(R)-[[1-[[(甲基磺酰)氧]甲基]-2-苄氧基乙氧基]甲基]膦酸二乙酯 | 120362-30-3

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (R)-[[1-[[(甲基磺酰)氧]甲基]-2-苄氧基乙氧基]甲基]膦酸二乙酯
• 中文别名: [[1-[[(甲磺酰基)氧基]甲基]-2-(苯甲氧基)乙氧基]甲基]-(R)-磷酸-二乙酯
• 英文名称: (R)-3-O-Benzyl-2-O-<(diethylphosphonyl)methyl>-1-O-(methylsulfonyl)glycerol
• 英文别名: (R)-[[1-[[(Methylsulfonyl)oxy]methyl]-2-(phenylmethoxy)ethoxy]methyl]phosphonic acid diethyl ester；[(2R)-2-(diethoxyphosphorylmethoxy)-3-phenylmethoxypropyl] methanesulfonate
• CAS: 120362-30-3
• 化学式: C₁₆H₂₇O₈PS
• 分子量: 410.425
• InChiKey: GXAKNYJUUKMDPM-MRXNPFEDSA-N

物化性质

• 沸点：
  554.9±50.0 °C(Predicted)
• 密度：
  1.237

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-[[1-[[(甲基磺酰)氧]甲基]-2-苄氧基乙氧基]甲基]膦酸二乙酯 在 palladium dihydroxide potassium carbonate 、 环己烯 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 (S)-1-<3-Hydroxy-2-<(diethylphosphonyl)methoxy>propyl>cytosine
  参考文献：
  名称：

  Synthesis and antiviral activity of the nucleotide analog (S)-1-[3-hydroxy-2-(phosphonylmethoxy)propyl]cystosine

  摘要：

  The acyclic nucleotide analogue (S)-1-[3-hydroxy-2-(phosphonylmethoxy)propyl] cytosine (2, HPMPC) was prepared on a multigram scale in 18% overall yield starting from (R)-2,3-O-isopropylideneglycerol. The key step in the nine-step synthetic route is coupling of cytosine with the side-chain derivative 8 which bears a protected phosphonylmethyl ether group. In vitro data showed that HPMPC has good activity against herpes simplex virus types 1 and 2, although it was 10-fold less potent than acyclovir [AVC, 9-[(2-hydroxyethoxy)methyl]guanine]. By comparison, HPMPC exhibited greater activity than ACV against a thymidine kinase deficient strain of HSV 1 and was more potent than ganciclovir [DHPG, 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine] against human cytomegalovirus. In vivo, HPMPC showed exceptional potency against HSV 1 systemic infection in mice, having an ED50 of 0.1 mg/kg per day (ip) compared with 50 mg/kg per day for ACV. HPMPC was also more efficacious than ACV in the topical treatment of HSV 1 induced cutaneous lesions in guinea pigs.

  DOI：

  10.1021/jm00127a010
• 作为产物：
  描述：

  (R)-4-苄氧甲基-2,2-二甲基-1,3-二氧戊环 在 4-二甲氨基吡啶 、 amberlyst-15 、 硫酸 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 75.5h， 生成 (R)-[[1-[[(甲基磺酰)氧]甲基]-2-苄氧基乙氧基]甲基]膦酸二乙酯
  参考文献：
  名称：

  Synthesis and antiviral activity of the nucleotide analog (S)-1-[3-hydroxy-2-(phosphonylmethoxy)propyl]cystosine

  摘要：

  The acyclic nucleotide analogue (S)-1-[3-hydroxy-2-(phosphonylmethoxy)propyl] cytosine (2, HPMPC) was prepared on a multigram scale in 18% overall yield starting from (R)-2,3-O-isopropylideneglycerol. The key step in the nine-step synthetic route is coupling of cytosine with the side-chain derivative 8 which bears a protected phosphonylmethyl ether group. In vitro data showed that HPMPC has good activity against herpes simplex virus types 1 and 2, although it was 10-fold less potent than acyclovir [AVC, 9-[(2-hydroxyethoxy)methyl]guanine]. By comparison, HPMPC exhibited greater activity than ACV against a thymidine kinase deficient strain of HSV 1 and was more potent than ganciclovir [DHPG, 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine] against human cytomegalovirus. In vivo, HPMPC showed exceptional potency against HSV 1 systemic infection in mice, having an ED50 of 0.1 mg/kg per day (ip) compared with 50 mg/kg per day for ACV. HPMPC was also more efficacious than ACV in the topical treatment of HSV 1 induced cutaneous lesions in guinea pigs.

  DOI：

  10.1021/jm00127a010

文献信息

• Drug. Future 1996, 21, 1003
  作者：

  DOI：——

  日期：——
• Nucleos. Nucleot. Nucl. 1989, 8, 923-926
  作者：

  DOI：——

  日期：——
• J. Med. Chem. 1989, 32, 1457-1463
  作者：

  DOI：——

  日期：——
• BRONSON, JOANNE J.;FERRARA, LOUIS M.;HOWELL, HENRY G.;BRODFUEHRER, PAUL R+, NUCLEOSIDES AND NUCLEOTIDES, 9,(1990) N, C. 746-769
  作者：BRONSON, JOANNE J.、FERRARA, LOUIS M.、HOWELL, HENRY G.、BRODFUEHRER, PAUL R+

  DOI：——

  日期：——
• WEBB, ROBERT R.;WOS, JOHN A.;BRONSON, JOANNE J.;MARTIN, JOHN C., TETRAHEDRON LETT., 29,(1988) N 43, C. 5475-5478
  作者：WEBB, ROBERT R.、WOS, JOHN A.、BRONSON, JOANNE J.、MARTIN, JOHN C.

  DOI：——

  日期：——