Tetrahydrofuran → HCID 53884145, compound

HRID 2372813Notes

Reaction equation

HRID 2372813 reaction equation
C[O-].[Na+].C([O:7][C@@H:8]1[C@@H:29]([O:30]C(=O)C)[C@H:28]([O:34]C(=O)C)[CH2:27][S:26][C@H:9]1[S:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1)(=O)C.O1CCCC1>CO.C(O)C.O>[S:10]([C:11]1[CH:12]=[CH:13][C:14]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[CH:15][CH:16]=1)[C@@H:9]1[S:26][CH2:27][C@@H:28]([OH:34])[C@H:29]([OH:30])[C@H:8]1[OH:7]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 10942334Sodium MethoxideHCID 54459120HCID 54459120, compound

Product 1

HCID 53884145HCID 53884145, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 19096565Water ethanolSolvent

Procedure

A solution of 0.35 cm3 of sodium methylate in methanol (3.5 molar) is added to a suspension of 6.5 g of 4-(phenylsulfonyl)phenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside in 150 ml of methanol. The mixture obtained is stirred at room temperature for 1.5 h under nitrogen and 250 cm3 of tetrahydrofuran are then added. A clear solution is obtained, after which Amberlite® IR 120 H+ resin is added to pH 6. The mixture is filtered and the solvents are evaporated off under reduced pressure. After recrystallization from a methanol/water mixture (50/50 v/v), followed by dissolution in an ethanol/water mixture (50/50 v/v) and lyophilization, 3.3 g of the expected product (yield: 67%) are obtained.

Workup

  1. customThe mixture obtained
  2. customA clear solution is obtained
  3. additionafter which Amberlite® IR 120 H+ resin is added to pH 6
  4. filtrationThe mixture is filtered
  5. customthe solvents are evaporated off under reduced pressure
  6. customAfter recrystallization from a methanol/water mixture (50/50 v/v)

Sources & evidence

ORD record
ord-57fee21d6186401286dedd006715d6c5
Source dataset
uspto-grants-1992_03
Patent number
US05100913

Reaction notes

Loading…