(4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxycyclohex-2-en-1-one | 247587-57-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxycyclohex-2-en-1-one
• 英文别名: trans-4-(tert-butyldimethylsiloxymethyl)-5-(tert-butyldimethylsiloxy)-2-cyclohexenone；(4r,5s)-4-Tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxy-cyclohex-2-en-1-one；(4R,5S)-5-[tert-butyl(dimethyl)silyl]oxy-4-[[tert-butyl(dimethyl)silyl]oxymethyl]cyclohex-2-en-1-one
• CAS: 247587-57-1
• 化学式: C₁₉H₃₈O₃Si₂
• 分子量: 370.68
• InChiKey: HTCPPCIDPSBRHS-WBVHZDCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxycyclohex-2-en-1-one 在 sodium tetrahydroborate 、 cerium(III) chloride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 7.0h， 生成 9-[(1S,4R,5S)-5-(tert-butyldimethylsilyloxy)-4-(tert-butyldimethylsilyloxymethyl)-2-cyclohexenyl]-2-amino-6-chloropurine
  参考文献：
  名称：

  （D）-和（L）-环己烯醇-G，一类新的抗病毒剂：合成，构象分析，分子建模和生物活性

  摘要：

  从（R）-香芹酮开始对映选择性地合成（D）-和（L）-环己烯基-G。两者均显示有效和选择性的抗疱疹病毒活性（HSV-1，HSV-2，VZV，CMV）。分子建模表明，两种异构体均以高能构象结合在HSV-1胸苷激酶的活性位点上，且碱基部分位于赤道位置。据信，环己烯环的柔韧性对其抗病毒活性至关重要。

  DOI：

  10.1081/ncn-100002360
• 作为产物：
  描述：

  (1R,2S,3S,5S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2-(tert-butyldimethylsilyloxymethyl)cyclohexanol 在 palladium on activated charcoal manganese(IV) oxide 、 甲酸铵 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxycyclohex-2-en-1-one
  参考文献：
  名称：

  （D）-和（L）-环己烯醇-G，一类新的抗病毒剂：合成，构象分析，分子建模和生物活性

  摘要：

  从（R）-香芹酮开始对映选择性地合成（D）-和（L）-环己烯基-G。两者均显示有效和选择性的抗疱疹病毒活性（HSV-1，HSV-2，VZV，CMV）。分子建模表明，两种异构体均以高能构象结合在HSV-1胸苷激酶的活性位点上，且碱基部分位于赤道位置。据信，环己烯环的柔韧性对其抗病毒活性至关重要。

  DOI：

  10.1081/ncn-100002360

文献信息

• CARBOCYCLIC NUCLEOSIDES AND PROCESS FOR OBTAINING SUCH
  申请人：Stichting REGA V.Z.W.

  公开号：EP1210347B1

  公开（公告）日：2004-06-23
• Enantioselective Synthesis and Conformational Study of Cyclohexene Carbocyclic Nucleosides
  作者：Jing Wang、Piet Herdewijn

  DOI：10.1021/jo9908288

  日期：1999.10.1

  Enantioselective synthesis of a new family of unsaturated six-membered carbocyclic nucleosides using (R)-(-)-can one as starting material is described. Introduction of the base moiety via Mitsunobu reaction proceeded regio- and stereoselectively and with good chemical yield, while the Pd-coupling approach failed. H-1 NMR study and molecular modeling show the adenine compound exists in an equilibrium of H-3(2) and H-2(3) conformers (ratio 7:3) in favor of the 3'-endo half-chair conformation, with the base oriented in a pseudoaxial position. This conformational preference can be explained by the pi --> sigma*(C1')-(N1) interaction involving the antibonding orbital of the C1'-N bond.
• Enantioselective Synthesis and Conformational Analysis of Cyclohexene Carbocyclic Nucleosides
  作者：Jing Wang、Piet Herdewijn

  DOI：10.1080/15257779908041505

  日期：1999.4

  An enantioselective approach towards the synthesis of optically pure cyclohexene nucleosides 3 has been developed starting from (R)-carvone. The key steps are the regio- and stereoselective hydroboration of an exo double bond, the selective reduction of an enone intermediate and introduction of a base moiety by Mitsunobu reaction. Conformational analysis showed that the adenine base adopts predominantly in a pseudo-axial position.
• Optically active trans-4-(tert-butyldimethylsiloxymethyl)-5-(tert-butyldimethylsiloxy)-2-cyclohexenone as a useful chiral building block for preparation of substituted cyclohexane rings: synthesis and its highly stereoselective reaction with RCu(CN)Li
  作者：Takeshi Hanazawa、Masakazu Koiwa、Georges P.-J. Hareau、Fumie Sato

  DOI：10.1016/s0040-4039(00)00239-2

  日期：2000.4

  Optically active trans-4-(tert-butyldimethylsiloxymethyl)-5-(tert-butyldimethylsiloxy)-2cyclohexenone (2) has been synthesized in 25% overall yield starting from easily available 1,4-bis(benzyloxy)-2,3-epoxy butane (3). The enone 2 reacts with excellent stereoselectivity with RCu(CN)Li thus working as an efficient chiral building block for preparation of substituted cyclohexane compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.
• (D)- AND (L)-CYCLOHEXENYL-G, A NEW CLASS OF ANTIVIRAL AGENTS: SYNTHESIS, CONFORMATIONAL ANALYSIS, MOLECULAR MODELING, AND BIOLOGICAL ACTIVITY
  作者：J. Wang、M. Froeyen、C. Hendrix、C. Andrei、R. Snoeck、E. Lescrinier、E. De Clercq、P. Herdewijn

  DOI：10.1081/ncn-100002360

  日期：2001.3.31

  (D)- and (L)-cyclohexeneyl-G were synthesized enantioselectively starting from (R)-carvone. Both show potent and selective anti-herpesvirus activity (HSV-1, HSV-2, VZV, CMV). Molecular modeling demonstrates that both isomers are bound in the active site of HSV-1 thymidine kinase in a high-energy conformation with the base moiety orienting in an equatorial position. It is believed that the flexibility

  从（R）-香芹酮开始对映选择性地合成（D）-和（L）-环己烯基-G。两者均显示有效和选择性的抗疱疹病毒活性（HSV-1，HSV-2，VZV，CMV）。分子建模表明，两种异构体均以高能构象结合在HSV-1胸苷激酶的活性位点上，且碱基部分位于赤道位置。据信，环己烯环的柔韧性对其抗病毒活性至关重要。