5'-deoxy-5'-[N-(tert-butyldimethylsilyloxy)-N-(p-toluenesulfonyl)amino]-2',3'-O-(isopropylidene)adenosine | 1142935-23-6

• 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: 5'-deoxy-5'-[N-(tert-butyldimethylsilyloxy)-N-(p-toluenesulfonyl)amino]-2',3'-O-(isopropylidene)adenosine
• 英文别名: N-[[(3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl]-N-[tert-butyl(dimethyl)silyl]oxy-4-methylbenzenesulfonamide
• CAS: 1142935-23-6
• 化学式: C₂₆H₃₈N₆O₆SSi
• 分子量: 590.776
• InChiKey: JXEZRKWZGWMEKG-UMCMBGNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5'-deoxy-5'-[N-(tert-butyldimethylsilyloxy)-N-(p-toluenesulfonyl)amino]-2',3'-O-(isopropylidene)adenosine 在 cesium fluoride 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以80%的产率得到(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde oxime
  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
• 作为产物：
  描述：

  O-(叔丁基二甲基硅基)-N-甲苯磺酰基羟胺 、 2',3'-异丙叉腺苷 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以81%的产率得到5'-deoxy-5'-[N-(tert-butyldimethylsilyloxy)-N-(p-toluenesulfonyl)amino]-2',3'-O-(isopropylidene)adenosine
  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