Acetic Acid → HCID 86605975, compound

HRID 502090Notes

Reaction equation

HRID 502090 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([C@:26]2([O:44][C@H:43]([CH2:45][O:46][C:47](=[O:49])[CH3:48])[C@@H:38]([O:39][C:40](=[O:42])[CH3:41])[C@H:33]([O:34][C:35](=[O:37])[CH3:36])[C@H:28]2[O:29][C:30](=[O:32])[CH3:31])[OH:27])=[CH:22][C:21]=1[CH2:50][C:51]1[CH:56]=[CH:55][C:54]([O:57][Si](C(C)(C)C)(C)C)=[CH:53][CH:52]=1.C(O)(=O)C.C(OCC)(=O)C>O1CCCC1.O>[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([C@:26]2([O:44][C@H:43]([CH2:45][O:46][C:47](=[O:49])[CH3:48])[C@@H:38]([O:39][C:40](=[O:42])[CH3:41])[C@H:33]([O:34][C:35](=[O:37])[CH3:36])[C@H:28]2[O:29][C:30](=[O:32])[CH3:31])[OH:27])=[CH:22][C:21]=1[CH2:50][C:51]1[CH:52]=[CH:53][C:54]([OH:57])=[CH:55][CH:56]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 86605976HCID 86605976, compound

Product 1

HCID 86605975HCID 86605975, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2.02 ml of a 1 M solution of tetrabutylammoniumfluoride in tetrahydrofuran are added to a solution of 1.3 g 1-methyl-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-2-[4-(tert-butyl-dimethyl-silyloxy)-benzyl]-benzene and 0.12 ml acetic acid in 10 ml of tetrahydrofuran. The solution is stirred for 30 min at ambient temperature, and then 50 ml ethyl acetate and 10 ml water are added. The organic layer was separated, washed with aqueous NaHCO3 solution, and dried over MgSO4. After removal of the solvent, the residue was recrystallized from ethyl acetate and petrol ether.

Workup

  1. customThe organic layer was separated
  2. washwashed with aqueous NaHCO3 solution
  3. dry with materialdried over MgSO4
  4. customAfter removal of the solvent
  5. customthe residue was recrystallized from ethyl acetate and petrol ether

Sources & evidence

ORD record
ord-413a913df00642d2b3b65e2c77951fef
Source dataset
uspto-grants-2010_08
Patent number
US07772378B2

Reaction notes

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