Dibenzyl (3R,4S)-4-(benzyloxy)-3-hydroxypentanephosphonate | 150934-77-3

• 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: Dibenzyl (3R,4S)-4-(benzyloxy)-3-hydroxypentanephosphonate
• 英文别名: (3R,4S)-1-bis(phenylmethoxy)phosphoryl-4-phenylmethoxypentan-3-ol
• CAS: 150934-77-3
• 化学式: C₂₆H₃₁O₅P
• 分子量: 454.503
• InChiKey: IXLQECXGODSKMS-BKMJKUGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  Dibenzyl (3R,4S)-4-(benzyloxy)-3-hydroxypentanephosphonate 在 palladium on activated charcoal 盐酸 、 乙醇 、 四丁基碘化铵 、 环己烯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 1-<<(4(S)-hydroxy-1-phosphonyl)-3(R)-pentoxy>methyl>thymine
  参考文献：
  名称：

  Synthesis of Phosphonate Isosteres of 2‘-Deoxy-1‘,2‘-seco-nucleotides

  摘要：

  Practical and convergent syntheses of 2'-deoxy-1',2'-seco-nucleophosphonates and 1',2'-seco-nucleophosphonates are described. Phosphonate chirons derived from D-isoascorbic acid were used in alkylation of functionalized nucleobases to provide the title phosphonate isosteres in good yields. Subsequent deprotection and deesterification led to the 5'-C-methylenephosphonic acids which were conveniently purified using gravity flow C-18 reverse phase column chromatography.

  DOI：

  10.1021/jo951701v
• 作为产物：
  描述：

  膦酸,甲基-,二(苯基甲基)酯 、 (2R,3S)-3-(benzyloxy)-1,2-epoxybutane 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以84%的产率得到Dibenzyl (3R,4S)-4-(benzyloxy)-3-hydroxypentanephosphonate
  参考文献：
  名称：

  A general and facile synthesis of .beta.- and .gamma.-hydroxy phosphonates from epoxides

  摘要：

  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.

  DOI：

  10.1021/jo00073a043

文献信息

• Synthesis of Phosphonate Isosteres of 2‘-Deoxy-1‘,2‘-seco-nucleotides
  作者：Hussein I. El-Subbagh、Saibaba Racha、Elie Abushanab、Raymond P. Panzica

  DOI：10.1021/jo951701v

  日期：1996.1.1

  Practical and convergent syntheses of 2'-deoxy-1',2'-seco-nucleophosphonates and 1',2'-seco-nucleophosphonates are described. Phosphonate chirons derived from D-isoascorbic acid were used in alkylation of functionalized nucleobases to provide the title phosphonate isosteres in good yields. Subsequent deprotection and deesterification led to the 5'-C-methylenephosphonic acids which were conveniently purified using gravity flow C-18 reverse phase column chromatography.
• 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.