Dichloromethane → HCID 131721316, compound

HRID 583166Notes

Reaction equation

HRID 583166 reaction equation
[CH2:1]([C:4]1([O:27][C@H:26]([CH2:28][O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@@H:24](O)[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)[OH:5])[CH:2]=[CH2:3].S(Cl)([Cl:40])(=O)=O.ClCCl>N1C=CC=CC=1>[CH2:1]([C:4]1([O:27][C@H:26]([CH2:28][O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:24]([Cl:40])[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)[OH:5])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24648Sulfuryl chlorideHCID 131721317HCID 131721317, compound

Product 1

HCID 131721316HCID 131721316, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Allyl-2,3,6-tri-O-benzyl-glucopyranose (as per Example 14) (960 mg) was dissolved in dry pyridine and added 65 μL of sulfuryl chloride at 0° C. dropwise. The reaction mixture was stirred at this temperature for 15 hours. Dichloromethane (150 mL) was added and the resulting solution was washed with sodium bicarbonate (2×150 mL) and water (2×150 mL). Solvent removal left the residue which was purified by chromatography on silica gel using hexane-ethyl acetate (5:1) as eluent to provide compound allyl 4-chloro-4-deoxy-2,3,6-tri-O-benzyl-galactopyranose (550 mg).

Workup

  1. washthe resulting solution was washed with sodium bicarbonate (2×150 mL) and water (2×150 mL)
  2. customSolvent removal
  3. waitleft the residue which
  4. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7a68188732304cbe8c2b303a30911008
Source dataset
uspto-grants-1999_07
Patent number
US05929037

Reaction notes

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