Sodium Methoxide → HCID 131719637, compound

HRID 2395229Notes

Reaction equation

HRID 2395229 reaction equation
[CH2:1]1[C@:6](O)([CH2:7][OH:8])[C@@H:5]([OH:10])[C@H:4]([OH:11])[C@@H:3]([OH:12])[C@H:2]1[NH2:13].O=[CH:15][C@@H:16]([C@H:18]([C@@H:20]([C@@H:22]([CH2:24][OH:25])[OH:23])[OH:21])[OH:19])[OH:17].C[O-].[Na+]>CO>[CH:1]1[C@H:2]([NH2:13])[C@H:3]([OH:12])[C@@H:4]([OH:11])[C@H:5]([OH:10])[C:6]=1[CH2:7][OH:8].[CH2:24]1[O:25][C@@H:15]2[O:23][C@H:22]1[C@@H:20]([OH:21])[C@H:18]([OH:19])[C@H:16]2[OH:17]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 131719636HCID 131719636, compound2×

Product 1

HCID 131719637HCID 131719637, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

482 mg (0.843 mmol) of 1,6-anhydro-3,4-di-O-acetyl-2-deoxy-2-[1D-(1N,2,4/3)-(2,3,4-tri-O-acetyl-5-C-acetoxymethyl-2,3,4-trihydroxy-5-cyclohexen-1-yl)amino]-β-D-glucopyranose (compound 4) was dissolved in dry methanol (20 ml) and a methanolic solution of sodium methoxide (0.5N, 0.1 ml) was added. After 4 hours, solvent was evaporated and the residue was purified by passing through a column of sephadex using water:ethanol (1:1) as eluent to provide pure 1,6-anhydro-2-deoxy-2-[1D-(1N,2,4/3)-5-C-hydroxymethyl-2,3,4-trihydroxy-5-cyclohexen-1-yl)amino]-β-D-glucopyranose (compound 5) (249 mg, 92.5%) as white powder after lyophilization.

Workup

  1. customsolvent was evaporated
  2. customthe residue was purified

Sources & evidence

ORD record
ord-0a7c81af3ab44a0d907e8e9a0ae1e049
Source dataset
uspto-grants-1998_09
Patent number
US05814616

Reaction notes

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