N-Boc 2-vinyl dihydrosphingosine | 169324-81-6

• 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: N-Boc 2-vinyl dihydrosphingosine
• 英文别名: tert-butyl N-[4-hydroxy-3-(hydroxymethyl)nonadec-1-en-3-yl]carbamate
• CAS: 169324-81-6
• 化学式: C₂₅H₄₉NO₄
• 分子量: 427.668
• InChiKey: NINJPGINTWFEDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.27
• 重原子数：
  30.0
• 可旋转键数：
  18.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  78.79
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-Boc 2-vinyl dihydrosphingosine 在 四氮唑 、 氨 、 碘 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.75h， 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：

  methyl 2-trifluoro acetamido-2-vinyl nonadecanoate-3-one 在 4-二甲氨基吡啶 、 calcium borohydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 23.0h， 生成 N-Boc 2-vinyl dihydrosphingosine
  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

文献信息

• Method for preparation of sphingoid bases
  申请人：The United States of America represented by the Department of Health and

  公开号：US05430169A1

  公开（公告）日：1995-07-04

  The present invention provides a series of non-toxic compounds which function to inhibit the activity of S-1-P aldolase in respect to its cleavage of S-1-P. These inhibitors are described by the compounds of formula I ##STR1## wherein R is a radical containing 1 to 15 carbon atoms, a halogen, or hydrocarbon, R' is an organic radical or hydrogen, and R" is --NH.sub.3.sup.+ or --NH--NH .sup.+, with the proviso that, when R is CH.sub.3 (CH).sub.12 (CH.dbd.CH) and R' is hydrogen, R" is --NH--NH.sub.3.sup.+. A method for preparing such compounds, which may generally be described as 1-phosphate derivatives of compounds which include a 2-amino-1,3-alcohol radical is also disclosed.

  本发明提供了一系列无毒化合物，其功能是抑制S-1-P醛缩酶在其对S-1-P的裂解方面的活性。这些抑制剂由式I的化合物描述：##STR1##其中R是含有1至15个碳原子，卤素或碳氢基团的基团，R'是有机基团或氢，R"是--NH.sub.3.sup.+或--NH--NH .sup.+，但是当R为CH.sub.3 (CH).sub.12 (CH.dbd.CH)且R'为氢时，R"为--NH--NH.sub.3.sup.+。还公开了一种制备这种化合物的方法，该方法通常可以描述为包括2-氨基-1,3-醇基团的化合物的1-磷酸酯衍生物。