Water → HCID 67078662, compound

HRID 1626012Notes

Reaction equation

HRID 1626012 reaction equation
S(Cl)([Cl:4])(=O)=O.[C:6]([O:14][C@H:15]1[C@H:20](O)[C@@H:19]([CH2:22][O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:18][CH2:17][CH2:16]1)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O>N1C=CC=CC=1>[C:6]([O:14][C@@H:15]1[CH2:16][CH2:17][O:18][C@H:19]([CH2:22][O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:20]1[Cl:4])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 11002380HCID 11002380, compound

Product 1

HCID 67078662HCID 67078662, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Sulfonyl chloride (29 μl) was added to a solution of 1,5-anhydro-3-O-benzoyl-6-O-benzyl-2-deoxy-D-arabino-hexitol obtained by the method described in J. Org. Chem. 67. 3346-3354 (2002) (94 mg) in pyridine (27 mg) under ice-cooling, and the mixture was stirred at room temperature for 4 hours. Water was added, followed by extraction with ethyl acetate. Then, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane) to give the title compound (27 mg).

Workup

  1. customobtained by the method
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThen, the organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane)

Sources & evidence

ORD record
ord-e96849a97494431091e6b290159cb79f
Source dataset
uspto-grants-2014_07
Patent number
US08785438B2

Reaction notes

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