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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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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 409005
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HRID 409005 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

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반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-9e7ecb778b9d446ab8c133d2fe037701
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08759318B2

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