2α,3α-epoxy-1-mesyloxy-16-methoxy-8-(tert-butyldimethylsilyloxy)-8,9-secofusicocc-9-ene | 162132-85-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2α,3α-epoxy-1-mesyloxy-16-methoxy-8-(tert-butyldimethylsilyloxy)-8,9-secofusicocc-9-ene
• 英文别名: [(S)-[(1R,2S,5S)-2-[(2R)-1-[tert-butyl(dimethyl)silyl]oxypropan-2-yl]-5-(methoxymethyl)-6-oxabicyclo[3.1.0]hexan-1-yl]-[(1S,3R)-1-methyl-2-methylidene-3-propan-2-ylcyclopentyl]methyl] methanesulfonate
• CAS: 162132-85-6
• 化学式: C₂₈H₅₂O₆SSi
• 分子量: 544.869
• InChiKey: PRJRWISWFJCSAL-XFTCRZNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.18
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  82.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2α,3α-epoxy-1-mesyloxy-16-methoxy-8-(tert-butyldimethylsilyloxy)-8,9-secofusicocc-9-ene 在 吡啶 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 三氯化铁 、 calcium 、 sodium amide 作用下， 以 四氢呋喃 、 氨 、 水 为溶剂， 反应 22.0h， 生成 16-methoxy-3α-(trimethylsilyloxy)-8,9-secofusicocca-1,9-dien-8-ol
  参考文献：
  名称：

  Total synthesis of optically active cotylenol, a fungal metabolite having a leaf growth activity. Intramolecular ene reaction for an eight-membered ring formation

  摘要：

  Starting from condensation of two iridoid synthons, (3S,8R)-benzyloxy-1-iriden-7-al and (3R)-7-chloro-1-iridene, cotylenol, one of the representative fusicoccane diterpenoids having 5-8-5-membered tricyclic carbon framework, is now synthesized for the first time via an eight-membered ring formation by an intramolecular ene reaction and subsequent introduction of an alpha-hydroxyl group.

  DOI：

  10.1016/s0040-4020(96)00059-2
• 作为产物：
  描述：

  2α,3α-epoxy-16-methoxy-1-trimethylsilyloxy-8,9-secofusicocca-7,9-diene 在 吡啶 、 咪唑 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 四丁基氟化铵 、 双氧水 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.67h， 生成 2α,3α-epoxy-1-mesyloxy-16-methoxy-8-(tert-butyldimethylsilyloxy)-8,9-secofusicocc-9-ene
  参考文献：
  名称：

  Total synthesis of optically active cotylenol, a fungal metabolite having a leaf growth activity. Intramolecular ene reaction for an eight-membered ring formation

  摘要：

  Starting from condensation of two iridoid synthons, (3S,8R)-benzyloxy-1-iriden-7-al and (3R)-7-chloro-1-iridene, cotylenol, one of the representative fusicoccane diterpenoids having 5-8-5-membered tricyclic carbon framework, is now synthesized for the first time via an eight-membered ring formation by an intramolecular ene reaction and subsequent introduction of an alpha-hydroxyl group.

  DOI：

  10.1016/s0040-4020(96)00059-2

文献信息

• Total Synthesis of (−)-Cotylenol, a Fungal Metabolite Having a Leaf Growth Activity
  作者：Hiroaki Okamoto、Hiroaki Arita、Nobuo Kato、Hitoshi Takeshita

  DOI：10.1246/cl.1994.2335

  日期：1994.12

  Cotylenol, one of the representative fusicoccane diterpenoids having 5-8-5-membered tricyclic carbon framework, is now synthesized for the first time via an eight-membered ring formation by an intramolecular ene reaction followed by an oxidative formation of the 8β,9α-glycol function on the central eight-membered ring.

  Cotylenol 是一种具有 5-8-5 元三环碳骨架的代表性褐藻二萜类化合物，现在首次通过分子内烯反应形成八元环，然后氧化形成 8β,9α-中央八元环上的乙二醇功能。
• Total synthesis of optically active cotylenol, a fungal metabolite having a leaf growth activity. Intramolecular ene reaction for an eight-membered ring formation
  作者：Nobuo Kato、Hiroaki Okamoto、Hitoshi Takeshita

  DOI：10.1016/s0040-4020(96)00059-2

  日期：1996.3

  Starting from condensation of two iridoid synthons, (3S,8R)-benzyloxy-1-iriden-7-al and (3R)-7-chloro-1-iridene, cotylenol, one of the representative fusicoccane diterpenoids having 5-8-5-membered tricyclic carbon framework, is now synthesized for the first time via an eight-membered ring formation by an intramolecular ene reaction and subsequent introduction of an alpha-hydroxyl group.