p-Toluenesulfonic acid → (5R,6R,6aR)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2,6a-trimethyl-tetrahydrofuro[3,2-d][1,3]dioxol-6-yl 4-methylbenzenesulfonate

HRID 409005Notes

Reaction equation

HRID 409005 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][C@H:12]2[C@:16]([OH:18])([CH3:17])[CH:15]([OH:19])[O:14][C@@H:13]2[CH2:20][O:21][Si:22]([C:35]([CH3:38])([CH3:37])[CH3:36])([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CO[C:41](OC)([CH3:43])[CH3:42].CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([O:11][C@H:12]2[C@@:16]3([CH3:17])[O:18][C:41]([CH3:43])([CH3:42])[O:19][CH:15]3[O:14][C@@H:13]2[CH2:20][O:21][Si:22]([C:35]([CH3:38])([CH3:37])[CH3:36])([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 516892Sodium BicarbonateHCID 86662594(2R,3R,4R)-2-((tert-butyldiphenylsilyloxy)methyl)-4,5-dihydroxy-4-methyl-tetrahydrofuran-3-yl 4-methylbenzenesulfonate

Product 1

HCID 86662593(5R,6R,6aR)-5-((tert-butyldiphenylsilyloxy)methyl)-2,2,6a-trimethyl-tetrahydrofuro[3,2-d][1,3]dioxol-6-yl 4-methylbenzenesulfonateYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of compounds (2R,3R,4R)-2-((tert-butyldiphenylsilyloxy)methyl)-4,5-dihydroxy-4-methyl-tetrahydrofuran-3-yl 4-methylbenzenesulfonate (from step 3) (58 g, 0.104 mol), 2,2-dimethoxy propane (25.7 mL, 0.209 mol) in 500 mL of anhydrous CH2Cl2 at 0° C., PTSA was added and stirred at room temperature for 2 h. The reaction mixture was poured into saturated NaHCO3 solution and organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. Purified by column chromatography using hexane and ethyl acetate as a gradient mixture to give 57.2 g of the title compound (92% yield).

Workup

  1. washwere washed with brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurified by column chromatography

Sources & evidence

ORD record
ord-9e7ecb778b9d446ab8c133d2fe037701
Source dataset
uspto-grants-2014_06
Patent number
US08759318B2

Reaction notes

Loading…