p-Toluenesulfonic acid → 2,3:5,6-Di-O-isopropylidene-L-gulonolactone

HRID 329967

반응식

HRID 329967 반응식
[CH2:1]([OH:12])[C@H:2]([OH:11])[C@H:3]1[O:8][C:6](=[O:7])[C@@H:5]([OH:9])[C@H:4]1[OH:10].CO[C:15](OC)([CH3:17])[CH3:16].[C:20]1(C)[CH:25]=CC(S(O)(=O)=O)=C[CH:21]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.CC(C)=O.C(OCC)(=O)C>[CH3:16][C:15]1([CH3:17])[O:11][CH:2]([CH:3]2[O:8][C:6](=[O:7])[CH:5]3[O:9][C:20]([CH3:25])([CH3:21])[O:10][CH:4]23)[CH2:1][O:12]1

참가 물질

8

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 439373L-Gulonic acid, gamma-lactone2회HCID 516892Sodium Bicarbonate

생성물 1

HCID 5682882,3:5,6-Di-O-isopropylidene-L-gulonolactone수율 85%

시약·촉매·용매 3

HCID 180Acetone용매HCID 6212Chloroform용매HCID 8857Ethyl Acetate용매

실험 절차

m.p. 155° C. (from ethyl acetate) [α]D20 -76.6° (c, 1.99 in CHCl3), was prepared from L-gulonolactone in 85% yield as previously described by Fleet in copending application Ser. No. 249,153, filed Sept. 26, 1988. According to this method, the title compound is synthesized by treatment of L-gulonolactone with acetone and 2,2-dimethoxypropane and a catalytic amount of p-toluenesulfonic acid under dry nitrogen for 36 hours (h) followed by stirring with an excess of sodium bicarbonate, removing the solvent under reduced pressure, dissolving the residue in dichloromethane, washing with water, drying the organic extracts (MgSO4), removing the solvent under reduced pressure and recrystallizing from ethyl acetate to give a white crystalline solid.

후처리

  1. customremoving the solvent under reduced pressure
  2. dissolutiondissolving the residue in dichloromethane
  3. washwashing with water
  4. dry with materialdrying the organic extracts (MgSO4)
  5. customremoving the solvent under reduced pressure
  6. customrecrystallizing from ethyl acetate
  7. customto give a white crystalline solid

출처 및 근거

ORD 기록
ord-bdbb1b62a75e4e439207e4069eb2d41a
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04894388

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