Acetic Acid → HCID 86605975, compound

HRID 2246492Notes

Reaction equation

HRID 2246492 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 tetrabutylammonium fluoride in tetrahydrofuran are added to a solution of 1.3 g 1-methyl-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos1-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 is separated, washed with aqueous NaHCO3 solution, and dried over MgSO4. After removal of the solvent, the residue is recrystallized from a mixture of 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 a mixture of ethyl acetate and petrol ether

Sources & evidence

ORD record
ord-a9984e2510394ec4a4db492b24e04ccc
Source dataset
uspto-grants-2010_03
Patent number
US07687469B2

Reaction notes

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