Water → (3R,3aS,6R,6aR)-6-Hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonate

HRID 2168165Notes

Reaction equation

HRID 2168165 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]1[O:16][C@@H:15]2[C@H:17]([OH:20])[CH2:18][O:19][C@@H:14]2[C@@H:13]1[OH:21].O>N1C=CC=CC=1>[CH3:11][C:1]1[CH:6]=[CH:5][C:4]([S:7]([O:21][C@@H:13]2[CH2:12][O:16][C@@H:15]3[C@H:17]([OH:20])[CH2:18][O:19][C@H:14]23)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 109756241,4:3,6-Dianhydro-D-mannitol

Product 1

HCID 13014014(3R,3aS,6R,6aR)-6-Hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-methylbenzenesulfonateYield 60%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

A solution of p-toluenesulfonyl chloride (24.8 g, 130 mmol) in pyridine (150 mL) was added to a stirred solution of isomannide (40) (19.0 g, 130 mmol) in pyridine (150 mL) over 1 hour at 0° C. then stirred at ambient temperature for 1 hour. The mixture was poured onto iced-water (1 L) then extracted with dichloromethane (3×300 mL). The organic phase washed with brine (300 mL), dried (MgSO4), filtered and reduced in vacuo to leave a residue. Flash chromatography over silica, eluting with ethyl acetate:heptane mixtures 0:100 to 50:50 gave monotosylate (50) (23.4 g, 60%) as a white solid.

Workup

  1. extractionthen extracted with dichloromethane (3×300 mL)
  2. washThe organic phase washed with brine (300 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customto leave a residue
  6. washFlash chromatography over silica, eluting with ethyl acetate

Sources & evidence

ORD record
ord-c2f90545e0704267a329965e84a3c625
Source dataset
uspto-grants-2015_06
Patent number
US09045492B2

Reaction notes

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