tert-butyl (5S,6R)-5-tert-butyldimethylsilanyloxy-8-iodo-6-methylocta-2(E),7(E)-dienoate | 219606-78-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl (5S,6R)-5-tert-butyldimethylsilanyloxy-8-iodo-6-methylocta-2(E),7(E)-dienoate
• 英文别名: tert-butyl (2E,5S,6R,7E)-5-[tert-butyl(dimethyl)silyl]oxy-8-iodo-6-methylocta-2,7-dienoate
• CAS: 219606-78-7
• 化学式: C₁₉H₃₅IO₃Si
• 分子量: 466.475
• InChiKey: SOSLCNBKMNQMSX-LLMNSZGMSA-N

物化性质

• 沸点：
  425.7±45.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.25
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl (5S,6R)-5-tert-butyldimethylsilanyloxy-8-iodo-6-methylocta-2(E),7(E)-dienoate 在 4-二甲氨基吡啶 、 双(乙腈)氯化钯(II) 、 四丁基氟化铵 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.5h， 生成 tert-butyl (5S,6R)-5-[(2S)-2-[(2R)-3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-propionylamino]-2-methylpropionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate
  参考文献：
  名称：

  Total Synthesis of Cryptophycins-1, -3, -4, -24 (Arenastatin A), and -29, Cytotoxic Depsipeptides from Cyanobacteria of the Nostocaceae

  摘要：

  A convergent synthesis of cryptophycins has been developed in which (5S,GR)-5-hydroxy-6-methyl-8-phenylocta-2(E),7(E)-dienoic add (A) is coupled with an amino acid. segment (B). Two stereoselective routes to A are described, the first employing allylation of an alpha-homochiral aldehyde and the second using asymmetric crotylation of an achiral aldehyde to establish the two stereogenic centers present in a. The styryl moiety of A was attached either via Stille coupling or through a Wadsworth-Emmons condensation with diethyl benzylphosphonate. The amino acid subunit B was prepared from benzyl (2S)-2-hydroxyisocaproate by connection first to N-Boc-beta-alanine or its (2R)-methyl-substituted derivative and then to (2R)-N-Boc-O-methyltyrosine or its nt-chloro derivative. Fusion of the A and B subunits was accomplished by initial esterification of the former with the latter, followed by macrocyclization using diphenyl phosphorazidate. In this way, cryptophycin-3, -4, and -29 were obtained along with the nonnatural cyclic depsipeptide 52. Epoxidation of cryptophycin-3 with dimethyldioxirane gave cryptophycin-1; analogous epoxidation of 52 afforded arenastatin A (cryptophycin-24).

  DOI：

  10.1021/jo9907585
• 作为产物：
  描述：

  tert-butyl (5S,6R)-5-tert-butyldimethylsilanyloxy-7-hydroxy-6-methylhept-2(E)-enoate 在 chromium dichloride 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 tert-butyl (5S,6R)-5-tert-butyldimethylsilanyloxy-8-iodo-6-methylocta-2(E),7(E)-dienoate
  参考文献：
  名称：

  A concise synthesis of the cytotoxic depsipeptide arenastatin A

  摘要：

  Arenastatin A (1, cryptophycin 24) was synthesized by convergence of hydroxy eater 16 with amino acid derivative 27; two independent and highly efficient routes to 16 are disclosed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02014-0