2-hydroxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1-<(tert-butyldiphenylsilyl)oxy>-4-pentene | 172843-12-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-hydroxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1-<(tert-butyldiphenylsilyl)oxy>-4-pentene
• 英文别名: 1-[Tert-butyl(diphenyl)silyl]oxy-2-[[tert-butyl(diphenyl)silyl]oxymethyl]pent-4-en-2-ol
• CAS: 172843-12-8
• 化学式: C₃₈H₄₈O₃Si₂
• 分子量: 608.968
• InChiKey: ZBGREJXGRFTMES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.45
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1-<(tert-butyldiphenylsilyl)oxy>-4-pentene 在 dimethylsulfide borane complex 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以80 %的产率得到5-bis<<(tert-butyldiphenylsilyl)oxy>methyl>tetrahydro-2-furanone
  参考文献：
  名称：

  番茄酸和立体异构体的全合成（第 1 部分）：外消旋烯酰胺的双重不对称氢化

  摘要：

  据报道，外消旋烯酰胺的设计、合成和双不对称氢化可用于番茄酸及其异构体的立体发散合成。氢化结果（产率，ee）用于识别匹配和不匹配的产物，该信息对于阐明反应机理非常重要。还提出，如果反应机理已知，则无需通过匹配/不匹配分析进行光谱分析即可鉴定产物的结构。

  DOI：

  10.1016/j.tet.2023.133622
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 18.17h， 生成 2-hydroxy-2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1-<(tert-butyldiphenylsilyl)oxy>-4-pentene
  参考文献：
  名称：

  [EN] PROTEIN KINASE C AGONISTS
  [FR] AGONISTES DE PROTÉINE KINASE C

  摘要：

  本公开涉及某些二酰基甘油内酯化合物，包括该化合物的药物组合物，以及制备和使用该化合物和药物组合物的方法。本文所披露的化合物和组合物可用于治疗或预防可通过蛋白激酶C（PKC）激动剂调节的疾病、疾病或感染，如艾滋病。

  公开号：

  WO2020176505A1

文献信息

• [EN] PROTEIN KINASE C AGONISTS<br/>[FR] AGONISTES DE PROTÉINE KINASE C
  申请人：GILEAD SCIENCES INC

  公开号：WO2020176505A1

  公开（公告）日：2020-09-03

  The present disclosure relates generally to certain diacylglycerol lactone compounds, pharmaceutical compositions comprising said compounds, and methods of making and using said compounds and pharmaceutical compositions. The compounds and compositions disclosed herein may be used for the treatment or prevention of diseases, disorders, or infections modifiable by protein kinase C (PKC) agonists, such as HIV.

  本公开涉及某些二酰基甘油内酯化合物，包括该化合物的药物组合物，以及制备和使用该化合物和药物组合物的方法。本文所披露的化合物和组合物可用于治疗或预防可通过蛋白激酶C（PKC）激动剂调节的疾病、疾病或感染，如艾滋病。
• Conformationally Constrained Analogues of Diacylglycerol. 10. Ultrapotent Protein Kinase C Ligands Based on a Racemic 5-Disubstituted Tetrahydro-2-furanone Template
  作者：Rajiv Sharma、Jeewoo Lee、Shaomeng Wang、George W. A. Milne、Nancy E. Lewin、Peter M. Blumberg、Victor E. Marquez

  DOI：10.1021/jm950276v

  日期：1996.1.1

  5,5-Bis(hydroxymethyl)tetrahydro-2-furanone and its isomer 4,4-bis(hydroxymethyl)tetrahydro-2-furanone were investigated as possible templates for the construction of conformationally constrained analogues of the biologically important second messenger, diacylglycerol (DAG). The former lactone contains embedded within its structure an exact glycerol moiety, while in the latter the ring oxygen has been transposed to the other side of the carbonyl group. Al target compounds were synthesized as racemates from 1,3-dihydroxy-2-propanone. The 5,5-bis(hydroxymethyl)tetrahydro-2-furanone proved to be the better template for the construction of DAG surrogates that were demonstrated to have high binding affinities for the biological target, protein kinase C (PK-C). The simplest target compounds derived from this template (3e and 3f) have one of the hydroxyl moieties functionalized either as a myristate or as an oleate ester. The simplest target compound (9e) derived from the ineffective 4,4-bis(hydroxymethyl)tetrahydro-2-furanone template was investigated only with a myristoyl acyl chain. Reducing the long acyl chain to an acetyl moiety and attaching a compensating lipophilic chain to the lactone ring as an alpha-alkylidene moiety produced compounds 10e and 10f(Z-isomers) and 11e and 11f(E-isomers), which were constructed on the more effective 5,5-bis(hydroxymethyl)tetrahydro-2-furanone template. Targets 14c (Z-isomer) and 15c (E-isomer) were derived, in turn, from 4,4-bis(hydroxymethyl)tetrahydro-2-furan. The affinities of these ligands for PK-C were assessed in terms of their ability to displace bound [H-3-20]phorbol 12,13-dibutyrate (PDBU) from the single isozyme PK-C alpha. The biological data support the hypothesis that the increase in binding affinity for PK-C shown by some of these constrained DAG mimetics appears to be entropic in nature. Two of the designed ligands (10e and 10f) showed the highest affinities (34 and 24 nM, respectively) reported so far for a DAG analogue. Assuming that the interaction between these racemic compounds and PK-C is stereospecific, the potency of the active enantiomer is anticipated to double.
• Total synthesis of lycoperdic acid and stereoisomers (part 1): Double asymmetric hydrogenation of a racemic enamide
  作者：Kenji Morokuma、Kento Tanaka、Raku Irie、Masato Oikawa

  DOI：10.1016/j.tet.2023.133622

  日期：2023.10

  Design, synthesis, and double asymmetric hydrogenation of a racemic enamide are reported toward stereodivergent synthesis of lycoperdic acid and its isomers. The hydrogenation outcome (yield, ee) was used to identify matched and mismatched products, the information is important to clarify the reaction mechanism. It is also proposed that if the reaction mechanism is known, structure of the products would

  据报道，外消旋烯酰胺的设计、合成和双不对称氢化可用于番茄酸及其异构体的立体发散合成。氢化结果（产率，ee）用于识别匹配和不匹配的产物，该信息对于阐明反应机理非常重要。还提出，如果反应机理已知，则无需通过匹配/不匹配分析进行光谱分析即可鉴定产物的结构。