HCID 11322133, compound → HCID 86672613, compound

HRID 470708Notes

Reaction equation

HRID 470708 reaction equation
C[O-].[Na+].CO.C([O:9][C@@H:10]1[C@@H:16]([CH2:17][O:18]C(=O)C)[O:15][C@H:13]([CH3:14])[CH:12]=[CH:11]1)(=O)C>CO>[CH3:14][C@H:13]1[O:15][C@H:16]([CH2:17][OH:18])[C@@H:10]([OH:9])[CH:11]=[CH:12]1

Participants

4

Reactant 2

HCID 11322133HCID 11322133, compoundHCID 23694274Sodium methanolate methanol

Product 1

HCID 86672613HCID 86672613, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide/methanol solution (28% w/w, 0.40 ml, 2.1 mmol) was added to a methanol (15 ml) solution of 5,7-di-O-acetyl-2,6-anhydro-1,3,4-trideoxy-D-arabino-hept-3-enitol (Synlett, 1996, 185; and Tetrahedron: Asymm., 2003, 14, 757) (1.56 g, 6.83 mmol) and the resulting mixture was stirred at room temperature for 3 hours. DOWEX 50WX8-200 was added to the reaction mixture to adjust its pH to 4 and then insoluble matter was removed by filtration. The filtrate was concentrated under reduced pressure to give the title compound.

Workup

  1. additionwas added to the reaction mixture
  2. custominsoluble matter was removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-84db03beac5549399ee3f8909489ddb3
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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