methyl 5-deoxy-5-C-diethoxyphosphinyl-β-D-ribofuranoside | 194412-32-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-deoxy-5-C-diethoxyphosphinyl-β-D-ribofuranoside
• 英文别名: (2S,3S,4R,5R)-2-(diethoxyphosphorylmethyl)-5-methoxyoxolane-3,4-diol
• CAS: 194412-32-3
• 化学式: C₁₀H₂₁O₇P
• 分子量: 284.246
• InChiKey: LVWFBYAOGKLXQX-ZYUZMQFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 5-deoxy-5-C-diethoxyphosphinyl-β-D-ribofuranoside 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以90%的产率得到methyl 5-deoxy-5-C-diethoxyphosphinyl-2,3-O-sulfinyl-β-D-ribofuranoside
  参考文献：
  名称：

  Synthesis of 2,3-aziridino-2,3-dideoxy-D-lyxono-γ-lactone 5-phosphonate from D-ribose, a new member of the 2,3-aziridino-γ-lactone family of synthons

  摘要：

  A formal synthesis of the novel (1S,4S,5R)-N-(benzyloxycarbonyl)-4-(diethoxyphosphinyl)methyl-3-oxa-6-azabicyclo[3.1.0]hexan-2-one 4 from D-ribose is presented. A key step involves the use of the 2,3-sulfate 12 for introduction of the C-3 azide functionality prior to aziridine ring formation. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00703-5
• 作为产物：
  描述：

  methyl 5-deoxy-5-C-(diethoxyphosphinyl)-2,3-O-isopropylidene-β-D-ribofuranoside 在 甲醇 、 碘 作用下， 反应 4.5h， 以73%的产率得到methyl 5-deoxy-5-C-diethoxyphosphinyl-β-D-ribofuranoside
  参考文献：
  名称：

  Synthesis of 2,3-aziridino-2,3-dideoxy-D-lyxono-γ-lactone 5-phosphonate from D-ribose, a new member of the 2,3-aziridino-γ-lactone family of synthons

  摘要：

  A formal synthesis of the novel (1S,4S,5R)-N-(benzyloxycarbonyl)-4-(diethoxyphosphinyl)methyl-3-oxa-6-azabicyclo[3.1.0]hexan-2-one 4 from D-ribose is presented. A key step involves the use of the 2,3-sulfate 12 for introduction of the C-3 azide functionality prior to aziridine ring formation. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00703-5

文献信息

• Synthesis of 2,3-aziridino-2,3-dideoxy-D-lyxono-γ-lactone 5-phosphonate from D-ribose, a new member of the 2,3-aziridino-γ-lactone family of synthons
  作者：Philippe Dauban、Bernhard Hofmann、Robert H. Dodd

  DOI：10.1016/s0040-4020(97)00703-5

  日期：1997.8

  A formal synthesis of the novel (1S,4S,5R)-N-(benzyloxycarbonyl)-4-(diethoxyphosphinyl)methyl-3-oxa-6-azabicyclo[3.1.0]hexan-2-one 4 from D-ribose is presented. A key step involves the use of the 2,3-sulfate 12 for introduction of the C-3 azide functionality prior to aziridine ring formation. (C) 1997 Elsevier Science Ltd.