Chloroform → HCID 10835056, compound

HRID 1757071Notes

Reaction equation

HRID 1757071 reaction equation
C([O:4][C@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@@H:6]1[O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31]1[CH:32]=[C:33]([CH2:37][C:38]([O:40][CH3:41])=[O:39])[CH:34]=[CH:35][CH:36]=1)(=O)C.C[O-].[Na+].C(Cl)(Cl)Cl>CO>[C@H:6]1([O:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]2[CH:32]=[C:33]([CH2:37][C:38]([O:40][CH3:41])=[O:39])[CH:34]=[CH:35][CH:36]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@@H:5]1[OH:4]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 10507309HCID 10507309, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 10835056HCID 10835056, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Methyl 3-(2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl)phenylacetate (3.96 g, 6.9 mmol, from Part E, EXAMPLE 2) was dissolved in methanol (50 ml), sodium methoxide (100 mg) was added and the solution stirred at room temperature for two hours. The reaction mixture was neutralized with Dowex-50W ion exchange resin (H+ form), filtered and concentrated in vacuo. Chromatography (silica, 9:1 CHCl3 :methanol) gave methyl 3-(2-(α-D-mannopyranosyloxy)phenyl)phenylacetate (2.8 g, quantitative yield (~100%)).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-170b4b3f95014d0697532cf22a87c32f
Source dataset
uspto-grants-1995_08
Patent number
US05444050

Reaction notes

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