allyl (2S)-2-({3-[(tert-butoxycarbonyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate | 186193-09-9

• 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: allyl (2S)-2-({3-[(tert-butoxycarbonyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate
• 英文别名: prop-2-enyl (2S)-2-[2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]oxy-4-methylpentanoate
• CAS: 186193-09-9
• 化学式: C₁₉H₃₃NO₆
• 分子量: 371.474
• InChiKey: LJFMETOVFKSCHV-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl (2S)-2-({3-[(tert-butoxycarbonyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate 在 四(三苯基膦)钯 吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 35.75h， 生成 (1S,3Z)-1-allyl-4-iodo-4-phenylbut-3-enyl (2S)-2-({3-[(N-acryloyl-3-chloro-O-methyl-D-tyrosyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate
  参考文献：
  名称：

  Total Synthesis of Cryptophycin Analogues via a Scaffold Approach

  摘要：

  Allylation of in situ generated beta,gamma-unsaturated aldehydes affords rapid access to vinyl halide analogues of fragment A of the cryptophycins. Three scaffolds are prepared in gram quantities by a ring-closing metathesis approach. Derivatization via a variety of cross-coupling protocols is possible, which affords novel analogues of these potent antimitotic agents.

  DOI：

  10.1021/ol0609356
• 作为产物：
  描述：

  L-alpha-羟基异己酸 在 4-二甲氨基吡啶 、 四丁基氯化铵 、 sodium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 32.0h， 生成 allyl (2S)-2-({3-[(tert-butoxycarbonyl)amino]-2,2-dimethylpropanoyl}oxy)-4-methylpentanoate
  参考文献：
  名称：

  Total Synthesis of Cryptophycin Analogues via a Scaffold Approach

  摘要：

  Allylation of in situ generated beta,gamma-unsaturated aldehydes affords rapid access to vinyl halide analogues of fragment A of the cryptophycins. Three scaffolds are prepared in gram quantities by a ring-closing metathesis approach. Derivatization via a variety of cross-coupling protocols is possible, which affords novel analogues of these potent antimitotic agents.

  DOI：

  10.1021/ol0609356

文献信息

• A novel approach for total synthesis of cryptophycins via asymmetric crotylboration protocol
  作者：Ulhas P. Dhokte、Vien V. Khau、Darrell R. Hutchison、Michael J. Martinelli

  DOI：10.1016/s0040-4039(98)01994-7

  日期：1998.11

  Acyclic and a highly efficient stereoselective CC bond formation of aldehyde3 with the crotylboron reagent4, derived from (−)-α-pinene, provided a homoallylic alcohol6 in ≥99% enantio-(ee) and diastereomeric excess (de). The alcohol6 was linearly converted into the desired Fragment A10 of cryptophycins in seven steps. This enantiomerically pure Fragment A was conveniently and efficiently coupled with

  与衍生自（-）-α-derived烯的巴豆基硼试剂4形成醛3的无环且高效的立体选择性CC键，可提供≥99％对映体（ee）和非对映体过量（de）的均烯丙基醇6。通过七个步骤将醇6线性转化为所需的隐藻霉素片段A 10。该对映体纯的片段A方便且有效地与其他三个片段，即B，C和D偶联，并提供了所需的隐藻霉素A衍生物（LY404291）。进一步阐述了LY404291中的末端双键以提供末端环氧化物LY404292和隐藻素。51和52。
• Total Synthesis of Cryptophycin Analogues via a Scaffold Approach
  作者：J. Adam McCubbin、Matthew L. Maddess、Mark Lautens

  DOI：10.1021/ol0609356

  日期：2006.7.1

  Allylation of in situ generated beta,gamma-unsaturated aldehydes affords rapid access to vinyl halide analogues of fragment A of the cryptophycins. Three scaffolds are prepared in gram quantities by a ring-closing metathesis approach. Derivatization via a variety of cross-coupling protocols is possible, which affords novel analogues of these potent antimitotic agents.