(4aS,8R,8aS)-7-Benzenesulfonyl-8-benzyloxy-4a,5,8,8a-tetrahydro-4H-benzo[1,3]dioxine | 139277-14-8

• 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: (4aS,8R,8aS)-7-Benzenesulfonyl-8-benzyloxy-4a,5,8,8a-tetrahydro-4H-benzo[1,3]dioxine
• CAS: 139277-14-8
• 化学式: C₂₁H₂₂O₅S
• 分子量: 386.469
• InChiKey: OKMMIINFGIYFDQ-YYWHXJBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4aS,8R,8aS)-7-Benzenesulfonyl-8-benzyloxy-4a,5,8,8a-tetrahydro-4H-benzo[1,3]dioxine 在 甲醇 、 disodium hydrogenphosphate 、 sodium amalgam 作用下， 反应 4.0h， 以75%的产率得到(4aR,8R,8aR)-8-Benzyloxy-4a,5,8,8a-tetrahydro-4H-benzo[1,3]dioxine
  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
• 作为产物：
  描述：

  7-oxabicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid 在 氢氧化钾 、 lithium aluminium tetrahydride 、 正丁基锂 、 四甲基乙二胺 、 对甲苯磺酸 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 88.25h， 生成 (4aS,8R,8aS)-7-Benzenesulfonyl-8-benzyloxy-4a,5,8,8a-tetrahydro-4H-benzo[1,3]dioxine
  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

文献信息

• 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
  作者：Jose Luis Acena、Odon Arjona、Roberto Fernandez de la Pradilla、Joaquin Plumet、Alma Viso

  DOI：10.1021/jo00100a052

  日期：1994.10

  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.