tert-butyl N-[3-[bis(2-cyanoethoxy)phosphoryloxymethyl]-4-hydroxynonadec-1-en-3-yl]carbamate | 169324-64-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: tert-butyl N-[3-[bis(2-cyanoethoxy)phosphoryloxymethyl]-4-hydroxynonadec-1-en-3-yl]carbamate
• CAS: 169324-64-5
• 化学式: C₃₁H₅₆N₃O₇P
• 分子量: 613.775
• InChiKey: UZTMSFSTXUJAMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.26
• 重原子数：
  42.0
• 可旋转键数：
  26.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  150.9
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[3-[bis(2-cyanoethoxy)phosphoryloxymethyl]-4-hydroxynonadec-1-en-3-yl]carbamate 在 氨 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.5h， 生成 2-vinyl dihydrosphingosine-1-phosphate
  参考文献：
  名称：

  Synthesis of an inhibitor of sphingosine-1-phosphate lyase

  摘要：

  The 2-vinyl dihydrosphingosine-1-phosphate 1 was synthesized and tested for inhibition of sphingosine-l-phosphate lyase. The carbon skeleton was prepared by acylation of a methionine imine with N-methoxy-N-methyl palmitamide. The vinyl group was generated by thermal sulfoxide elimination. Reduction of both carbonyl groups and deprotection gave 2-vinyl dihydrosphingosine. The phosphate group was introduced by means of bis(2-cyanoethyl)-N,N-diisopropyl-phosphoramidite as monofunctional phosphitylation reagent.

  DOI：

  10.1016/s0040-4039(00)75971-5
• 作为产物：
  描述：

  2-(2-Methanesulfinyl-ethyl)-3-oxo-2-(2,2,2-trifluoro-acetylamino)-octadecanoic acid methyl ester 在 四氮唑 、 4-二甲氨基吡啶 、 calcium borohydride 、 碘 作用下， 以 四氢呋喃 、 乙醇 、 xylene 为溶剂， 反应 26.25h， 生成 tert-butyl N-[3-[bis(2-cyanoethoxy)phosphoryloxymethyl]-4-hydroxynonadec-1-en-3-yl]carbamate
  参考文献：
  名称：

  Synthesis of an inhibitor of sphingosine-1-phosphate lyase

  摘要：

  The 2-vinyl dihydrosphingosine-1-phosphate 1 was synthesized and tested for inhibition of sphingosine-l-phosphate lyase. The carbon skeleton was prepared by acylation of a methionine imine with N-methoxy-N-methyl palmitamide. The vinyl group was generated by thermal sulfoxide elimination. Reduction of both carbonyl groups and deprotection gave 2-vinyl dihydrosphingosine. The phosphate group was introduced by means of bis(2-cyanoethyl)-N,N-diisopropyl-phosphoramidite as monofunctional phosphitylation reagent.

  DOI：

  10.1016/s0040-4039(00)75971-5