(R)-4-chloro-2-(methoxymethoxy)butyl benzoate | 150943-38-7

• 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: (R)-4-chloro-2-(methoxymethoxy)butyl benzoate
• 英文别名: [(2R)-4-chloro-2-(methoxymethoxy)butyl] benzoate
• CAS: 150943-38-7
• 化学式: C₁₃H₁₇ClO₄
• 分子量: 272.729
• InChiKey: ZTTVPEUBWYUKJJ-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (R)-4-chloro-2-(methoxymethoxy)butyl benzoate 在 苯磺酰胺 、 三氟甲磺酸三甲基硅酯 、 sodium iodide 作用下， 以 丁酮 为溶剂， 反应 5.25h， 生成 (R)-2-((2-acetamido-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4-iodobutyl benzoate
  参考文献：
  名称：

  An Enantiospecific Synthesis of the Human Cytomegalovirus Antiviral Agent [(R)-3-((2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4- hydroxybutyl]phosphonic Acid

  摘要：

  The racemic isosteric phosphonate of ganciclovir monophosphate (BW2482U89, SR3745, [3-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4-hydroxybutyl]phosphonic acid, 1) has potent and selective in vitro;activity against human cytomegalovirus. An enantiospecific synthesis of the R-enantiomer of compound 1 starting from L-arabinose was developed. The synthesis involved (1) the preparation of a chiral acyclic moiety, (2) the coupling of the chiral acyclic moiety to diacetylguanine, (3) the introduction; of phosphorus, and (4) the final deprotection. The R-enantiomer, which has stereochemistry analogous to the natural compound GMP, was tested against human cytomegalovirus and had an IC50 Of 1.7 mu M, which was approximately 2-fold more active than the racemic material. Both racemic and chiral compounds were less toxic than ganciclovir to bone marrow progenitor cells in an in vitro assay.

  DOI：

  10.1021/jm00035a018
• 作为产物：
  描述：

  2-benzoyloxyacetaldehyde 在 四氯化碳 、 臭氧 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 16.0h， 生成 (R)-4-chloro-2-(methoxymethoxy)butyl benzoate
  参考文献：
  名称：

  Enantioselective allyltitanations. Synthesis of optically active 1,2-diol units: useful intermediates for the preparation of biologically active compounds

  摘要：

  1,2-Diol units were synthesized with excellent enantiomeric excess by using an enantioselective allyltitanation of alpha-alkoxy-substituted aldehydes. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00390-0

文献信息

• [EN] THERAPEUTIC NUCLEOSIDES
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：WO1993006112A1

  公开（公告）日：1993-04-01

  (EN) The present invention relates to an antiviral phosphonate derivate of an acyclic purine nucleoside analog, to pharmaceutically acceptable derivatives thereof and to their use in medical therapy, particularly in the treatment of cytomegalovirus infections. Methods for preparing the R-enantiomer of the compound of the invention, substantially free from the corresponding S-enantiomer are disclosed.(FR) La présente invention se rapporte à un dérivé de phosphonate antiviral d'un analogue de nucléoside de purine acyclique, à des dérivés pharmaceutiquement acceptables, ainsi qu'à leur utilisation en thérapie médicale, en particulier pour le traitement d'infections par cytomégalovirus. Des procédés de préparation de l'énantiomère-R du composé de l'invention, lequel est pratiquement dépourvu de l'énantiomère-S correspondant, sont également décrits.
• Enantioselective allyltitanations. Synthesis of optically active 1,2-diol units: useful intermediates for the preparation of biologically active compounds
  作者：Janine Cossy、Samir Bouzbouz、Jean Claude Caille

  DOI：10.1016/s0957-4166(99)00390-0

  日期：1999.10

  1,2-Diol units were synthesized with excellent enantiomeric excess by using an enantioselective allyltitanation of alpha-alkoxy-substituted aldehydes. (C) 1999 Elsevier Science Ltd. All rights reserved.
• An Enantiospecific Synthesis of the Human Cytomegalovirus Antiviral Agent [(R)-3-((2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4- hydroxybutyl]phosphonic Acid
  作者：Stanley D. Chamberlain、Karen K. Biron、Ronna E. Dornsife、Devron R. Averett、Lilia Beauchamp、George W. Koszalka

  DOI：10.1021/jm00035a018

  日期：1994.4

  The racemic isosteric phosphonate of ganciclovir monophosphate (BW2482U89, SR3745, [3-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4-hydroxybutyl]phosphonic acid, 1) has potent and selective in vitro;activity against human cytomegalovirus. An enantiospecific synthesis of the R-enantiomer of compound 1 starting from L-arabinose was developed. The synthesis involved (1) the preparation of a chiral acyclic moiety, (2) the coupling of the chiral acyclic moiety to diacetylguanine, (3) the introduction; of phosphorus, and (4) the final deprotection. The R-enantiomer, which has stereochemistry analogous to the natural compound GMP, was tested against human cytomegalovirus and had an IC50 Of 1.7 mu M, which was approximately 2-fold more active than the racemic material. Both racemic and chiral compounds were less toxic than ganciclovir to bone marrow progenitor cells in an in vitro assay.