[(1S,3S,3'S,4S)-1-hydroxy-4,6,6-trimethylspiro[2,5-dioxabicyclo[2.2.2]octane-3,6'-oxane]-3'-yl]methyl 4-methylbenzenesulfonate | 226927-03-3

• 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,3S,3'S,4S)-1-hydroxy-4,6,6-trimethylspiro[2,5-dioxabicyclo[2.2.2]octane-3,6'-oxane]-3'-yl]methyl 4-methylbenzenesulfonate
• CAS: 226927-03-3
• 化学式: C₂₁H₃₀O₇S
• 分子量: 426.531
• InChiKey: UEPAEAOUWYJYQU-FIRPJDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  99.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲醇 、 [(1S,3S,3'S,4S)-1-hydroxy-4,6,6-trimethylspiro[2,5-dioxabicyclo[2.2.2]octane-3,6'-oxane]-3'-yl]methyl 4-methylbenzenesulfonate 在 对甲苯磺酸 、 sodium iodide 作用下， 生成 (1S,3S,4S,5'S)-5'-(iodomethyl)-1-methoxy-4,6,6-trimethylspiro[2,5-dioxabicyclo[2.2.2]octane-3,2'-oxane]
  参考文献：
  名称：

  Studies on the total synthesis of the saponaceolides. 1. Enantioselective synthesis of the spiroketal subunit

  摘要：

  An asymmetric synthesis of the tricyclic spiroketal subunit of the saponaceolides is described in which the absolute stereochemistry at C-2' and C-6' is established through a conformationally and stereoelectronically controlled cyclization of a dihydroxyketone pyran Intermediate. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00366-4
• 作为产物：
  描述：

  (4R)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-1-[(2S,5S)-5-hydroxy-2,6,6-trimethyloxan-2-yl]pentane-1,5-diol 在 吡啶 、 盐酸 、 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 7.0h， 生成 [(1S,3S,3'S,4S)-1-hydroxy-4,6,6-trimethylspiro[2,5-dioxabicyclo[2.2.2]octane-3,6'-oxane]-3'-yl]methyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Studies on the total synthesis of the saponaceolides. 1. Enantioselective synthesis of the spiroketal subunit

  摘要：

  An asymmetric synthesis of the tricyclic spiroketal subunit of the saponaceolides is described in which the absolute stereochemistry at C-2' and C-6' is established through a conformationally and stereoelectronically controlled cyclization of a dihydroxyketone pyran Intermediate. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00366-4

文献信息

• Studies on the total synthesis of the saponaceolides. 1. Enantioselective synthesis of the spiroketal subunit
  作者：Giovanni Vidari、Gianluigi Lanfranchi、Natalina Pazzi、Stefano Serra

  DOI：10.1016/s0040-4039(99)00366-4

  日期：1999.4

  An asymmetric synthesis of the tricyclic spiroketal subunit of the saponaceolides is described in which the absolute stereochemistry at C-2' and C-6' is established through a conformationally and stereoelectronically controlled cyclization of a dihydroxyketone pyran Intermediate. (C) 1999 Elsevier Science Ltd. All rights reserved.