2-((3aR,6S,6aR)-2,2-Dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-ethanol | 1026266-59-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((3aR,6S,6aR)-2,2-Dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-ethanol
• 英文别名: 2-[(3aR,6S,6aR)-6-ethenyl-2,2-dimethyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-yl]ethanol
• CAS: 1026266-59-0
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: KWYUTNHZEZERES-IQJOONFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((3aR,6S,6aR)-2,2-Dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-ethanol 在 chromium(VI) oxide 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 sodium perborate 、 samarium diiodide 、 dimethyl sulfide borane 、 Celite 、 硫酸 、 四丁基溴化铵 、 sodium hydride 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 silver carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙二醇 、 丙酮 、 苯 为溶剂， 反应 27.33h， 生成 tetradecyl 2-[(3S)-5-oxo-3-(2-phenylmethoxyethyl)oxolan-3-yl]acetate
  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：

  [(3aR,6aR)-2,2-Dimethyl-dihydro-furo[2,3-d][1,3]dioxol-(6E)-ylidene]-acetic acid methyl ester 在 copper(I) bromide dimethylsulfide complex 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.17h， 生成 2-((3aR,6S,6aR)-2,2-Dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-ethanol
  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.