Sodium Methoxide → 4-nitrophenyl 5-thio-beta-D-xylopyranoside

HRID 6035

Reaction equation

HRID 6035 reaction equation
C[O-].[Na+].C([O:7][C@@H:8]1[C@@H:23]([O:24]C(=O)C)[C@H:22]([O:28]C(=O)C)[CH2:21][S:20][C@H:9]1[O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1)(=O)C>CO>[O:10]([C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=1)[C@@H:9]1[S:20][CH2:21][C@@H:22]([OH:28])[C@H:23]([OH:24])[C@H:8]1[OH:7]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 150678484-nitrophenyl 2,3,4-tri-O-acetyl-5-thio-beta-D-xylopyranoside

Product 1

HCID 150678494-nitrophenyl 5-thio-beta-D-xylopyranosideYield 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

0.2 ml of a solution of sodium methylate in methanol (8% w/v of Na) is added under an inert atmosphere to a suspension of 1.1 g (2.6.10-3 mol) of 4-nitrophenyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranoside in 30 ml of methanol. After complete solubilization (2 h), the reaction mixture is neutralized by the addition of Amberlite® IR 120 H+ resin and then filtered. 620 mg (yield: 79%) of the expected product are obtained after evaporation to dryness and lyophilization.

Workup

  1. additionAfter complete solubilization (2 h), the reaction mixture is neutralized by the addition of Amberlite® IR 120 H+ resin
  2. filtrationfiltered

Sources & evidence

ORD record
ord-14c101d07d4f4ec98d6975cff8caa0ec
Source dataset
uspto-grants-1993_09
Patent number
US05246961

Linked notes

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