixture of methylcyclohexane and ethyl acetate afforded the desired compound as white crystals, m.p. 156-158° C. Yield 5.1 g (65%).

Workup

  1. customDichloromethane was removed under vacuum in order
  2. additionWater (100 mL) was added
  3. extractionthe water phase extracted with diethyl ether (4×75 mL)
  4. washwashed with water (2×50 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give a dark viscous oil
  8. customThe product was isolated
  9. dry with materialby dry flash chromatography (PE/EtOAc 6:4)
  10. customRecrystallisation
  11. additionfrom a mixture of methylcyclohexane and ethyl acetate

Sources & evidence

ORD record
ord-d62f096543a84a6cb270f4216a31f53d
Source dataset
uspto-grants-2013_08
Patent number
US08513395B2

Reaction notes

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