Hydrogen Peroxide → 1-O-(2,3,4-tri-O-benzyl-6-O-tosyl-alpha-D-glucopyranosyl)propane-1,3-diol

HRID 1009675Notes

Reaction equation

HRID 1009675 reaction equation
[CH2:1]([O:4][C@H:5]1[O:34][C@H:33]([CH2:35][O:36][S:37]([C:40]2[CH:46]=[CH:45][C:43]([CH3:44])=[CH:42][CH:41]=2)(=[O:39])=[O:38])[C@@H:24]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:6]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH:2]=[CH2:3].C12BC(CCC1)CCC2.[OH-:56].[Na+].OO>O1CCCC1.O>[CH2:8]([O:7][C@@H:6]1[C@@H:15]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@H:24]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:33]([CH2:35][O:36][S:37]([C:40]2[CH:46]=[CH:45][C:43]([CH3:44])=[CH:42][CH:41]=2)(=[O:39])=[O:38])[O:34][C@@H:5]1[O:4][CH2:1][CH2:2][CH2:3][OH:56])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 12047164HCID 12047164, compound

Product 1

HCID 578243751-O-(2,3,4-tri-O-benzyl-6-O-tosyl-alpha-D-glucopyranosyl)propane-1,3-diol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the compound (5) (29.0 g, 45.0 mmol) in anhydrous tetrahydrofuran (THF, 150 ml), added was a solution of 0.5 M 9-borabicyclo[3,3,1]nonane (9-BBN) in tetrahydrofuran (180 ml, 90.0 mmol) at 0° C. in an argon atmosphere. After a lapse of 1 hour, the reaction liquid was returned to room temperature, and continuously stirred for 10 hours. The reaction liquid was cooled again to 0° C., to which water (20 ml) was added firstly, and then 3 M sodium hydroxide solution (70 ml) and 35% hydrogen peroxide solution (70 ml) were added sequentially. After a lapse of 1 hour, the reaction liquid was returned to room temperature, and stirred for 12 hours. After the sufficient progress of the reaction was confirmed, the solution was extracted with ethyl acetate (3×100 ml), the organic layers were combined and washed with saturated saline (2×100 ml), dried with sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified with silica gel chromatography (hexane-ethyl acetate, 3:2→1:1→2:3) to obtain the title compound (6) in the form of a colorless oily substance {28.2 g (42.5 mmol), 94.4%}.

Workup

  1. customat 0° C.
  2. customAfter a lapse of 1 hour, the reaction liquid
  3. customwas returned to room temperature
  4. customThe reaction liquid
  5. additionwas added firstly
  6. customAfter a lapse of 1 hour, the reaction liquid
  7. customwas returned to room temperature
  8. stirringstirred for 12 hours
  9. extractionthe solution was extracted with ethyl acetate (3×100 ml)
  10. washwashed with saturated saline (2×100 ml)
  11. dry with materialdried with sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customThe obtained residue was purified with silica gel chromatography (hexane-ethyl acetate, 3:2→1:1→2:3)

Sources & evidence

ORD record
ord-c978b0dee7d24fe38b60c7828e109a04
Source dataset
uspto-grants-2011_07
Patent number
US07973145B2

Reaction notes

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