Sodium Methoxide → Benzyl alpha-D-lyxopyranoside

HRID 964864Notes

Reaction equation

HRID 964864 reaction equation
C([O:4][C@H:5]1[C@@H:18]([O:19]C(=O)C)[C@H:17]([O:23]C(=O)C)[CH2:16][O:15][C@@H:6]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)C.C[O-].[Na+]>CO.ClCCl.CO>[O:7]([CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C@H:6]1[O:15][CH2:16][C@@H:17]([OH:23])[C@H:18]([OH:19])[C@@H:5]1[OH:4]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 67638320Benzyl 2,3,4-tri-O-acetyl-alpha-D-lyxopyranoside

Product 1

HCID 11736583Benzyl alpha-D-lyxopyranosideYield 77.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A suspension of compound 3 (20 g) in dry methanol:dichloromethane (2:1, 400 ml) containing sodium methoxide in methanol (0.46 g. Na in 100 ml of methanol) was stirred at room temperature until starting product disappeared (tlc). The solution was then made neutral with mixed-bed resin (50 ml, BioRad AG501-X8), filtered and evaporated to dryness to give 4 (10.2 g, 76%).

Workup

  1. filtrationfiltered
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-bc3042cdd5234ae4ad54823f629d0a60
Source dataset
uspto-grants-1998_06
Patent number
US05773239

Reaction notes

Loading…