<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 | 152453-80-0

• 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: <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
• 英文别名: S-pyridin-2-yl (E,2R,3R,5S)-3-[tert-butyl(diphenyl)silyl]oxy-7-iodo-5-[(4-methoxyphenyl)methoxy]-2-methylhept-6-enethioate
• CAS: 152453-80-0
• 化学式: C₃₇H₄₂INO₄SSi
• 分子量: 751.801
• InChiKey: XBGKHFPQVFEIDP-PDTLVYFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.21
• 重原子数：
  45
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  83
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  4-甲氧基溴苄 在 咪唑 、 chromium dichloride 、 lead(IV) acetate 、 lithium hydroxide 、 sodium hydroxide 、 sodium chlorite 、 sodium dihydrogenphosphate 、 二甲基硫 、 oil scarlet 、 三氟化硼乙醚 、 双氧水 、 氧气 、 sodium hydride 、 臭氧 、 三苯基膦 、 calcium carbonate 、 mercury dichloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 86.0h， 生成 <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
  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