[4-[2-[2-[(2R,4R)-2,4-bis[[tert-butyl(dimethyl)silyl]oxy]heptadecyl]-1,3-dithian-2-yl]ethyl]phenoxy]-tert-butyl-dimethylsilane | 1226954-59-1

• 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: [4-[2-[2-[(2R,4R)-2,4-bis[[tert-butyl(dimethyl)silyl]oxy]heptadecyl]-1,3-dithian-2-yl]ethyl]phenoxy]-tert-butyl-dimethylsilane
• CAS: 1226954-59-1
• 化学式: C₄₇H₉₂O₃S₂Si₃
• 分子量: 853.634
• InChiKey: APYSRUKEIAFLGY-OCQXTOTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.83
• 重原子数：
  55
• 可旋转键数：
  28
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  78.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [4-[2-[2-[(2R,4R)-2,4-bis[[tert-butyl(dimethyl)silyl]oxy]heptadecyl]-1,3-dithian-2-yl]ethyl]phenoxy]-tert-butyl-dimethylsilane 在 对甲苯磺酸 、 phenyliodonium(III) bis(trifloroacetate) 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 0.08h， 生成 aculeatin A 、 (2R,4R,6R)-4-hydroxy-2-tridecyl-1,7-dioxadispiro[5.1.5.2]pentadeca-9,12-dien-11-one
  参考文献：
  名称：

  Stereoselective synthesis of bioactive natural spiroacetals aculeatins A and B

  摘要：

  The stereoselective synthesis of two naturally occurring bioactive spiroacetals, aculeatins A and B has been accomplished using 1-tetradecanal as the starting material. The sequence introduces diastereoselective iodine-induced electrophilic cyclization and ring opening of epoxide with 1,3-dithiane as the key steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.162
• 作为产物：
  描述：

  tert-butyl-[(2R,4R)-2-[tert-butyl(dimethyl)silyl]oxy-1-(1,3-dithian-2-yl)heptadecan-4-yl]oxy-dimethylsilane 、 2-(4’-t-butyldimethylsilyloxyphenyl)-1-iodoethane 在 正丁基锂 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 以84%的产率得到[4-[2-[2-[(2R,4R)-2,4-bis[[tert-butyl(dimethyl)silyl]oxy]heptadecyl]-1,3-dithian-2-yl]ethyl]phenoxy]-tert-butyl-dimethylsilane
  参考文献：
  名称：

  Stereoselective synthesis of bioactive natural spiroacetals aculeatins A and B

  摘要：

  The stereoselective synthesis of two naturally occurring bioactive spiroacetals, aculeatins A and B has been accomplished using 1-tetradecanal as the starting material. The sequence introduces diastereoselective iodine-induced electrophilic cyclization and ring opening of epoxide with 1,3-dithiane as the key steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.162

文献信息

• Stereoselective synthesis of bioactive natural spiroacetals aculeatins A and B
  作者：Biswanath Das、Martha Krishnaiah、Chithaluri Sudhakar

  DOI：10.1016/j.bmcl.2010.01.162

  日期：2010.4

  The stereoselective synthesis of two naturally occurring bioactive spiroacetals, aculeatins A and B has been accomplished using 1-tetradecanal as the starting material. The sequence introduces diastereoselective iodine-induced electrophilic cyclization and ring opening of epoxide with 1,3-dithiane as the key steps. (C) 2010 Elsevier Ltd. All rights reserved.