O-(1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-5-phosphorodichloridate | 87372-46-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-5-phosphorodichloridate
• CAS: 87372-46-1
• 化学式: C₉H₁₅Cl₂O₆P
• 分子量: 321.094
• InChiKey: BTASJEQTUYHANU-WCTZXXKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  O-(1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-5-phosphorodichloridate 以 水 为溶剂， 生成 D-ribose 5-phosphate
  参考文献：
  名称：

  Practical synthesis of 5-phospho-D-ribosyl .alpha.-1-pyrophosphate (PRPP): enzymatic routes from ribose 5-phosphate or ribose

  摘要：

  DOI：

  10.1021/ja00363a037
• 作为产物：
  描述：

  甲基-2,3-O-异亚丙基-beta-D-呋喃核糖苷 在 三乙胺 、 三氯氧磷 作用下， 以 乙醚 为溶剂， 生成 O-(1-O-methyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-5-phosphorodichloridate
  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

• Lithiated alkylidenebis(phosphonates): Reactive phosphorus intermediates in the synthesis of 3‐amino‐1‐alkenylphosphonates
  作者：Claude Grison、Tomasz Krzysztof Olszewski

  DOI：10.1002/hc.20450

  日期：2008.7

  An efficient and stereoselective-synthesis of 3-amino-1-alkenylphosphonates by a direct procedure involving alkylidene diphosphorylation of nucleophiles followed by a Horner--Emmons olefination of aminoaldehydes is reported. The versatility of the method is illustrated by the preparation of P-monoglycosyl-, P-diglycosyl 3-aminoalkenyl-, and alkylphosphonates. © 2008 Wiley Periodicals, Inc. Heteroatom

  3-氨基-1-链烯基膦酸酯的有效和立体选择性合成通过直接程序涉及亲核试剂的亚烷基二磷酸化，然后是氨基醛的霍纳-埃蒙斯烯化。该方法的多功能性通过制备 P-单糖基-、P-二糖基 3-氨基烯基-和烷基膦酸盐来说明。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:461–469, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20450
• 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.