Sulfuryl chloride → HCID 54049155, compound

HRID 363354Notes

Reaction equation

HRID 363354 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]1[O:17][C@H:14]([O:15][CH3:16])[C@H:13]([O:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@@H:12]([O:27][C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C@@H:11]1O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:40])(=O)=O>N1C=CC=CC=1>[CH2:1]([O:8][CH2:9][C@H:10]1[O:17][C@H:14]([O:15][CH3:16])[C@H:13]([O:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C@@H:12]([O:27][C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C@H:11]1[Cl:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 53779066HCID 53779066, compound2×

Product 1

HCID 54049155HCID 54049155, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of crude methyl 6-O-benzyl-2,3-di-O-benzoyl-α-D-glycopyranoside (compound 66) (from previous step) in 300 mL of pyridine at -40° C. was added sulfuryl chloride (15 mL). After 1 hour, the cooling bath was removed and stirring was continued at room temperature for 3 hours. Dichloromethane was then added and the resulting solution was washed with saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate and evaporated. The residue was chromatographed on a silica gel, eluting with dichloromethane, to provide methyl 6-O-benzyl-2,3-di-O-benzoyl-4-chloro-4-deoxy-α-D-galactopyranoside (compound 67) (15.3 g, 90.0% --based on compound 65) as a syrup.

Workup

  1. customthe cooling bath was removed
  2. waitwas continued at room temperature for 3 hours
  3. additionDichloromethane was then added
  4. washthe resulting solution was washed with saturated sodium bicarbonate solution and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on a silica gel
  8. washeluting with dichloromethane

Sources & evidence

ORD record
ord-0920e7ac9c7c4dc3b284081eb0b923a2
Source dataset
uspto-grants-1999_02
Patent number
US05874411

Reaction notes

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