HCID 15041765, compound → HCID 15041766, compound

HRID 1030779Notes

Reaction equation

HRID 1030779 reaction equation
C([O:4][CH2:5][C:6]1([CH2:28][O:29]C(=O)C)[O:15]C(OC(=O)C)[C@H:9]([O:16]C(=O)C)[C@@H:8]([O:20]C(=O)C)[C@H:7]1[O:24][C:25](=[O:27])C)(=O)C>C[O-].[Na+]>[OH:29][CH2:28][C:6]([CH2:5][OH:4])([OH:15])[C@@H:7]1[O:24][CH:25]([OH:27])[C@H:9]([OH:16])[C@H:8]1[OH:20]

Participants

3

Reactant 1

HCID 15041765HCID 15041765, compound

Product 1

HCID 15041766HCID 15041766, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

A solution of 5-C-(acetoxymethyl)-1,2,3,4,6-penta-O-acetyl-L-arabino-hexopyranose (7) (4.0 g, 8.7 mmol) in 0.05M methanolic sodium methoxide (50.0 ml) is stirred at room temperature for 2 hours. The reaction mixture is deionized with Amberlite IR-120 (H+) and evaporated to oily residue. Purification on a silica column with chloroform:methanol (4:1) followed by chloroform:methanol (3:2) gives 0.5 g (27%) of (8).

Workup

  1. customevaporated to oily residue
  2. customPurification on a silica column with chloroform:methanol (4:1)

Sources & evidence

ORD record
ord-dbf3c07a3a5f4998ab8cca77299871b5
Source dataset
uspto-grants-1992_04
Patent number
US05106967

Reaction notes

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