(3aR,5R,6S,6aR)-2,2-dimethyl-5-[octa-2(Z),5(E)-dienyl]-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol | 550316-63-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,5R,6S,6aR)-2,2-dimethyl-5-[octa-2(Z),5(E)-dienyl]-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol
• 英文别名: (3aR,5R,6S,6aR)-2,2-dimethyl-5-[(2Z,5E)-octa-2,5-dienyl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 550316-63-7
• 化学式: C₁₅H₂₄O₄
• 分子量: 268.353
• InChiKey: MANYJYCDJVIFCH-GXIKWOBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,5R,6S,6aR)-2,2-dimethyl-5-[octa-2(Z),5(E)-dienyl]-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 在 吡啶 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 (2R,3R,4R)-4-hydroxy-5-methoxy-2-[octa-2(Z),5(E)-dienyl]tetrahydrofuran-3-yl benzoate
  参考文献：
  名称：

  Efficient syntheses of trans-(+)-laurediol from carbohydrate precursors

  摘要：

  Two routes for the synthesis of the marine natural product trans-laurediol 6 are described. In the first approach 6 is obtained in ten steps and 21% overall yield from monoacetone D-glucose. The second route provides the target in eleven steps and 13% yield from D-mannose. Both routes are more efficient, both in terms of number of steps and overall yield, than previously reported syntheses. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00078-8
• 作为产物：
  描述：

  5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-eno-furanose 在 palladium dichloride 氧气 、 双(三甲基硅烷基)氨基钾 、 copper(l) chloride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.0h， 生成 (3aR,5R,6S,6aR)-2,2-dimethyl-5-[octa-2(Z),5(E)-dienyl]-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol
  参考文献：
  名称：

  Efficient syntheses of trans-(+)-laurediol from carbohydrate precursors

  摘要：

  Two routes for the synthesis of the marine natural product trans-laurediol 6 are described. In the first approach 6 is obtained in ten steps and 21% overall yield from monoacetone D-glucose. The second route provides the target in eleven steps and 13% yield from D-mannose. Both routes are more efficient, both in terms of number of steps and overall yield, than previously reported syntheses. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00078-8

文献信息

• Efficient syntheses of trans-(+)-laurediol from carbohydrate precursors
  作者：Rajendrakumar Reddy Gadikota、Adam I. Keller、Christopher S. Callam、Todd L. Lowary

  DOI：10.1016/s0957-4166(03)00078-8

  日期：2003.3

  Two routes for the synthesis of the marine natural product trans-laurediol 6 are described. In the first approach 6 is obtained in ten steps and 21% overall yield from monoacetone D-glucose. The second route provides the target in eleven steps and 13% yield from D-mannose. Both routes are more efficient, both in terms of number of steps and overall yield, than previously reported syntheses. (C) 2003 Elsevier Science Ltd. All rights reserved.