Tetradecanoic acid (S)-2-benzyloxy-1-((S)-5-oxo-tetrahydro-furan-2-yl)-ethyl ester | 184873-71-0

• 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: Tetradecanoic acid (S)-2-benzyloxy-1-((S)-5-oxo-tetrahydro-furan-2-yl)-ethyl ester
• 英文别名: [(1S)-1-[(2S)-5-oxooxolan-2-yl]-2-phenylmethoxyethyl] tetradecanoate
• CAS: 184873-71-0
• 化学式: C₂₇H₄₂O₅
• 分子量: 446.627
• InChiKey: CRTOGKNDVQZABS-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  32
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Tetradecanoic acid (S)-2-benzyloxy-1-((S)-5-oxo-tetrahydro-furan-2-yl)-ethyl ester 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以92%的产率得到Tetradecanoic acid (S)-2-hydroxy-1-((S)-5-oxo-tetrahydro-furan-2-yl)-ethyl ester
  参考文献：
  名称：

  Conformationally Constrained Analogues of Diacylglycerol. 13. Protein Kinase C Ligands Based on Templates Derived from 2,3-Dideoxy-l-erythro(threo)-hexono-1,4-lactone and 2-Deoxyapiolactone

  摘要：

  In the present investigation, the last two possible modes of generating conformationally semirigid diacylglycerol (DAG) analogues embedded into five-membered ring lactones as templates III and IV are investigated. The first two templates studied in previous investigations corresponded to 2-deoxyribonolactone (template I) and 4,4-disubstituted gamma-butyrolactone (template II), with the latter producing potent protein kinase C (PK-C) ligands with low nanomolar binding affinities. The templates reported in this work correspond to 2,3-dideoxy-L-erythro- or -threo-hexono-1,4-lactone (template III) and 2-deoxyapiolactone (template IV). Compounds constructed with the dideoxy-L-erythro- or -threo-hexono-1,4-lactone template were synthesized stereospecifically from tri-O-acetyl-L-glucal and L-galactono-1,4-lactone, respectively. Compounds constructed with the 2-deoxyapiolactone template were synthesized stereoselectively from di-O-isopropylidene-alpha-D-apiose. Inhibition of the binding of [H-3]phorbol-12,13-dibutyrate to PK-C alpha showed that only the threo-isomer, 5-O-tetradecanoyl-2,3-dideoxy-L-threo-hexono-1,4-lactone (2) was a good PK-C ligand (K-i = 1 mu M). The rest of the ligands had poorer affinities with K-i values between 10 and 28 mu M. With these results, the order of importance of five-membered ring lactones as competent templates for the construction of semirigid DAG surrogates with effective PK-C binding affinity can be established as II much greater than I similar to III > IV.

  DOI：

  10.1021/jm960525v
• 作为产物：
  描述：

  (S)-5-((S)-1,2-dihydroxyethyl)dihydrofuran-2(3H)-one 在 吡啶 、 4-二甲氨基吡啶 、 二正丁基氧化锡 、 cesium fluoride 作用下， 以 二氯甲烷 为溶剂， 反应 54.0h， 生成 Tetradecanoic acid (S)-2-benzyloxy-1-((S)-5-oxo-tetrahydro-furan-2-yl)-ethyl ester
  参考文献：
  名称：

  Conformationally Constrained Analogues of Diacylglycerol. 13. Protein Kinase C Ligands Based on Templates Derived from 2,3-Dideoxy-l-erythro(threo)-hexono-1,4-lactone and 2-Deoxyapiolactone

  摘要：

  In the present investigation, the last two possible modes of generating conformationally semirigid diacylglycerol (DAG) analogues embedded into five-membered ring lactones as templates III and IV are investigated. The first two templates studied in previous investigations corresponded to 2-deoxyribonolactone (template I) and 4,4-disubstituted gamma-butyrolactone (template II), with the latter producing potent protein kinase C (PK-C) ligands with low nanomolar binding affinities. The templates reported in this work correspond to 2,3-dideoxy-L-erythro- or -threo-hexono-1,4-lactone (template III) and 2-deoxyapiolactone (template IV). Compounds constructed with the dideoxy-L-erythro- or -threo-hexono-1,4-lactone template were synthesized stereospecifically from tri-O-acetyl-L-glucal and L-galactono-1,4-lactone, respectively. Compounds constructed with the 2-deoxyapiolactone template were synthesized stereoselectively from di-O-isopropylidene-alpha-D-apiose. Inhibition of the binding of [H-3]phorbol-12,13-dibutyrate to PK-C alpha showed that only the threo-isomer, 5-O-tetradecanoyl-2,3-dideoxy-L-threo-hexono-1,4-lactone (2) was a good PK-C ligand (K-i = 1 mu M). The rest of the ligands had poorer affinities with K-i values between 10 and 28 mu M. With these results, the order of importance of five-membered ring lactones as competent templates for the construction of semirigid DAG surrogates with effective PK-C binding affinity can be established as II much greater than I similar to III > IV.

  DOI：

  10.1021/jm960525v

文献信息

• Conformationally Constrained Analogues of Diacylglycerol. 13. Protein Kinase C Ligands Based on Templates Derived from 2,3-Dideoxy-<scp>l</scp>-<i>erythro(threo)</i>-hexono-1,4-lactone and 2-Deoxyapiolactone
  作者：Jeewoo Lee、Nancy E. Lewin、Peter Acs、Peter M. Blumberg、Victor E. Marquez

  DOI：10.1021/jm960525v

  日期：1996.1.1

  In the present investigation, the last two possible modes of generating conformationally semirigid diacylglycerol (DAG) analogues embedded into five-membered ring lactones as templates III and IV are investigated. The first two templates studied in previous investigations corresponded to 2-deoxyribonolactone (template I) and 4,4-disubstituted gamma-butyrolactone (template II), with the latter producing potent protein kinase C (PK-C) ligands with low nanomolar binding affinities. The templates reported in this work correspond to 2,3-dideoxy-L-erythro- or -threo-hexono-1,4-lactone (template III) and 2-deoxyapiolactone (template IV). Compounds constructed with the dideoxy-L-erythro- or -threo-hexono-1,4-lactone template were synthesized stereospecifically from tri-O-acetyl-L-glucal and L-galactono-1,4-lactone, respectively. Compounds constructed with the 2-deoxyapiolactone template were synthesized stereoselectively from di-O-isopropylidene-alpha-D-apiose. Inhibition of the binding of [H-3]phorbol-12,13-dibutyrate to PK-C alpha showed that only the threo-isomer, 5-O-tetradecanoyl-2,3-dideoxy-L-threo-hexono-1,4-lactone (2) was a good PK-C ligand (K-i = 1 mu M). The rest of the ligands had poorer affinities with K-i values between 10 and 28 mu M. With these results, the order of importance of five-membered ring lactones as competent templates for the construction of semirigid DAG surrogates with effective PK-C binding affinity can be established as II much greater than I similar to III > IV.