1'-(adenin-9-yl)-2',3'-O-(isopropylidene)-D-ribofuranurononitrile | 54918-23-9

• 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: 1'-(adenin-9-yl)-2',3'-O-(isopropylidene)-D-ribofuranurononitrile
• 英文别名: O^2'_,O3'-isopropylidene-5'-nitrilo-5'-deoxy-adenosine；1-(6-amino-purin-9-yl)-O²,O³-isopropylidene-β-D-ribofuranurononitrile；beta-D-Ribofuranurononitrile, 1-(6-amino-9H-purin-9-yl)-1-deoxy-2,3-O-(1-methylethylidene)-；(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carbonitrile
• CAS: 54918-23-9
• 化学式: C₁₃H₁₄N₆O₃
• 分子量: 302.293
• InChiKey: JVGCNJIUIZZKAC-WOUKDFQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1'-(adenin-9-yl)-2',3'-O-(isopropylidene)-D-ribofuranurononitrile 生成 (4R)-1-(6-amino-purin-9-yl)-4-(1(2)H-tetrazol-5-yl)-β-D-1-deoxy-erythrofuranose
  参考文献：
  名称：

  5′-substituted-5′-deoxy nucleosides

  摘要：

  DOI：

  10.1016/s0040-4020(01)97469-1
• 作为产物：
  描述：

  (3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde oxime 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以95%的产率得到1'-(adenin-9-yl)-2',3'-O-(isopropylidene)-D-ribofuranurononitrile
  参考文献：
  名称：

  A Simple Synthesis of Nitriles from Aldoximes

  摘要：

  [GRAPHICS]Easily synthesized aldoximes have been converted to the corresponding nitriles under very mild conditions by a simple reaction with 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) and DBU in CH2Cl2, THF, or DMF. As an alternative reagent that eliminates the formation of hexamethylphosphoramide as a byproduct, use of 1H-benzotriazol-1-yl-4-methylbenzenesulfonate (Bt-OTs) and DBU was investigated. Reactions with this reagent also proceeded smoothly and in good yields, although in one case N-sulfonylation was observed. An attempt to gain mechanistic insight into the BOP-mediated reaction has been made using (31)p{H-1} NMR. However, no phosphorus-bearing intermediate could be readily observed. Finally, the method has been applied to the synthesis of an antiviral 4'-cyano adenosine analogue from a commercial precursor using a single saccharide protecting group.

  DOI：

  10.1021/jo900100v

文献信息

• A Simple Synthesis of Nitriles from Aldoximes
  作者：Manish K. Singh、Mahesh K. Lakshman

  DOI：10.1021/jo900100v

  日期：2009.4.17

  [GRAPHICS]Easily synthesized aldoximes have been converted to the corresponding nitriles under very mild conditions by a simple reaction with 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) and DBU in CH2Cl2, THF, or DMF. As an alternative reagent that eliminates the formation of hexamethylphosphoramide as a byproduct, use of 1H-benzotriazol-1-yl-4-methylbenzenesulfonate (Bt-OTs) and DBU was investigated. Reactions with this reagent also proceeded smoothly and in good yields, although in one case N-sulfonylation was observed. An attempt to gain mechanistic insight into the BOP-mediated reaction has been made using (31)pH-1} NMR. However, no phosphorus-bearing intermediate could be readily observed. Finally, the method has been applied to the synthesis of an antiviral 4'-cyano adenosine analogue from a commercial precursor using a single saccharide protecting group.
• 5′-substituted-5′-deoxy nucleosides
  作者：J.J. Baker、A.M. Mian、J.R. Tittensor

  DOI：10.1016/s0040-4020(01)97469-1

  日期：1974.1