(2S,3R,5S)-7-benzyloxy-5-(tert-butyldimethylsilyl)oxy-3-hydroxy-N-methoxy-2-methyl-N-methylheptanamide | 221627-43-6

• 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: (2S,3R,5S)-7-benzyloxy-5-(tert-butyldimethylsilyl)oxy-3-hydroxy-N-methoxy-2-methyl-N-methylheptanamide
• 英文别名: (2S,3R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-N-methoxy-N,2-dimethyl-7-phenylmethoxyheptanamide
• CAS: 221627-43-6
• 化学式: C₂₃H₄₁NO₅Si
• 分子量: 439.668
• InChiKey: IVGGTBUPKFDRGR-SESVDKBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  30.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  68.23
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,5S)-7-benzyloxy-5-(tert-butyldimethylsilyl)oxy-3-hydroxy-N-methoxy-2-methyl-N-methylheptanamide 在 palladium dihydroxide 2,6-二甲基吡啶 、 18-冠醚-6 、 potassium tert-butylate 、 氢气 、 4-甲基苯磺酸吡啶 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 53.5h， 生成 methyl 2-{(2R,3R,4R,6R)-4-(triisopropylsilyl)oxy-3-methyl-6-(2-oxoethyl)-2H-3,4,5,6-tetrahydropyran-2-yl}acetate
  参考文献：
  名称：

  Total Synthesis of Polycavernoside A, A Lethal Toxin of the Red Alga Polycavernosa tsudai

  摘要：

  Two approaches to the synthesis of the aglycon 120 of polycavernoside A (1) were developed, only one of which was completed. The successful "second-generation" route assembled the aglycon seco acids 102 and 106 via Nozaki-Hiyama-Kishi coupling of aldehyde 70, prepared from methyl (S)3-hydroxy-2-methylpropionate (72) and (S)-pantolactone (73), with vinyl bromide 71. The latter was obtained from a sequence which commenced from the silyl ether 24 of 3-hydroxypropionaldehyde and entailed cyclization of (Z)-zeta -hydroxy-alpha,beta-unsaturated ester 82. Regioselective Yamaguchi lactonization of trihydroxycarboxylic acids 102 and 106 and subsequent functional-group adjustments led to macrolactone 120, to which the fucopyranosylxylopyranoside moiety was attached. Stille coupling of the glycosidated aglycon 128 with dienylstannane 129 furnished polycavernoside A in a synthesis for which the longest linear sequence was 25 steps. The overall yield to lactone 120 was 4.7%.

  DOI：

  10.1021/jo0503862
• 作为产物：
  描述：

  isobutyl 5-(benzyloxy)-3-oxopentanoate 在 2,6-二甲基吡啶 、 Ru₂Cl₄((S)-BINAP)2 、 三氟甲磺酸二丁硼 、 氢气 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， -78.0~25.0 ℃ 、5.0 MPa 条件下， 生成 (2S,3R,5S)-7-benzyloxy-5-(tert-butyldimethylsilyl)oxy-3-hydroxy-N-methoxy-2-methyl-N-methylheptanamide
  参考文献：
  名称：

  Intramolecular palladium catalyzed alkoxy carbonylation of 6-hydroxy-1-octenes. Stereoselective synthesis of substituted tetrahydropyrans

  摘要：

  The reaction of hydroxy alkenes 5, 7, and 8 with CO and MeOH in the presence of PdCl2 and CuCl2 gave tetrahydropyrans 9, 11, and 12, respectively. Yields were dependent upon the configuration of substituents in the hydroxy alkene; in all cases, the tetrahydropyran was produced with 2,6-cis configuration. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02693-8