tert-Butyl-dimethyl-[(2R,3R,4R,4aS,9aS)-4-(naphthalen-2-ylmethoxy)-2-(2-phenylsulfanyl-ethyl)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-silane | 917896-75-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyl-dimethyl-[(2R,3R,4R,4aS,9aS)-4-(naphthalen-2-ylmethoxy)-2-(2-phenylsulfanyl-ethyl)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-silane
• CAS: 917896-75-4
• 化学式: C₃₄H₄₄O₄SSi
• 分子量: 576.872
• InChiKey: KAQDPWXHMJPYOB-RGPGAZMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.41
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-Butyl-dimethyl-[(2R,3R,4R,4aS,9aS)-4-(naphthalen-2-ylmethoxy)-2-(2-phenylsulfanyl-ethyl)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-silane 在 N-氯代丁二酰亚胺 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 [(2R,3R,4R,4aS,9aS)-2-(2-chloro-2-phenylsulfanylethyl)-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-pyrano[3,2-b]oxepin-3-yl]oxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  Two Convergent Routes to the Left-Wing Fragment of Ciguatoxin CTX3C Using O,S-Acetals As Key Intermediates

  摘要：

  [GRAPHICS]Ciguatoxins, principal causative toxins of ciguatera seafood poisoning, are large ladderlike polycyclic ethers. Here, we report two convergent routes to synthesis of the multiolefinic left half of ciguatoxins based on a newly developed acyl radical strategy. Remarkably, only 13 steps from the monocyclic E-ring were required to construct the left wing.

  DOI：

  10.1021/ol062350h
• 作为产物：
  描述：

  [(2R,3R,4R,4aS,9aS)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-yl]-acetonitrile 在 吡啶 、 sodium tetrahydroborate 、 三丁基膦 、 二异丁基氢化铝 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.84h， 生成 tert-Butyl-dimethyl-[(2R,3R,4R,4aS,9aS)-4-(naphthalen-2-ylmethoxy)-2-(2-phenylsulfanyl-ethyl)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-3-yloxy]-silane
  参考文献：
  名称：

  Two Convergent Routes to the Left-Wing Fragment of Ciguatoxin CTX3C Using O,S-Acetals As Key Intermediates

  摘要：

  [GRAPHICS]Ciguatoxins, principal causative toxins of ciguatera seafood poisoning, are large ladderlike polycyclic ethers. Here, we report two convergent routes to synthesis of the multiolefinic left half of ciguatoxins based on a newly developed acyl radical strategy. Remarkably, only 13 steps from the monocyclic E-ring were required to construct the left wing.

  DOI：

  10.1021/ol062350h