O-ethyl O'-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranosyl)[(diethoxyphosphinyl)methyl]phosphonate | 898822-97-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: O-ethyl O'-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranosyl)[(diethoxyphosphinyl)methyl]phosphonate
• 英文别名: (1S,2R,6R,8R,9S)-8-[[diethoxyphosphorylmethyl(ethoxy)phosphoryl]oxymethyl]-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• CAS: 898822-97-4
• 化学式: C₁₉H₃₆O₁₁P₂
• 分子量: 502.436
• InChiKey: FDIUWFHYUFVVEP-ISROEKCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  O-ethyl O'-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranosyl)[(diethoxyphosphinyl)methyl]phosphonate 、 (3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde 在 potassium hydride 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以58%的产率得到
  参考文献：
  名称：

  Concise Synthesis ofP-Glycosyl Alkenylphosphonates andP,C-di andP,P,Ctri-Glycosyl Phosphonates

  摘要：

  A direct access to P-glycosyl-, P, P-di-glycosyl alkenylphosphonates and P, C-glycosyl phosphonates is described. The method involves the Horner reaction of an anion derived from P-monoglycosyl and P1, P'-diglycosyl methylenediphosphonates either on the exocyclic aldehyde group of carbohydrates or on the masked aldehydic form of the furanose hemiacetals. In this last case, the carbonyl olefination, followed by an intramolecular cyclization, leads to P,C-di and P,P,C-triglycosyl phosphonates.

  DOI：

  10.1080/07328300802638472
• 作为产物：
  描述：

  甲基膦酸二乙酯 、 二氯磷酸乙酯 、 双丙酮半乳糖 在 仲丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.33h， 以80%的产率得到O-ethyl O'-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranosyl)[(diethoxyphosphinyl)methyl]phosphonate
  参考文献：
  名称：

  Monoglycosyl, diglycosyl, and dinucleoside methylenediphosphonates: direct synthesis and antiviral activity

  摘要：

  A direct and general access to D-glycosyl 3-, 5-, or 6-methylenediphosphonates, di-D-glycosyl 1,5-, 3,5-, 3,6-, 5,5-, or 6,6-methylenediphosphonates and dithymidine 3',5'-methylenediphosphonate is described. The method involves the one-pot alkylidenediphosphorylation of glycosyl or thymidine derivatives. No antiviral activity was detected against a panel of RNA and DNA viruses. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.023

文献信息

• Monoglycosyl, diglycosyl, and dinucleoside methylenediphosphonates: direct synthesis and antiviral activity
  作者：Claude Grison、Stéphane Joliez、E. De Clercq、Philippe Coutrot

  DOI：10.1016/j.carres.2006.03.023

  日期：2006.7

  A direct and general access to D-glycosyl 3-, 5-, or 6-methylenediphosphonates, di-D-glycosyl 1,5-, 3,5-, 3,6-, 5,5-, or 6,6-methylenediphosphonates and dithymidine 3',5'-methylenediphosphonate is described. The method involves the one-pot alkylidenediphosphorylation of glycosyl or thymidine derivatives. No antiviral activity was detected against a panel of RNA and DNA viruses. (c) 2006 Elsevier Ltd. All rights reserved.
• Concise Synthesis of<i>P</i>-Glycosyl Alkenylphosphonates and<i>P,C</i>-di and<i>P,P,C</i>tri-Glycosyl Phosphonates
  作者：Claude Grison、Hicham Chibli

  DOI：10.1080/07328300802638472

  日期：2009.1.30

  A direct access to P-glycosyl-, P, P-di-glycosyl alkenylphosphonates and P, C-glycosyl phosphonates is described. The method involves the Horner reaction of an anion derived from P-monoglycosyl and P1, P'-diglycosyl methylenediphosphonates either on the exocyclic aldehyde group of carbohydrates or on the masked aldehydic form of the furanose hemiacetals. In this last case, the carbonyl olefination, followed by an intramolecular cyclization, leads to P,C-di and P,P,C-triglycosyl phosphonates.