[(1S,2S,3R,4S,7R,9S,10S,11R,14S)-4,11-diacetyloxy-10-formyl-1,14-dihydroxy-9,13,16,16-tetramethyl-6-oxatetracyclo[10.3.1.03,10.04,7]hexadec-12-en-2-yl] benzoate | 154854-31-6

• 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,2S,3R,4S,7R,9S,10S,11R,14S)-4,11-diacetyloxy-10-formyl-1,14-dihydroxy-9,13,16,16-tetramethyl-6-oxatetracyclo[10.3.1.03,10.04,7]hexadec-12-en-2-yl] benzoate
• CAS: 154854-31-6
• 化学式: C₃₁H₃₈O₁₀
• 分子量: 570.637
• InChiKey: IHTDUKBDAJKLGS-AWOZUZKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  146
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(1S,2S,3R,4S,7R,9S,10S,11R,14S)-4,11-diacetyloxy-10-formyl-1,14-dihydroxy-9,13,16,16-tetramethyl-6-oxatetracyclo[10.3.1.03,10.04,7]hexadec-12-en-2-yl] benzoate 在 盐酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  Synthesis of Ring B-Rearranged Taxane Analogs

  摘要：

  Reaction of the C-7 hydroxyl group on the 9-dihydrotaxane skeleton with triflic anhydride causes a major skeletal rearrangement to occur leading to contraction of ring B. In addition the formation of a ring C-fused cyclopropane structure occurs. The requisite C-13 phenylisoserinate side chains are appended via an initial deacylation of the C-13 acetate followed by reacylation and deprotection. These rearranged compounds show very similar structural features with the parent 9-dihydrotaxane skeleton and also retain biological activity.

  DOI：

  10.1021/jo00088a017
• 作为产物：
  描述：

  13-乙酰基-9-羟基巴卡丁 III 在 三氟甲磺酸酐 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.17h， 生成 [(1S,2S,3R,4S,7R,9S,10S,11R,14S)-4,11-diacetyloxy-10-formyl-1,14-dihydroxy-9,13,16,16-tetramethyl-6-oxatetracyclo[10.3.1.03,10.04,7]hexadec-12-en-2-yl] benzoate
  参考文献：
  名称：

  Synthesis of Ring B-Rearranged Taxane Analogs

  摘要：

  Reaction of the C-7 hydroxyl group on the 9-dihydrotaxane skeleton with triflic anhydride causes a major skeletal rearrangement to occur leading to contraction of ring B. In addition the formation of a ring C-fused cyclopropane structure occurs. The requisite C-13 phenylisoserinate side chains are appended via an initial deacylation of the C-13 acetate followed by reacylation and deprotection. These rearranged compounds show very similar structural features with the parent 9-dihydrotaxane skeleton and also retain biological activity.

  DOI：

  10.1021/jo00088a017

文献信息

• Synthesis of Ring B-Rearranged Taxane Analogs
  作者：Larry L. Klein、Clarence J. Maring、Leping Li、Clinton M. Yeung、Sheela A. Thomas、David J. Grampovnik、J. J. Plattner、Rodger F. Henry

  DOI：10.1021/jo00088a017

  日期：1994.5

  Reaction of the C-7 hydroxyl group on the 9-dihydrotaxane skeleton with triflic anhydride causes a major skeletal rearrangement to occur leading to contraction of ring B. In addition the formation of a ring C-fused cyclopropane structure occurs. The requisite C-13 phenylisoserinate side chains are appended via an initial deacylation of the C-13 acetate followed by reacylation and deprotection. These rearranged compounds show very similar structural features with the parent 9-dihydrotaxane skeleton and also retain biological activity.