Water → HCID 12047164, compound

HRID 1009674Notes

Reaction equation

HRID 1009674 reaction equation
[CH2:1]([O:4][C@H:5]1[O:34][C@H:33]([CH2:35][OH:36])[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].[C:37]1([CH3:47])[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][CH:38]=1.O>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH2:1]([O:4][C@H:5]1[O:34][C@H:33]([CH2:35][O:36][S:43]([C:40]2[CH:41]=[CH:42][C:37]([CH3:47])=[CH:38][CH:39]=2)(=[O:45])=[O:44])[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:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 12041116Allyl 2,3,4-tri-O-benzyl-A-D-glucopyranoside

Product 1

HCID 12047164HCID 12047164, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of the compound (4) (25.1 g, 51.2 mmol) in anhydrous pyridine (250 ml) were added p-toluenesulfonyl chloride (14.6 g, 1.5 equivalents) and 4-dimethylaminopyridine (626 mg, 0.1 equivalents), and the reaction liquid was stirred at room temperature for 16 hours. After the sufficient progress of the reaction was confirmed, water (10 ml) was added to stop the reaction, and the reaction liquid was concentrated under reduced pressure. The residue was suspended in a minor amount of ethyl acetate, poured to 0.5 M hydrochloric acid (200 ml), and extracted with ethyl acetate (3×200 ml). The organic layers were combined, washed with a saturated sodium hydrogen carbonate solution (2×100 ml) and saturated saline (2×100 ml), dried with sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was crystallized twice from heated ethanol to obtain the title compound (5) in the form of colorless needle crystals (25.0 g). The filtrate was concentrated, purified with silica gel chromatography (hexane-ethyl acetate, 5:1→4:1→3:1) to obtain the compound (5) (4.00 g). {29.0 g (45.0 mmol) in total, 87.9%}.

Workup

  1. customthe reaction liquid
  2. customthe reaction
  3. customthe reaction liquid
  4. concentrationwas concentrated under reduced pressure
  5. additionpoured to 0.5 M hydrochloric acid (200 ml)
  6. extractionextracted with ethyl acetate (3×200 ml)
  7. washwashed with a saturated sodium hydrogen carbonate solution (2×100 ml) and saturated saline (2×100 ml)
  8. dry with materialdried with sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe obtained residue was crystallized twice
  12. temperaturefrom heated ethanol

Sources & evidence

ORD record
ord-0790153732df419695675b7f27f82665
Source dataset
uspto-grants-2011_07
Patent number
US07973145B2

Reaction notes

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