Acetic acid (2S,3S,4aS,5S,6R,8aS)-5-(tert-butyl-diphenyl-silanyloxy)-2,3-diphenyl-2,3,4a,5,6,8a-hexahydro-benzo[1,4]dioxin-6-yl ester | 849596-48-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2S,3S,4aS,5S,6R,8aS)-5-(tert-butyl-diphenyl-silanyloxy)-2,3-diphenyl-2,3,4a,5,6,8a-hexahydro-benzo[1,4]dioxin-6-yl ester
• 英文别名: [(2S,3S,4aS,5S,6R,8aS)-5-[tert-butyl(diphenyl)silyl]oxy-2,3-diphenyl-2,3,4a,5,6,8a-hexahydro-1,4-benzodioxin-6-yl] acetate
• CAS: 849596-48-1
• 化学式: C₃₈H₄₀O₅Si
• 分子量: 604.818
• InChiKey: BIQVMBUSFZKHRE-PQVJJDQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  44.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3S,4aS,5S,6R,8aS)-5-(tert-butyl-diphenyl-silanyloxy)-2,3-diphenyl-2,3,4a,5,6,8a-hexahydro-benzo[1,4]dioxin-6-yl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以2 mg的产率得到
  参考文献：
  名称：

  Synthesis of enantiopure cyclitols from (±)-3-bromocyclohexene mediated by intramolecular oxyselenenylation employing (S,S)-hydrobenzoin and (S)-mandelic acid as chiral sources

  摘要：

  Reaction of 3-bromocyclohexene with (SS)-hydrobenzoin and (S)-mandelic acid and subsequent intramolecular oxyselenenylation of the resulting allylic ethers followed by oxidation-elimination afforded the valuable cis-fused bicyclic olefins, (1S,3S,4S,6R)-3,4-diphenylbicyclo[4,4,0]-2,5-dioxa-7-decene and (1S,3S,4R)-3-phenyl-4a,7,8,8a-tetrahydro-benzo[1,4]dioxan-2-one, respectively. Further stereoselective transformation of these cis-fused bicyclic olefins afforded the enantiopure cyclohexitols, muco-quercitol, D-chiro-inocitol and allo-inocitol. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.003
• 作为产物：
  描述：

  (1S,3S,4S,6S,7S,8S,9S)-3,4-diphenyl-2,5-dioxa-7-tert-butyldiphenylsilyloxy-9-phenylselenobicyclo[4,4,0]decan-8-ol 在 吡啶 、 sodium periodate 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 50.0h， 生成 Acetic acid (2S,3S,4aS,5S,6R,8aS)-5-(tert-butyl-diphenyl-silanyloxy)-2,3-diphenyl-2,3,4a,5,6,8a-hexahydro-benzo[1,4]dioxin-6-yl ester
  参考文献：
  名称：

  Synthesis of enantiopure cyclitols from (±)-3-bromocyclohexene mediated by intramolecular oxyselenenylation employing (S,S)-hydrobenzoin and (S)-mandelic acid as chiral sources

  摘要：

  Reaction of 3-bromocyclohexene with (SS)-hydrobenzoin and (S)-mandelic acid and subsequent intramolecular oxyselenenylation of the resulting allylic ethers followed by oxidation-elimination afforded the valuable cis-fused bicyclic olefins, (1S,3S,4S,6R)-3,4-diphenylbicyclo[4,4,0]-2,5-dioxa-7-decene and (1S,3S,4R)-3-phenyl-4a,7,8,8a-tetrahydro-benzo[1,4]dioxan-2-one, respectively. Further stereoselective transformation of these cis-fused bicyclic olefins afforded the enantiopure cyclohexitols, muco-quercitol, D-chiro-inocitol and allo-inocitol. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.003