tert-butyl (1S,2S,3E)-N-[2-hydroxy-1-(hydroxymethyl)-4-phenyl-3-butenyl]carbamate | 241478-42-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: tert-butyl (1S,2S,3E)-N-[2-hydroxy-1-(hydroxymethyl)-4-phenyl-3-butenyl]carbamate
• 英文别名: tert-butyl (1S,2S,3E)-2-hydroxy-1-(hydroxymethyl)-4-phenyl-3-butenylcarbamate；tert-butyl N-[(E,2S,3S)-1,3-dihydroxy-5-phenylpent-4-en-2-yl]carbamate
• CAS: 241478-42-2
• 化学式: C₁₆H₂₃NO₄
• 分子量: 293.363
• InChiKey: IHLYAQUWIHMWDH-KYXFNPKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S,2S,3E)-N-[2-hydroxy-1-(hydroxymethyl)-4-phenyl-3-butenyl]carbamate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 生成 (2S,3S,4E)-2-amino-5-phenyl-4-pentene-1,3-diol
  参考文献：
  名称：

  Effect of Aromatic Short-Chain Analogues of Ceramide on Axonal Growth in Hippocampal Neurons

  摘要：

  A series of D-erythro- and L-threo-ceramide analogues was synthesized and investigated for their ability to reverse the inhibitory effects of fumonisin B-1 (FB1) on axonal growth in hippocampal neurons. The analogues contained either a C-7 Side chain or a phenyl group substituted for the C-13 residue present in naturally occurring ceramides, while the N-acyl chain length was reduced from C-16-C-24 to C-2-C-8. D-erythro-Ceramide 18a with a C-7 Side chain and an N-acetyl residue and D-erythro-ceramide 20c with an aromatic side chain and an N-hexanoyl residue were most active in reversing the inhibitory effects of FB1 on axonal growth, although the mechanism remains unclear.

  DOI：

  10.1021/jm990091e
• 作为产物：
  描述：

  3-反-溴碳-2,2'-二甲基氧酸酯 在 溶剂黄146 、 zinc dibromide 作用下， 以 四氢呋喃 为溶剂， 反应 29.0h， 生成 tert-butyl (1S,2S,3E)-N-[2-hydroxy-1-(hydroxymethyl)-4-phenyl-3-butenyl]carbamate
  参考文献：
  名称：

  Synthesis and biological properties of novel sphingosine derivatives

  摘要：

  Sphingosine-1-phosphate (S-1P) derivatives such as threo-(2S,3S)-analogues, which are C-3 stereoisomers of natural erythro-(2S,3R)-S-1P, have been synthesized starting from L-serine or (IS,2S)-2-amino-1-aryl-1,3-propanediols (6). threo-(IS,2R)2-Amino-1-aryl-3-bromopropanols (HBr salt) have also been prepared from 6. The threo-S-1Ps and the threo-amino-bromide derivatives have shown potent inhibitory activity against Ca2+ ion mobilization in HL60 cells induced by erythro-S-1P, suggesting that these compounds would compete with cell surface EDG/S1P receptors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.12.010

文献信息

• Efficient stereodivergent synthesis of erythro- and threo-sphingosines: unprecedented reversal of the stereochemistry in the addition
  作者：Teiichi Murakami、Kiyotaka Furusawa

  DOI：10.1016/s0040-4020(02)01190-0

  日期：2002.11

  A convenient diastereoselective synthesis of d-erythro- and l-threo-sphingosine derivatives is described. l-Serine-derived aldehyde (Garner's aldehyde) (2) was treated with 1-alkenyl-zirconocene chlorides (3) in the presence of ZnBr2 in THF to give the natural erythro-(anti-) isomers with high diastereoselectivity (anti/syn=12–20:1). In contrast, reaction of 2 with 1-alkenyl-ethyl-zinc, prepared from

  的D-阿方便非对映选择性合成赤-和1-苏式-sphingosine衍生物进行说明。L-丝氨酸衍生的醛（加纳的醛）（2）与1-链烯基锆氯化物（处理3在ZnBr的存在下）2在THF中以得到天然赤- （反- ）具有高非对映选择性异构体（反/ syn = 12–20：1）。相反，2与由3和Et 2 Zn制备的1-烯基-乙基-锌在CH 2 Cl 2中的反应产生了不自然的苏氨酸-（syn-）异构体为主（anti / syn = 1：12-15）。
• Structure-activity relationship of short-chain sphingoid bases as inhibitors of sphingosine kinase
  作者：Steven De Jonghe、Ilse Van Overmeire、Samantha Poulton、Chris Hendrix、Roger Busson、Serge Van Calenbergh、Denis De Keukeleire、Sarah Spiegel、Piet Herdewijn

  DOI：10.1016/s0960-894x(99)00554-5

  日期：1999.11

  Short-chain sphinganine analogues 8, 9, 18, and 19 as well as 3-fluoro-sphingosine analogues 25 and 26 were synthesized. Their potential as sphingosine kinase inhibitors was investigated, in combination with previously synthesized sphingosine and fluorinated sphinganine analogues. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Effect of Aromatic Short-Chain Analogues of Ceramide on Axonal Growth in Hippocampal Neurons
  作者：Ilse Van Overmeire、Swetlana A. Boldin、Filip Dumont、Serge Van Calenbergh、Guido Slegers、Denis De Keukeleire、Anthony H. Futerman、Piet Herdewijn

  DOI：10.1021/jm990091e

  日期：1999.7.1

  A series of D-erythro- and L-threo-ceramide analogues was synthesized and investigated for their ability to reverse the inhibitory effects of fumonisin B-1 (FB1) on axonal growth in hippocampal neurons. The analogues contained either a C-7 Side chain or a phenyl group substituted for the C-13 residue present in naturally occurring ceramides, while the N-acyl chain length was reduced from C-16-C-24 to C-2-C-8. D-erythro-Ceramide 18a with a C-7 Side chain and an N-acetyl residue and D-erythro-ceramide 20c with an aromatic side chain and an N-hexanoyl residue were most active in reversing the inhibitory effects of FB1 on axonal growth, although the mechanism remains unclear.
• Synthesis and biological properties of novel sphingosine derivatives
  作者：Teiichi Murakami、Kiyotaka Furusawa、Tadakazu Tamai、Kazuyoshi Yoshikai、Masazumi Nishikawa

  DOI：10.1016/j.bmcl.2004.12.010

  日期：2005.2

  Sphingosine-1-phosphate (S-1P) derivatives such as threo-(2S,3S)-analogues, which are C-3 stereoisomers of natural erythro-(2S,3R)-S-1P, have been synthesized starting from L-serine or (IS,2S)-2-amino-1-aryl-1,3-propanediols (6). threo-(IS,2R)2-Amino-1-aryl-3-bromopropanols (HBr salt) have also been prepared from 6. The threo-S-1Ps and the threo-amino-bromide derivatives have shown potent inhibitory activity against Ca2+ ion mobilization in HL60 cells induced by erythro-S-1P, suggesting that these compounds would compete with cell surface EDG/S1P receptors. (C) 2004 Elsevier Ltd. All rights reserved.