3(S)-trans-3,4-Bis<(benzoyloxy)methyl>cyclopentanone | 138804-29-2

• 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: 3(S)-trans-3,4-Bis<(benzoyloxy)methyl>cyclopentanone
• 英文别名: (3S,4S)-3,4-bis(benzoyloxymethyl)cyclopentan-1-one；trans-(3S,4S)-bis(benzoloxymethyl)cyclopentanone；(3S,4S)-3,4-di(benzoyloxymethyl)cyclopentanone；[(1S,2S)-2-(benzoyloxymethyl)-4-oxocyclopentyl]methyl benzoate
• CAS: 138804-29-2
• 化学式: C₂₁H₂₀O₅
• 分子量: 352.387
• InChiKey: IKDWYKXVCRWGOS-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3(S)-trans-3,4-Bis<(benzoyloxy)methyl>cyclopentanone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以97%的产率得到(3S,4S)-3,4-bis(benzoyloxymethyl)cyclopentan-1-ol
  参考文献：
  名称：

  New Routes to Isomerically Pure Cyclopentanes. Synthesis of (3S,4S)-3,4-Bis(benzoyloxymethyl)cyclopentan-1-ol using Palladium-Catalyzed [2 + 3] Cycloaddition

  摘要：

  本文介绍了获得对映体纯度为(3S,4S)-3,4-双(苯甲酰氧甲基)环戊烷-1-醇(6)的两种不同途径，该化合物是合成多种天然产物的有用中间体。2-(acetoxymethyl)-3-(trimethylsilyl)propene 与具有光学活性的甲基 (E)-3-O-benzyl-5、6-二脱氧-1，2-O-异亚丙基-δ-D-氧代-庚-5-enofuranuronate 或 (4R，Z)-4,5-(异亚丙基二氧基)戊-2-烯酸乙酯的光学活性。

  DOI：

  10.1055/s-1993-25815
• 作为产物：
  描述：

  (1S,2S)-3,3-二甲氧基-1,2-环丁烷二甲醇 在 吡啶 、 硫酸 作用下， 以 甲醇 、 乙醚 、 乙腈 为溶剂， 反应 35.0h， 生成 3(S)-trans-3,4-Bis<(benzoyloxy)methyl>cyclopentanone
  参考文献：
  名称：

  A Novel Approach toward the Synthesis of Chiral 2,3-Dideoxy Nucleosides and Their Carbocyclic Analogs

  摘要：

  Photochemical ring-expansion of chiral 2(S),3(R)-bis[(benzoyloxy) methyl] cyclobutanone (3) in the presence of alcohols and acidic N-H functional groups gives anomeric mixtures of acetals and N-amino acetals, respectively, with retention of stereochemistry of the ring substituents. In the presence of purine and 6-chloropurine the corresponding protected nucleosides are-obtained. The photoadduct with 6-chloropurine is converted to the known medicinally active deprotected adenine nucleoside with methanolic ammonia. One-carbon homologation of ketone 3 with diazomethane produces the corresponding optically pure cyclopentanone 8 with retention of stereochemistry. This ketone is converted to the optically pure cyclopentylamine 10 in two steps. Racemic amine 10 has been used as a key intermediate in the preparation of carbocyclic nucleosides.

  DOI：

  10.1021/jo00087a029

文献信息

• Synthesis of furanosyl compounds useful as intermediates in preparation
  申请人：Medivir AB

  公开号：US05473063A1

  公开（公告）日：1995-12-05

  Compounds of formulae ##STR1## wherein X is O; R.sup.1 is OH, phosphate, diphosphate, triphosphate or (CH.sub.2).sub.n --O--CH.sub.2 --O--P(.dbd.O)(OH).sub.2 wherein n is 0-2; R.sup.2 is H and R.sup.3 is CH.sub.3, CH.sub.2 OH, CH.sub.2 --O--CH.sub.3, CH.sub.2 SH, CH.sub.2 F or CH.sub.2 N.sub.3 ; or R3 is H and R.sup.2 is CH.sub.3, CH.sub.2 OH, CH.sub.2 --O--CH.sub.3, CH.sub.2 SH, CH.sub.2 F or CH.sub.2 N.sub.3 ; and Z is Cl, Br, I, acyloxy or alkoxy; are synthesized from acyclic intermediates and are subsequently useful in the preparation of nucleoside analogues with antiviral activity against retroviruses such as HIV and hepatitis B.

