Sodium Methoxide → HCID 11138003, compound

HRID 1372832Notes

Reaction equation

HRID 1372832 reaction equation
C[O-].[Na+].C([O:12][CH2:13][C@:14]1([O:48][CH2:47][C@@H:37]([O:38]C(=O)C2C=CC=CC=2)[C@@H:27]([O:28]C(=O)C2C=CC=CC=2)[C@@H:17]1[O:18]C(=O)C1C=CC=CC=1)[O:15][CH3:16])(=O)C1C=CC=CC=1>CO>[CH3:16][O:15][C@@:14]1([O:48][CH2:47][C@@H:37]([OH:38])[C@@H:27]([OH:28])[C@@H:17]1[OH:18])[CH2:13][OH:12]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 69460375HCID 69460375, compound

Product 1

HCID 11138003HCID 11138003, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of sodium methoxide (0.5 M in methanol, 10.0 ml) was added to a vigorously stirred solution of 1,3,4,5-tetra-O-benzoyl-2-O-methyl-β-D-fructopyranose (10.0 g, 16.4 mmol) in anhydrous methanol. After stirring for 1.5 hrs at room temperature the reaction was complete. The pH was adjusted to 7.0 with Amberlite IRC-50 (˜4.0 g). The solids were removed by filtration and the filtrate was concentrated in vacuo. Purification on a silica gel column (methanol:dichloromethane, 4:1 and 3:1) provided the product as white foam 2.70 g (81%).

Workup

  1. customThe solids were removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customPurification on a silica gel column (methanol:dichloromethane, 4:1 and 3:1)

Sources & evidence

ORD record
ord-0f259b33f3384440a8112b8246ee8c7a
Source dataset
uspto-grants-2007_01
Patent number
US07160867B2

Reaction notes

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