[(3aS,4R,7aS)-6-(methoxymethoxymethyl)spiro[3a,4,5,7a-tetrahydro-1,3-benzodioxole-2,1'-cyclohexane]-4-yl]oxy-tert-butyl-dimethylsilane | 221097-98-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3aS,4R,7aS)-6-(methoxymethoxymethyl)spiro[3a,4,5,7a-tetrahydro-1,3-benzodioxole-2,1'-cyclohexane]-4-yl]oxy-tert-butyl-dimethylsilane
• CAS: 221097-98-9
• 化学式: C₂₁H₃₈O₅Si
• 分子量: 398.615
• InChiKey: YBZVTPAPYPIYBL-OTWHNJEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(3aS,4R,7aS)-6-(methoxymethoxymethyl)spiro[3a,4,5,7a-tetrahydro-1,3-benzodioxole-2,1'-cyclohexane]-4-yl]oxy-tert-butyl-dimethylsilane 在 四丁基氟化铵 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 为溶剂， 生成 (3aS,7aS)-6-(methoxymethoxymethyl)spiro[5,7a-dihydro-3aH-1,3-benzodioxole-2,1'-cyclohexane]-4-one
  参考文献：
  名称：

  Studies toward the construction of the allyltrisulfide component in esperamicin-A1 from 5-ketoshikimic acid derivatives: Part 2

  摘要：

  The MOM protected keto alcohol 7 was successfully converted to the silyl enol ether 4 by reaction with BSA. Reaction of this intermediate with dioxirane led to formation of allylic alcohol 10. Lactone 15 was obtained by reaction of tosylate 14 with the cuprate reagent derived from ethyl bromoacetate. Through a short sequence of reactions this 5-membered lactone was isomerized to the target lactone product 18. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02400-9
• 作为产物：
  描述：

  methyl (3S,4S,5R)-5-O-tert-butyldimethylsilyl-3,4-O-cyclohexylidene-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate 在 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 [(3aS,4R,7aS)-6-(methoxymethoxymethyl)spiro[3a,4,5,7a-tetrahydro-1,3-benzodioxole-2,1'-cyclohexane]-4-yl]oxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  Studies toward the construction of the allyltrisulfide component in esperamicin-A1 from 5-ketoshikimic acid derivatives: Part 2

  摘要：

  The MOM protected keto alcohol 7 was successfully converted to the silyl enol ether 4 by reaction with BSA. Reaction of this intermediate with dioxirane led to formation of allylic alcohol 10. Lactone 15 was obtained by reaction of tosylate 14 with the cuprate reagent derived from ethyl bromoacetate. Through a short sequence of reactions this 5-membered lactone was isomerized to the target lactone product 18. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02400-9

文献信息

• Studies toward the construction of the allyltrisulfide component in esperamicin-A1 from 5-ketoshikimic acid derivatives: Part 2
  作者：Sandrine Piguel、Gerardo Ulibarri、David S. Grierson

  DOI：10.1016/s0040-4039(98)02400-9

  日期：1999.1

  The MOM protected keto alcohol 7 was successfully converted to the silyl enol ether 4 by reaction with BSA. Reaction of this intermediate with dioxirane led to formation of allylic alcohol 10. Lactone 15 was obtained by reaction of tosylate 14 with the cuprate reagent derived from ethyl bromoacetate. Through a short sequence of reactions this 5-membered lactone was isomerized to the target lactone product 18. (C) 1998 Elsevier Science Ltd. All rights reserved.