  化合物的公式为##STR1##其中X是O；R.sup.1是OH，磷酸盐，二磷酸盐，三磷酸盐或(CH.sub.2).sub.n --O--CH.sub.2 --O--P(.dbd.O)(OH).sub.2，其中n为0-2；R.sup.2为H，R.sup.3为CH.sub.3，CH.sub.2 OH，CH.sub.2 --O--CH.sub.3，CH.sub.2 SH，CH.sub.2 F或CH.sub.2 N.sub.3；或者R.sup.3为H，R.sup.2为CH.sub.3，CH.sub.2 OH，CH.sub.2 --O--CH.sub.3，CH.sub.2 SH，CH.sub.2 F或CH.sub.2 N.sub.3；Z为Cl、Br、I、酰氧基或烷氧基。这些化合物从非环状中间体合成，随后可用于制备抗逆转录病毒（如HIV和乙型肝炎）的核苷类似物。
• L-nucleoside analogues and pharmaceutical compositions
  申请人：Medivir AB

  公开号：US05747473A1

  公开（公告）日：1998-05-05

  ##STR1## Novel antiviral compounds of formulae (1A) and (1B), wherein X and R.sub.1 -R.sub.4 are as stated in claim 1 in the form of an .alpha.- or .beta.-anomer or a mixture thereof, and pharmaceutically acceptable salts thereof, are disclosed, as well as a new method for preparation thereof. Said compounds can be used for treatment of infections caused by viruses requiring reverse transcriptase for replication, such as HIV and hepatitis B virus.

  本发明公开了式（1A）和（1B）的新型抗病毒化合物，其中X和R.sub.1-R.sub.4如权利要求书中所述，以α-或β-异构体或其混合物的形式存在，并且其药物可接受的盐，以及其制备的新方法。所述化合物可用于治疗由需要反转录酶复制的病毒引起的感染，例如HIV和乙型肝炎病毒。
• Nucleoside derivatives
  申请人：Medivir AB

  公开号：US06121431A1

  公开（公告）日：2000-09-19

  ##STR1## Novel antiviral compounds of formulae (1A) and (1B), wherein X and R.sub.1 -R.sub.4 are as stated in claim 1 in the form of an .alpha.- or .beta.-anomer or a mixture thereof, and pharmaceutically acceptable salts thereof, are disclosed, as well as a new method for preparation thereof. Said compounds can be used for treatment of infections caused by viruses requiring reverse transcriptase for replication, such as HIV and hepatitis B virus.

  本发明涉及一种新型抗病毒化合物，其化学式为(1A)和(1B)，其中X和R.sub.1-R.sub.4如权利要求书1所述，以.alpha.-或.beta.-异构体或其混合物的形式存在，并且其药学上可接受的盐，以及一种新的制备方法。所述化合物可用于治疗由需要反转录酶复制的病毒引起的感染，例如HIV和乙型肝炎病毒。
• Rosenquist, Asa; Kvarnstroem, Ingemar; Svensson, Stefan C. T., Acta Chemica Scandinavica, 1992, vol. 46, # 11, p. 1127 - 1129
  作者：Rosenquist, Asa、Kvarnstroem, Ingemar、Svensson, Stefan C. T.、Classon, Bjoern、Samuelsson, Bertil

  DOI：——

  日期：——
• Janson Marianne, Kvarnstroem Ingemar, Svensson Stefan C. T., Classon Bjoe+, Synthesis, (1993) N 1, S 129-133
  作者：Janson Marianne, Kvarnstroem Ingemar, Svensson Stefan C. T., Classon Bjoe+

  DOI：——

  日期：——