p-Toluenesulfonic acid monohydrate → HCID 70131219, compound

HRID 1769244Notes

Reaction equation

HRID 1769244 reaction equation
O.[C:2]1(C)C=CC(S(O)(=O)=O)=CC=1.[OH:13][CH2:14][C:15]1[C:16](=[O:23])[C@@H:17]2[O:22][CH2:21][C@H:19]([CH:20]=1)[O:18]2>CO>[CH3:2][O:13][CH2:14][C:15]1[C:16](=[O:23])[C@@H:17]2[O:22][CH2:21][C@H:19]([CH:20]=1)[O:18]2

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 70130686HCID 70130686, compound

Product 1

HCID 70131219HCID 70131219, compoundYield 44.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2 g of p-toluene sulfonic acid monohydrate was added to 150 ml of a methanol solution containing 2.8 g of 1,6-anhydro-3,4-dideoxy-3-hydroxymethyl-β-D-glycero-hex-3-enopyranos-2-ulose obtained in the above step (1), and the mixture was refluxed under heating for one hour. Disappearance of the starting material was confirmed by TLC, and then the solvent was distilled off under reduced pressure. The obtained crude product was purified by silica gel column chromatography (ethyl acetate: hexane =1:2) to obtain 0.8 g of the desired product (Intermediate No. 48). The NMR analytical data of this product are as follows.

Workup

  1. customobtained in the above step (1)
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating for one hour
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained crude product
  6. customwas purified by silica gel column chromatography (ethyl acetate: hexane =1:2)

Sources & evidence

ORD record
ord-7f77edf667ec403bac2b4178bc767826
Source dataset
uspto-grants-1995_01
Patent number
US05380834

Reaction notes

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