(1S,2R,6S)-3-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-3-enol | 139277-12-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R,6S)-3-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-3-enol
• 英文别名: (1S,2R,6S)-3-(benzenesulfonyl)-2-[tert-butyl(dimethyl)silyl]oxy-6-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclohex-3-en-1-ol
• CAS: 139277-12-6
• 化学式: C₂₅H₄₄O₅SSi₂
• 分子量: 512.858
• InChiKey: SWYBGPGPOUGVKR-VJBMBRPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.14
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  81.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R,6S)-3-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-3-enol 在 叔丁基过氧化氢 、 正丁基锂 、 二叔丁基过氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 生成 D,L-(1,2,3,5/4)-1,2-Anhydro-3,4-bis-O-(tert-butyldimethylsilyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2-C-(phenylsulfonyl)-1,2,3,4-cyclohexanetetrol
  参考文献：
  名称：

  A Stereodivergent Access to Naturally Occurring Aminocarba Sugars from (Phenylsulfonyl)-7-oxabicyclo[2.2.1]heptane Derivatives. Total Synthesis of Penta-N,O-Acetyl-(.+-.)-Validamine and Its C1 and C2 Stereoisomers

  摘要：

  The total syntheses of the antibiotic component validamine 1 and its three diastereomers 2-4 have been accomplished as their racemic penta-N,O-acetates via stereocontrolled nucleophilic epoxidation of polyhydroxylated cyclohexenyl sulfones, obtained from (phenylsulfonyl)-7-oxabicyclo[2.2.1]heptanes. The diastereoselectivity of the epoxidation can be readily controlled by careful choice of the hydroxyl protecting groups. Ring opening of the resulting alpha,beta-epoxy sulfones followed by stereocontrolled introduction of an amine precursor led to the four C-1 and C-2 diastereomers of 1-aminocarbasugars.

  DOI：

  10.1021/jo00100a052
• 作为产物：
  描述：

  7-oxabicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid 在 咪唑 、 lithium aluminium tetrahydride 、 正丁基锂 、 四甲基乙二胺 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 99.0h， 生成 (1S,2R,6S)-3-Benzenesulfonyl-2-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-3-enol
  参考文献：
  名称：

  Strain-directed bridge cleavage of (phenylsulfonyl)-7-oxabicyclo[2.2.1]heptane derivatives: application to the total synthesis of carba-.alpha.-DL-glucopyranose

  摘要：

  New methodology to prepare highly oxygenated cyclohexenylsulfones by regioselective beta-elimination of (phenylsulfonyl)-7-oxabicyclo[2.2.1]heptane derivatives has been developed, and its application to the total synthesis of carba-alpha-DL-glucopyranose is described.

  DOI：

  10.1021/jo00033a002