<3S-<3α(1R*,2R*,3S*,5R*,6E),4β(1E,3E)>>-1-<(1,1-dimethylethyl)dimethylsilyl>-4-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methyl-1,3-pentadienyl>-3-<3-<<(1,1-diphenylethyl)dimethylsilyl>oxy>-1-hydroxy-7-iodo-5-<(4-methoxyphenyl)methoxy>-2-methyl..>. | 152453-82-2

• 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: <3S-<3α(1R*,2R*,3S*,5R*,6E),4β(1E,3E)>>-1-<(1,1-dimethylethyl)dimethylsilyl>-4-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methyl-1,3-pentadienyl>-3-<3-<<(1,1-diphenylethyl)dimethylsilyl>oxy>-1-hydroxy-7-iodo-5-<(4-methoxyphenyl)methoxy>-2-methyl..>.
• 英文别名: (3S,4R)-1-[tert-butyl(dimethyl)silyl]-4-[(1E,3E)-5-[tert-butyl(dimethyl)silyl]oxy-2-methylpenta-1,3-dienyl]-3-[(E,1S,2S,3R,5S)-3-[tert-butyl(diphenyl)silyl]oxy-1-hydroxy-7-iodo-5-[(4-methoxyphenyl)methoxy]-2-methylhept-6-enyl]-3-methylazetidin-2-one
• CAS: 152453-82-2
• 化学式: C₅₄H₈₂INO₆Si₃
• 分子量: 1052.41
• InChiKey: FZQXDXDYAKCLGN-OQRMDBCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.61
• 重原子数：
  65
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  <3S-<3α(1R*,2R*,3S*,5R*,6E),4β(1E,3E)>>-1-<(1,1-dimethylethyl)dimethylsilyl>-4-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methyl-1,3-pentadienyl>-3-<3-<<(1,1-diphenylethyl)dimethylsilyl>oxy>-1-hydroxy-7-iodo-5-<(4-methoxyphenyl)methoxy>-2-methyl..>. 在 甲烷磺酸 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 <4R-<4α(2E,4E),4aβ,7α(2S*,3E),8β,8aβ>>-1H-imidazole-1-carboxylic acid 5--3-butenyl>-4a,8-dimethyl-2,5-dioxo-2H,5H-pyrano<3,4-e>-1,3-oxazin-4-yl>-4-methyl-2,4-pentadienyl ester
  参考文献：
  名称：

  Total Synthesis of the Macrolide Antitumor Antibiotic Lankacidin C

  摘要：

  The first total synthesis of natural (-)-lankacidin C (I) has been achieved by a convergent, enantioselective sequence starting from D-arabinose and L-aspartic acid, proceeding through the tricyclic carbamate 15 as an advanced relay intermediate. Specifically, the beta-lactam diene intermediate 41 is acylated by the thiopyridyl ester 34c. The resulting beta-ketolactam 42 is stereospecifically reduced by KEt(3)BH to carbinol 43, which on desilylation undergoes acid-catalyzed N --> O acyl migration to yield the delta-lactone 44. The derived iodo aldehyde 46 undergoes Stille coupling to give tetraene 54a, which upon Stork-Takahashi cyclization to ketone 56 and CBS reduction gives the key relay 15. N-acylation of the latter, and then regioselective carbamate scission followed by Dess-Martin oxidation, produces the target antibiotic (-)-lankacidin C (1).

  DOI：

  10.1021/ja00136a025
• 作为产物：
  描述：

  <2R-(2R*,3R*,5S*,6E)>-3-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-7-iodo-5-<(4-methoxyphenyl)methoxy>-2-methyl-6-heptenoic acid (S)-2-pyridinyl ester 在 三乙基氢硼化钾 、 lithium diisopropyl amide 作用下， 以 乙醚 为溶剂， 反应 0.67h， 生成 <3S-<3α(1R*,2R*,3S*,5R*,6E),4β(1E,3E)>>-1-<(1,1-dimethylethyl)dimethylsilyl>-4-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methyl-1,3-pentadienyl>-3-<3-<<(1,1-diphenylethyl)dimethylsilyl>oxy>-1-hydroxy-7-iodo-5-<(4-methoxyphenyl)methoxy>-2-methyl..>.
  参考文献：
  名称：

  Total Synthesis of the Macrolide Antitumor Antibiotic Lankacidin C

  摘要：

  The first total synthesis of natural (-)-lankacidin C (I) has been achieved by a convergent, enantioselective sequence starting from D-arabinose and L-aspartic acid, proceeding through the tricyclic carbamate 15 as an advanced relay intermediate. Specifically, the beta-lactam diene intermediate 41 is acylated by the thiopyridyl ester 34c. The resulting beta-ketolactam 42 is stereospecifically reduced by KEt(3)BH to carbinol 43, which on desilylation undergoes acid-catalyzed N --> O acyl migration to yield the delta-lactone 44. The derived iodo aldehyde 46 undergoes Stille coupling to give tetraene 54a, which upon Stork-Takahashi cyclization to ketone 56 and CBS reduction gives the key relay 15. N-acylation of the latter, and then regioselective carbamate scission followed by Dess-Martin oxidation, produces the target antibiotic (-)-lankacidin C (1).

  DOI：

  10.1021/ja00136a025