diethyl 4-O-benzyl-3,4-dihydroxybutylphosphonate | 150934-78-4

• 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: diethyl 4-O-benzyl-3,4-dihydroxybutylphosphonate
• 英文别名: Diethyl 4-(benzyloxy)-3-hydroxybutanephosphonate；4-Diethoxyphosphoryl-1-phenylmethoxybutan-2-ol
• CAS: 150934-78-4
• 化学式: C₁₅H₂₅O₅P
• 分子量: 316.334
• InChiKey: IWYWYVINQXNANP-UHFFFAOYSA-N

物化性质

• 沸点：
  450.3±40.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 4-O-benzyl-3,4-dihydroxybutylphosphonate 在 palladium dihydroxide silver(l) oxide 作用下， 以 乙醇 、 二氯甲烷 、 环己烯 为溶剂， 生成 (4-Hydroxy-3-methoxy-butyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Phosphonate isosteres of phospholipids

  摘要：

  A facile synthesis of phosphonolipid isosteres of the platelet activating factor(PAF) and the anticancer ether lipid ET-O-18 is described.

  DOI：

  10.1016/s0040-4039(00)73630-6
• 作为产物：
  描述：

  苯甲醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 、 正丁基锂 、 三氟化硼乙醚 、 四丁基硫酸氢铵 作用下， 反应 5.17h， 生成 diethyl 4-O-benzyl-3,4-dihydroxybutylphosphonate
  参考文献：
  名称：

  Synthesis of Acyclonucleoside Phosphonates as Antiviral Agents Against Cytomegalovirus

  摘要：

  Phosphonic acid analogs of ACV and DHPG that are isosteric with ACV phosphate and DHPG phosphate have been synthesized and evaluated for antiviral activity against human, murine. and guinea pig strains of cytomegalovirus. The phosphonates showed high activity against all of the strains. They were also evaluated against a DHPG resistant strain of human cytomegalovirus. Although the activity dropped considerably, significant antiviral activity was still evident.

  DOI：

  10.1080/15257779408013261

文献信息

• A general and facile synthesis of .beta.- and .gamma.-hydroxy phosphonates from epoxides
  作者：Zhengong Li、Saibaba Racha、Li Dan、Hussein El-Subbagh、Elie Abushanab

  DOI：10.1021/jo00073a043

  日期：1993.10

  A practical and facile method for the preparation of hydroxy phosphonate esters is described. Regiospecific ring opening of monosubstituted epoxides by phosphorus and carbon nucleophiles, derived from diethyl phosphite and methanephosphonates, in the presence of BF3.OEt2 furnishes the corresponding beta- and gamma-hydroxy phosphonates, respectively. Ketals, bromides, sulfonate esters, and carbamates (compounds 12, 13, 15, 16, and 18) are stable under the reaction conditions, but benzoate esters(14) behave differently. While they survive phosphite nucleophilicity, they are cleaved by phosphonates. Several chirons (2, 28a, 30b, and 31) for the synthesis of phosphonate isosteres of nucleotides and phospholipids are also described.
• US5532225A
  申请人：——

  公开号：US5532225A

  公开（公告）日：1996-07-02
• [EN] ACYCLIC PURINE PHOSPHONATE NUCLEOTIDE ANALOGS AS ANTIVIRAL AGENTS, AND RELATED SYNTHETIC METHODS<br/>[FR] ANALOGUES DE NUCLEOTIDES PHOSPHONATES DE PURINE ACYCLIQUE UTILES COMME AGENTS ANTIVIRAUX ET PROCEDES SYNTHETIQUES CONNEXES
  申请人：SRI INTERNATIONAL

  公开号：WO1994003466A1

  公开（公告）日：1994-02-17

  (EN) Acyclic purine phosphonate nucleotide analogs useful to treat herpes viral infections are provided in enantiomerically pure form. These antiviral agents have structural formula (Ia) or (Ib), and may be in acid, salt or ester form. Such compounds may also be dehydrated to provide antiviral agents in cyclic form. Pharmaceutical compositions are provided containing the antiviral agents, as is a chiral synthesis which may be used to prepare the agents in enantiomerically pure form or as a racemic mixture.(FR) Des analogues de nucléotides phosphonatés de purine acyclique utilisés dans le traitement des infections virales de l'herpès sont obtenus sous une forme énantiomériquement pure. Ces agents antiviraux ont la formule structurelle (Ia) ou (Ib) et peuvent être sous forme d'acides, de sels ou d'esters. Ces composés peuvent également être déshydratés afin d'obtenir des agents antiviraux sous forme cyclique. On produit également des compositions pharmaceutiques contenant les agents antiviraux comme dans une synthèse chirale qui peut être utilisée pour préparer les agents sous forme énantiomériquement pure ou comme mélange racémique.
• [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.
• Synthesis of Acyclonucleoside Phosphonates as Antiviral Agents Against Cytomegalovirus
  作者：Elmer J. Reist、Wallace W. Bradford、Beatrice L. Ruhland-Fritsch、Priscilla A. Sturm、Nurulain T. Zaveri、John Huffman、Robert W. Sidwell

  DOI：10.1080/15257779408013261

  日期：1994.3

  Phosphonic acid analogs of ACV and DHPG that are isosteric with ACV phosphate and DHPG phosphate have been synthesized and evaluated for antiviral activity against human, murine. and guinea pig strains of cytomegalovirus. The phosphonates showed high activity against all of the strains. They were also evaluated against a DHPG resistant strain of human cytomegalovirus. Although the activity dropped considerably, significant antiviral activity was still evident.