(2S,3S,4S)-3-Hydroxy-4-((S)-1-hydroxy-tetradecyl)-2-methyl-pyrrolidine-1-carboxylic acid benzyl ester | 878999-47-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,4S)-3-Hydroxy-4-((S)-1-hydroxy-tetradecyl)-2-methyl-pyrrolidine-1-carboxylic acid benzyl ester
• 英文别名: benzyl (2S,3S,4S)-3-hydroxy-4-[(1S)-1-hydroxytetradecyl]-2-methylpyrrolidine-1-carboxylate
• CAS: 878999-47-4
• 化学式: C₂₇H₄₅NO₄
• 分子量: 447.659
• InChiKey: NLENITVDEMZDTM-ZCLKUGBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  32
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-3-Hydroxy-4-((S)-1-hydroxy-tetradecyl)-2-methyl-pyrrolidine-1-carboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 12.5h， 以93%的产率得到(2S,3S,4S)-4-((S)-1-Hydroxy-tetradecyl)-2-methyl-pyrrolidin-3-ol
  参考文献：
  名称：

  Synthesis of 1-Deoxysphingosine Derivatives with Conformationally Restricted Pyrrolidinediol Head Groups

  摘要：

  A family of cyclic 1-deoxysphingolipid derivatives of structure 4 has been designed and synthesized, which may serve as tumorigenesis suppressors for various cancers. Compound 4 is a second-generation analogue developed from sphingosine (1), in which a hydroxyl substituent is moved from C1 to C5 and a methylene is added for conformational rigidity between the C2-nitrogen substituent and C4. The synthetic chemistry for pyrrolidine ring closure at C3-C4 features ring-closing metathesis followed by hydroboration-oxidation.

  DOI：

  10.1021/ol052839v
• 作为产物：
  描述：

  肉豆蔻醛 在 (H₂IMes)Cl₂Ru(CH-o-OiPrC₆H₄) 咪唑 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 L-(+)-酒石酸二异丙酯 、 dimethyl sulfide borane 、 四丁基氟化铵 、 sodium hydride 、 二异丁基氢化铝 、 二异丙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 癸烷 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 138.0h， 生成 (2S,3S,4S)-3-Hydroxy-4-((S)-1-hydroxy-tetradecyl)-2-methyl-pyrrolidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Synthesis of 1-Deoxysphingosine Derivatives with Conformationally Restricted Pyrrolidinediol Head Groups

  摘要：

  A family of cyclic 1-deoxysphingolipid derivatives of structure 4 has been designed and synthesized, which may serve as tumorigenesis suppressors for various cancers. Compound 4 is a second-generation analogue developed from sphingosine (1), in which a hydroxyl substituent is moved from C1 to C5 and a methylene is added for conformational rigidity between the C2-nitrogen substituent and C4. The synthetic chemistry for pyrrolidine ring closure at C3-C4 features ring-closing metathesis followed by hydroboration-oxidation.

  DOI：

  10.1021/ol052839v

文献信息

• Synthesis of 1-Deoxysphingosine Derivatives with Conformationally Restricted Pyrrolidinediol Head Groups
  作者：Ann M. Dougherty、Frank E. McDonald、Dennis C. Liotta、Steven J. Moody、David C. Pallas、Carrie D. Pack、Alfred H. Merrill

  DOI：10.1021/ol052839v

  日期：2006.2.1

  A family of cyclic 1-deoxysphingolipid derivatives of structure 4 has been designed and synthesized, which may serve as tumorigenesis suppressors for various cancers. Compound 4 is a second-generation analogue developed from sphingosine (1), in which a hydroxyl substituent is moved from C1 to C5 and a methylene is added for conformational rigidity between the C2-nitrogen substituent and C4. The synthetic chemistry for pyrrolidine ring closure at C3-C4 features ring-closing metathesis followed by hydroboration-oxidation.