Water → 2,5-Anhydro-4-S-[(4-methoxyphenyl)methyl]-4-thio-L-lyxose

HRID 54822Notes

Reaction equation

HRID 54822 reaction equation
C[O:2][CH:3](OC)[C@@H:4]1[O:19][CH2:18][C@H:7]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C@H:5]1[OH:6].FC(F)(F)C(O)=O.O>C(Cl)Cl>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][S:8][C@H:7]2[CH2:18][O:19][C@@H:4]([CH:3]=[O:2])[C@@H:5]2[OH:6])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 67648599HCID 67648599, compound

Product 1

HCID 883373162,5-Anhydro-4-S-[(4-methoxyphenyl)methyl]-4-thio-L-lyxoseYield 76.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of 0.340 g of product from Example 321 in 4 ml of methylene chloride is added a solution of 1 ml of trifluoroacetic acid and 0.266 ml of water. The reaction is stirred at room temperature for 1 hour, concentrated in vacuo, extracted with methylene chloride, neutralized with 1 g of sodium bicarbonate, filtered and concentrated in vacuo to give after chromatography (Silica gel: 50-60% ethyl acetate/hexane) 0.222 g of the desired product.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with methylene chloride
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d664a197188c4c6294bf510864d1ba56
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

Loading…