Trityl chloride → HCID 15432751, compound

HRID 610442Notes

Reaction equation

HRID 610442 reaction equation
[S:1]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[C:19]1([C:25](Cl)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>N1C=CC=CC=1>[C:19]1([C:25]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[O:12][CH2:11][C@H:9]2[O:10][C@@H:2]([S:1][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C@H:3]([OH:4])[C@@H:5]([OH:6])[C@@H:7]2[OH:8])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 10934592Phenyl 1-thio-beta-D-glucopyranoside

Product 1

HCID 15432751HCID 15432751, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Phenyl 1-thio-β-D-glucopyranoside (5) (7.01 g, 25.8 mmol) and triphenylmethyl chloride (9.33 g, 33.5 mmol) were suspended in pyridine (20 ml), and the mixture was refluxed for 5 hr. The solvent was evaporated under reduced pressure and the residue was dissolved in ethyl acetate. The resulting solution was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography (eluent; dichloromethane:ethyl acetate=1:1) to give phenyl 6-O-triphenylmethyl-1-thio-β-D-glucopyranoside (6) (13.1 g, yield 99%) as a white solid.

Workup

  1. temperaturethe mixture was refluxed for 5 hr
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe resulting solution was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue obtained
  8. customwas purified by silica gel column chromatography (eluent; dichloromethane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-f8e2623cfc7d4fa4af385e7739011aa4
Source dataset
uspto-grants-1999_12
Patent number
US05998595

Reaction notes

Loading…