methyl 3,3-bis<(tert-butyldimethylsiloxy)methyl>acrylate | 172843-31-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3,3-bis<(tert-butyldimethylsiloxy)methyl>acrylate
• 英文别名: methyl 3,3-bis(t-butyldimethylsilyloxymethyl)acrylate；methyl 4-[tert-butyl(dimethyl)silyl]oxy-3-[[tert-butyl(dimethyl)silyl]oxymethyl]but-2-enoate；methyl 3,3-bis[(tert-butyldimethylsiloxy)methyl]acrylate
• CAS: 172843-31-1
• 化学式: C₁₈H₃₈O₄Si₂
• 分子量: 374.668
• InChiKey: PMLFDIGFNGJDDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3,3-bis<(tert-butyldimethylsiloxy)methyl>acrylate 在 吡啶 、 dimethyl sulfide borane 、 四丁基氟化铵 、 silica gel 、 sodium tert-pentoxide 、 二异丁基氢化铝 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 二甲基亚砜 、 苯 为溶剂， 反应 43.33h， 生成 9-[3,3-bis(hydroxymethyl)-2-methylenepropyl]-2-amino-6-chloropurine
  参考文献：
  名称：

  Synthesis of Unsaturated Carboacyclic Nucleoside Analogues via Mitsunobu Reactions

  摘要：

  2-Substituted allyl alcohols 9 and 14 were prepared starting from butane-1,2,4-triol and glycerol, respectively. Mitsunobu condensations of 9 and 14 with purine and pyrimidine bases, followed by deprotection, afforded a number of acyclonucleosides having 4-hydroxy-2-methylenebutyl or 3,3-bis(hydroxymethyl)-2-methylenepropyl chain.

  DOI：

  10.1080/15257770008033028
• 作为产物：
  描述：

  2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecan-6-ol 在 吡啶 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 54.0h， 生成 methyl 3,3-bis<(tert-butyldimethylsiloxy)methyl>acrylate
  参考文献：
  名称：

  Synthesis of Unsaturated Carboacyclic Nucleoside Analogues via Mitsunobu Reactions

  摘要：

  2-Substituted allyl alcohols 9 and 14 were prepared starting from butane-1,2,4-triol and glycerol, respectively. Mitsunobu condensations of 9 and 14 with purine and pyrimidine bases, followed by deprotection, afforded a number of acyclonucleosides having 4-hydroxy-2-methylenebutyl or 3,3-bis(hydroxymethyl)-2-methylenepropyl chain.

  DOI：

  10.1080/15257770008033028

文献信息

• Conformationally constrained diacylglycerol analogues
  申请人：The United States of America as represented by the Department of Health

  公开号：US05874464A1

  公开（公告）日：1999-02-23

  Conformationally constrained diacylglycerol analogues, pharmaceutical compositions comprising such analogues, and methods of using such analogues as agonists and antagonists of protein kinase C.

  构象受限的二酰基甘油类似物，包含这种类似物的药物组合物，以及使用这种类似物作为蛋白激酶C的激动剂和拮抗剂的方法。
• [EN] ANTI-VIRAL AND HEPATIC-TARGETED DRUGS<br/>[FR] MÉDICAMENTS ANTIVIRAUX ET CIBLÉS SUR LE FOIE
  申请人：AI BIOPHARMA

  公开号：WO2021074443A1

  公开（公告）日：2021-04-22

  Disclosed herein are identified compound fragments, compounds and their pharmaceutically acceptable salts, isotopes or solvates, useful as antiviral drug and/or as a hepatic-targeted drug, such as for the treatment of HBV, HDV and/or HIV. Formula (I).

  本文揭示了被识别的化合物片段、化合物及其药学上可接受的盐、同位素或溶剂化合物，用作抗病毒药物和/或肝靶向药物，例如用于治疗HBV、HDV和/或HIV。公式（I）。
• 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.