bis(1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-yl) methylphosphonate | 866478-82-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: bis(1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-yl) methylphosphonate
• 英文别名: (3aR,4R,6R,6aR)-6-[[[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy-methyl-oxidophosphaniumyl]oxymethyl]-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
• CAS: 866478-82-2
• 化学式: C₁₉H₃₃O₁₁P
• 分子量: 468.438
• InChiKey: RSXBVIRYNPHLNF-ZRXGBZJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  bis(1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-yl) methylphosphonate 、 甲基-2,3-O-异亚丙基-beta-D-呋喃核糖苷 、 O-(1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-5-phosphorodichloridate 在 仲丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以30%的产率得到P¹,P²-tetrakis(1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-yl) methylenediphosphonate
  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
• 作为产物：
  描述：

  甲基膦酞二氯 、 甲基-2,3-O-异亚丙基-beta-D-呋喃核糖苷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以90%的产率得到bis(1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranos-5-yl) methylphosphonate
  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 access to methylenebis(phosphonate) analogues of natural P1,P2-glycosyl-disubstituted pyrophosphates
  作者：Claude Grison、Christophe Letondor、Hicham Chibli、Philippe Coutrot

  DOI：10.1016/j.tetlet.2005.07.076

  日期：2005.9

  Two novel lithiated carbanions derived from ethyl (1,2:3,4-diisopropylidene-α-d-galactopyranosyl) methyl phosphonate 3a and ethyl (1-O-methyl-2,3-O-isopropylidene-β-d-ribofuranosyl) methylphosphonate 3b were used in the one-pot alkylidene diphosphorylation of 2,3-O-isopropylidene uridine or 2,3:5,6-di-O-isopropylidene-d-mannofuranose to synthesise the methylenebis(phosphonate) analogues of natural

  衍生自乙基（1,2：3,4-二异亚丙基-α-d-半乳糖吡喃基）甲基膦酸酯3a和乙基（1 - O-甲基-2,3- O-异亚丙基-β-d-核糖）的两种新型锂化碳负离子呋喃糖基）甲基膦3B是在的一锅亚烷基diphosphorylation使用2,3- Ò异亚丙基尿苷或2,3：5,6-二- ö异亚丙基d-mannofuranose以合成的天然的亚甲基双（膦酸盐）类似物P 1，P 2-糖基二取代的焦磷酸盐。
• 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.