<4R-<4R*>>-<<1-<2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-<(4-methoxyphenyl)methoxy>ethyl>-2-methyl-3-butenyl>oxy>(1,1-dimethylethyl)diphenylsilane | 152453-74-2

• 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: <4R-<4R*>>-<<1-<2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-<(4-methoxyphenyl)methoxy>ethyl>-2-methyl-3-butenyl>oxy>(1,1-dimethylethyl)diphenylsilane
• 英文别名: tert-butyl-[(1S,3R,4S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-[(4-methoxyphenyl)methoxy]-4-methylhex-5-en-3-yl]oxy-diphenylsilane
• CAS: 152453-74-2
• 化学式: C₃₆H₄₈O₅Si
• 分子量: 588.86
• InChiKey: KTFFTYQSSXPFKA-BJHVCKBZSA-N

物化性质

• 沸点：
  622.3±55.0 °C(predicted)
• 密度：
  1.07±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.89
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  <4R-<4R*>>-<<1-<2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-<(4-methoxyphenyl)methoxy>ethyl>-2-methyl-3-butenyl>oxy>(1,1-dimethylethyl)diphenylsilane 在 双(乙腈)氯化钯(II) 咪唑 、 2,6-二甲基吡啶 、 chromium dichloride 、 lead(IV) acetate 、 盐酸 、 potassium cyanide 、 lithium hydroxide 、 sodium hydroxide 、 sodium chlorite 、 sodium dihydrogenphosphate 、 硼烷四氢呋喃络合物 、 ammonium cerium(IV) nitrate 、 甲烷磺酸 、 18-冠醚-6 、 二甲基硫 、 oil scarlet 、 四丁基氟化铵 、 氧气 、 三乙基氢硼化钾 、 戴斯-马丁氧化剂 、 臭氧 、 溶剂黄146 、 甲基磺酰氯 、 三乙胺 、 三苯基膦 、 lithium chloride 、 lithium hexamethyldisilazane 、 lithium diisopropyl amide 、 (R)-CBS 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 68.0h， 生成 <1S,4(2S),5R,6E,8E,10S,12E,14E,16S,18R,21S,22R>-N-<2-acetoxy-1-oxopropyl>-7,12,21,22-tetramethyl-10,16-bis<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3,20-dioxo-2,19,4-dioxaazatricyclo<16.3.1.0^5,21>docosa-6,8,12,14-tetraene
  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：

  1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-bis-ethylsulfanyl-propan-1-ol 在 咪唑 、 sodium hydroxide 、 三氟化硼乙醚 、 双氧水 、 sodium hydride 、 calcium carbonate 、 mercury dichloride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 54.08h， 生成 <4R-<4R*>>-<<1-<2-(2,2-dimethyl-1,3-dioxolan-4-yl)-2-<(4-methoxyphenyl)methoxy>ethyl>-2-methyl-3-butenyl>oxy>(1,1-dimethylethyl)diphenylsilane
  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

文献信息

• Total Synthesis of the Macrolide Antitumor Antibiotic Lankacidin C
  作者：Andrew S. Kende、Kun Liu、Istvan Kaldor、Gilbert Dorey、Kevin Koch

  DOI：10.1021/ja00136a025

  日期：1995.8

  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).