HCID 10626637, compound → HCID 10548421, compound

HRID 1757068Notes

Reaction equation

HRID 1757068 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]([CH:38]=[CH:39][CH:40]=1)[C:34]([O:36][CH3:37])=[O:35])(=O)C.C[O-].[Na+]>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]([CH:38]=[CH:39][CH:40]=2)[C:34]([O:36][CH3:37])=[O:35])[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

4

Reactant 2

HCID 10626637HCID 10626637, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 10548421HCID 10548421, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a dry 50 ml flask under nitrogen, methyl 3-(2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl)benzoate (2.18 g, 3.9 mmol) was dissolved in methanol (20 ml) and treated in one portion with sodium methoxide (250 mg) and the mixture was stirred at room temperature overnight, then concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 7:3 methylene chloride/methanol) which gave methyl 3-(2-(α-D-mannopyranosyloxy)phenyl)benzoate in 84% yield.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by flash chromatography (SiO2, 7:3 methylene chloride/methanol) which

Sources & evidence

ORD record
ord-1c8ed3386b8c457caf841f2dab046c1b
Source dataset
uspto-grants-1995_08
Patent number
US05444050

Reaction notes

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