benzyloxycarbonylamino(diethoxyphosphoryl)acetic acid (-)-8-phenylmenthyl ester | 917603-60-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyloxycarbonylamino(diethoxyphosphoryl)acetic acid (-)-8-phenylmenthyl ester
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] 2-diethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate
• CAS: 917603-60-2
• 化学式: C₃₀H₄₂NO₇P
• 分子量: 559.64
• InChiKey: PFELOTOSBDAFCG-IACUZNIESA-N

物化性质

• 沸点：
  663.3±55.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyloxycarbonylamino(diethoxyphosphoryl)acetic acid (-)-8-phenylmenthyl ester 在 正丁基锂 、 1,1,2,3-四甲基胍 、 二异丙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 31.83h， 生成 (2R,3E)-2-benzyl-2-benzyloxycarbonylaminododec-3-enoic acid (-)-8-phenylmenthyl ester
  参考文献：
  名称：

  Efficient Asymmetric Synthesis of Quaternary (E)-Vinylglycines by Deconjugative Alkylation of Dehydroamino Acids

  摘要：

  A two-step protocol for the asymmetric synthesis of protected quaternary (E)-vinylglycines from simple aldehydes is reported. The key step is a regiocontrolled deconjugative asymmetric alkylation of dehydroamino acids, giving the targets as single geometric isomers with high diastereoselectivity (92-96% de). The products can be converted to valuable quaternary beta-amino alcohols by chemoselective reduction.

  DOI：

  10.1021/ol062162r
• 作为产物：
  描述：

  N-CBZ-(二乙氧基磷酸基)氨基酸甲酯 在 4-二甲氨基吡啶 、 lithium hydroxide 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 96.0h， 生成 benzyloxycarbonylamino(diethoxyphosphoryl)acetic acid (-)-8-phenylmenthyl ester
  参考文献：
  名称：

  Efficient Asymmetric Synthesis of Quaternary (E)-Vinylglycines by Deconjugative Alkylation of Dehydroamino Acids

  摘要：

  A two-step protocol for the asymmetric synthesis of protected quaternary (E)-vinylglycines from simple aldehydes is reported. The key step is a regiocontrolled deconjugative asymmetric alkylation of dehydroamino acids, giving the targets as single geometric isomers with high diastereoselectivity (92-96% de). The products can be converted to valuable quaternary beta-amino alcohols by chemoselective reduction.

  DOI：

  10.1021/ol062162r

文献信息

• Total Synthesis of the Immunosuppressants Myriocin and 2-<i>epi</i>-Myriocin
  作者：Matthew C. Jones、Stephen P. Marsden

  DOI：10.1021/ol801709c

  日期：2008.9.18

  Total syntheses of the natural immunosuppressant myriocin (1) and the equipotent unnatural analogue 2-epi-myriocin (in protected form) have been achieved through a common strategy. The key transformations are the efficient synthesis of a quaternary (E)-vinylglycine by asymmetric deconjugative alkylation of a dehydroamino acid and an unusually highly diastereoselective dihydroxylation of the vinylglycine

  天然免疫抑制剂myriocin（1）和等价的非天然类似物2-epio-myriocin（处于保护状态）的总合成已通过一种常见策略实现。关键的转变是通过脱氢氨基酸的不对称去共轭烷基化和乙烯基甘氨酸烯烃的异常非对映选择性二羟基化来有效合成季（E）-乙烯基甘氨酸。
• Efficient Asymmetric Synthesis of Quaternary (<i>E</i>)-Vinylglycines by Deconjugative Alkylation of Dehydroamino Acids
  作者：Matthew C. Jones、Stephen P. Marsden、Dulce M. Muñoz Subtil

  DOI：10.1021/ol062162r

  日期：2006.11.1

  A two-step protocol for the asymmetric synthesis of protected quaternary (E)-vinylglycines from simple aldehydes is reported. The key step is a regiocontrolled deconjugative asymmetric alkylation of dehydroamino acids, giving the targets as single geometric isomers with high diastereoselectivity (92-96% de). The products can be converted to valuable quaternary beta-amino alcohols by chemoselective reduction.