((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl (((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-yl)methyl) ((diethoxyphosphoryl)methyl)phosphonate | 1133431-90-9

• 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: ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl (((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-yl)methyl) ((diethoxyphosphoryl)methyl)phosphonate
• CAS: 1133431-90-9
• 化学式: C₂₆H₄₆O₁₅P₂
• 分子量: 660.59
• InChiKey: FKXLGLNTPUIMSN-BCWMSSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  43.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  154.13
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  2,3,5,6-di-O-isopropylidene-D-mannofuranose 、 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl (((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-yl)methyl) ((diethoxyphosphoryl)methyl)phosphonate 在 potassium hydride 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以45%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：

  O-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranosyl)-6-phosphorodichloridate 、 甲基膦酸二乙酯 、 甲基-2,3-O-异亚丙基-beta-D-呋喃核糖苷 在 仲丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以70%的产率得到((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl (((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyltetrahydro-5H-bis([1,3]dioxolo)[4,5-b:4',5'-d]pyran-5-yl)methyl) ((diethoxyphosphoryl)methyl)phosphonate
  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