Water → 1-O-(2,3,4-tri-O-benzyl-6-thioacetyl-alpha-D-quinovopyranosyl)-propane-1,3-diol

HRID 1009676Notes

Reaction equation

HRID 1009676 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12](COS(C2C=CC(C)=CC=2)(=O)=O)[O:11][C@@H:10]1[O:43][CH2:44][CH2:45][CH2:46][OH:47])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:48]([O-])(=[S:50])[CH3:49].[K+].O.[CH3:54]N(C=O)C>>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@@H:12]([CH2:49][C:48](=[S:50])[CH3:54])[O:11][C@@H:10]1[O:43][CH2:44][CH2:45][CH2:46][OH:47])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 23670855Potassium ethanethioateHCID 578243751-O-(2,3,4-tri-O-benzyl-6-O-tosyl-alpha-D-glucopyranosyl)propane-1,3-diol

Product 1

HCID 866333751-O-(2,3,4-tri-O-benzyl-6-thioacetyl-alpha-D-quinovopyranosyl)-propane-1,3-diol

Conditions

Temperature
90 °C

Procedure

To a solution of the compound (6) (28.2 g, 42.5 mmol) in anhydrous DMF (300 ml), added was potassium thioacetate (7.28 g, 1.5 equivalents), and the mixture was stirred at 90° C. for 3 hours. After the sufficient progress of the reaction was confirmed, the reaction liquid was poured to chilled water (900 ml), extracted with ethyl acetate (3×300 ml). The organic layers were combined and washed with saturated saline (2×200 ml), dried with sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified with silica gel chromatography (hexane-ethyl acetate, 2:1→3:2→1:1→2:3) to obtain the title compound (7) in the form of light brown oily substance {21.9 g (38.6 mmol), 90.8%}.

Workup

  1. customthe reaction liquid
  2. additionwas poured
  3. extractionextracted with ethyl acetate (3×300 ml)
  4. washwashed with saturated saline (2×200 ml)
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained residue was purified with silica gel chromatography (hexane-ethyl acetate, 2:1→3:2→1:1→2:3)

Sources & evidence

ORD record
ord-6e8474a0a1584f3a8d1044a43dc015e4
Source dataset
uspto-grants-2011_07
Patent number
US07973145B2

Reaction notes

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