P¹-[ethyl (1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)] P²-[ethyl (1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-yl)] methylenebis(phosphonate)

• 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: P¹-[ethyl (1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)] P²-[ethyl (1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-yl)] methylenebis(phosphonate)
• 英文别名: (1S,2R,6R,8R,9S)-8-[[[[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy-ethoxyphosphoryl]methyl-ethoxyphosphoryl]oxymethyl]-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• 化学式: C₂₆H₄₆O₁₅P₂
• 分子量: 660.59
• InChiKey: OOZMFXGVAMMFTC-JDELZWHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  154
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  ethyl (1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl) methylphosphonate 、 甲基-2,3-O-异亚丙基-beta-D-呋喃核糖苷 、 二氯磷酸乙酯 在 仲丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 30.5h， 以73%的产率得到P¹-[ethyl (1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)] P²-[ethyl (1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-yl)] methylenebis(phosphonate)
  参考文献：
  名称：

  One-Pot Carbanionic Synthesis of P¹_,P²-Diglycosyl, P¹,P¹,P²-Triglycosyl, and P¹,P¹,P²,P²-Tetraribosyl Methylenediphosphonates

  摘要：

  Novel lithiated carbanions derived from ethyl glycosyl- and diglycosyl methylphosphonates were used in a direct and convenient synthesis of P-1, P-2-diglycosyl, P-1, P-1, P-2-triglycosyl, and P-1, P-1, P-2, P-2- tetraribosyl methylenediphosphonates involving a one-pot methylidenediphosphonylation of sugars.

  DOI：

  10.1021/jo061087v

文献信息

• One-Pot Carbanionic Synthesis of <i>P</i>¹_,<i>P</i>²-Diglycosyl, <i>P</i>¹,<i>P</i>¹,<i>P</i>²-Triglycosyl, and <i>P</i>¹,<i>P</i>¹,<i>P</i>²,<i>P</i>²-Tetraribosyl Methylenediphosphonates
  作者：Claude Grison、Hicham Chibli、Nicolas Barthès、Philippe Coutrot

  DOI：10.1021/jo061087v

  日期：2006.10.1

  Novel lithiated carbanions derived from ethyl glycosyl- and diglycosyl methylphosphonates were used in a direct and convenient synthesis of P-1, P-2-diglycosyl, P-1, P-1, P-2-triglycosyl, and P-1, P-1, P-2, P-2- tetraribosyl methylenediphosphonates involving a one-pot methylidenediphosphonylation of sugars.