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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
ノート
印刷プレビュー

反応式

HRID 409005 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 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
収率 92.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-9e7ecb778b9d446ab8c133d2fe037701
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08759318B2

反応ノート

読み込み中…

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