(-)-β-D-carbocyclic-1'-(9H-hypoxanthin-9-yl)-2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl) ribonucleoside | 250699-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (-)-β-D-carbocyclic-1'-(9H-hypoxanthin-9-yl)-2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl) ribonucleoside
• 英文别名: 9-[(3aS,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]-1H-purin-6-one
• CAS: 250699-06-0
• 化学式: C₂₀H₃₂N₄O₄Si
• 分子量: 420.584
• InChiKey: KXQBATZMEQYGFX-XOUADPBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  87
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-β-D-carbocyclic-1'-(9H-hypoxanthin-9-yl)-2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl) ribonucleoside 在 四氮唑 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 (-)-β-D-carbocyclic-1'-(9H-hypoxanthin-9-yl)-2',3'-O-isopropylidene-5'-O-(o-xylylenephosphite) ribonucleoside
  参考文献：
  名称：

  Synthesis of Chiral Carbocyclic Ribonucleotides

  摘要：

  The carbocyclic analogs of CMP, UMP, GMP, IMP, and ribo-TMP, of the same absolute configuration as the naturally occurring beta-D-ribofuranose-based ribonucleoside monophosphates, have been synthesized. The synthetic route employed Mitsunobu coupling of the heterocycles, appropriately protected where necessary, with a differentially protected, chiral carbocyclic core.

  DOI：

  10.1080/07328319908044853
• 作为产物：
  描述：

  次黄嘌呤 、 (1S,2S,3R,4S)-4-t-butyldimethylsiloxymethyl-2,3-isopropylidenedioxycyclopentanol 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 以31.7%的产率得到(-)-β-D-carbocyclic-1'-(9H-hypoxanthin-9-yl)-2',3'-O-isopropylidene-5'-O-(tert-butyldimethylsilyl) ribonucleoside
  参考文献：
  名称：

  Synthesis of Chiral Carbocyclic Ribonucleotides

  摘要：

  The carbocyclic analogs of CMP, UMP, GMP, IMP, and ribo-TMP, of the same absolute configuration as the naturally occurring beta-D-ribofuranose-based ribonucleoside monophosphates, have been synthesized. The synthetic route employed Mitsunobu coupling of the heterocycles, appropriately protected where necessary, with a differentially protected, chiral carbocyclic core.

  DOI：

  10.1080/07328319908044853