Acetic Acid → HCID 86605975, compound

HRID 2263592Notes

Reaction equation

HRID 2263592 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 mm at ambient temperature, and then 50 ml ethyl acetate and 10 ml water are added. The organic layer is separated, washed with aqueous NaHCO3 solution, and dried over MgSO4. After removal of the solvent, the residue is recrystallized from ethyl acetate and petrol ether.

Workup

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

Sources & evidence

ORD record
ord-16f2d90edf76449ba40322aa3bb01634
Source dataset
uspto-grants-2010_12
Patent number
US07851602B2

Reaction notes

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