Trifluoromethanesulfonic anhydride → Methyl 2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-beta-D-glucopyranoside

HRID 742116Notes

Reaction equation

HRID 742116 reaction equation
[Si](O[CH2:19][C@H:20]1[O:27][C@@H:24]([O:25][CH3:26])[C@H:23]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:22]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@@H:21]1[O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C.[S:67]([O:74]S(C(F)(F)F)(=O)=O)([C:70]([F:73])([F:72])[F:71])(=[O:69])=[O:68].C([O-])(O)=O.[Na+]>ClCCl>[CH2:29]([O:28][C@@H:23]1[C@@H:22]([O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C@H:21]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C@@H:20]([CH2:19][O:74][S:67]([C:70]([F:73])([F:72])[F:71])(=[O:69])=[O:68])[O:27][C@H:24]1[O:25][CH3:26])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 67749Trifluoromethanesulfonic anhydrideHCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 516892Sodium BicarbonateHCID 11146901Methyl 6-O-tert-butyldiphenylsilyl-2,3,4-tri-O-benzyl-beta-D-glucopyranoside

Product 1

HCID 22842886Methyl 2,3,4-tri-O-benzyl-6-O-trifluoromethylsulfonyl-beta-D-glucopyranoside

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of methyl 6-O-tert-butyldiphenylsilyl-2,3,4-tri-O-benzyl-β-D-glucopyranoside (800 mg, 1.71 mmol) in 8.55 mL of dry dichloromethane at -78° C. was added 2,6-di-tert-butyl-4-methyl pyridine (632 mg, 3.08 mmol) followed by triflic anhydride (345 μl, 2.05 mmol). After stirring 15 minutes at -78° C., the mixture was warmed to room temperature over 20 minutes, and then poured into a solution of saturated aqueous NaHCO3 (20 mL) and extracted with ethyl acetate (50 mL). The organic layer was washed with saturated NaHCO3 (3×20 mL), saturated aqueous NaCl (1×20 mL), and dried over magnesium sulfate. Concentration provided crude target compound, which was used in the next step without further purification.

Workup

  1. temperaturethe mixture was warmed to room temperature over 20 minutes
  2. extractionextracted with ethyl acetate (50 mL)
  3. washThe organic layer was washed with saturated NaHCO3 (3×20 mL), saturated aqueous NaCl (1×20 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationConcentration
  6. customprovided crude target compound, which
  7. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-e79bc5b6e60040b6857f3057443c8117
Source dataset
uspto-grants-1996_09
Patent number
US05552534

Reaction notes

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