N6-(hex-5-ynyl)-5'-(2-hydroxyethyl)-5'-deoxy-2',3'-bis(O-isopropylidene)adenosine | 1616876-16-4

• 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: N6-(hex-5-ynyl)-5'-(2-hydroxyethyl)-5'-deoxy-2',3'-bis(O-isopropylidene)adenosine
• 英文别名: 2-[[(3aR,4R,6R,6aR)-4-[6-(hex-5-ynylamino)purin-9-yl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methylamino]ethanol
• CAS: 1616876-16-4
• 化学式: C₂₁H₃₀N₆O₄
• 分子量: 430.507
• InChiKey: JAYCQQVLVMWSIF-WVSUBDOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N6-(hex-5-ynyl)-5'-(2-hydroxyethyl)-5'-deoxy-2',3'-bis(O-isopropylidene)adenosine 在 咪唑 、 盐酸 、 碘 、 sodium cyanoborohydride 、 溶剂黄146 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis and evaluation of N6-substituted azide- and alkyne-bearing N-mustard analogs of S-adenosyl-l-methionine

  摘要：

  The synthesis of a family of N-mustard analogs of S-adenosyl-L-methionine (SAM) containing azides and alkynes at the N6-position of the adenosine base has been accomplished from commercially available inosine. Further biochemical analysis of these analogs indicates successful modification of pUC19 plasmid DNA in an enzyme-dependent fashion with DNA methyltransferases M.TaqI and M.Hhal. (C) 2014 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2014.05.055
• 作为产物：
  描述：

  2',3'-O-异丙叉肌苷 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 73.0h， 生成 N6-(hex-5-ynyl)-5'-(2-hydroxyethyl)-5'-deoxy-2',3'-bis(O-isopropylidene)adenosine
  参考文献：
  名称：

  Synthesis and evaluation of N6-substituted azide- and alkyne-bearing N-mustard analogs of S-adenosyl-l-methionine

  摘要：

  The synthesis of a family of N-mustard analogs of S-adenosyl-L-methionine (SAM) containing azides and alkynes at the N6-position of the adenosine base has been accomplished from commercially available inosine. Further biochemical analysis of these analogs indicates successful modification of pUC19 plasmid DNA in an enzyme-dependent fashion with DNA methyltransferases M.TaqI and M.Hhal. (C) 2014 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2014.05.055

文献信息

• Synthesis and evaluation of N6-substituted azide- and alkyne-bearing N-mustard analogs of S-adenosyl-l-methionine
  作者：Mohamed Ramadan、Natalie K. Bremner-Hay、Steig A. Carlson、Lindsay R. Comstock

  DOI：10.1016/j.tet.2014.05.055

  日期：2014.8

  The synthesis of a family of N-mustard analogs of S-adenosyl-L-methionine (SAM) containing azides and alkynes at the N6-position of the adenosine base has been accomplished from commercially available inosine. Further biochemical analysis of these analogs indicates successful modification of pUC19 plasmid DNA in an enzyme-dependent fashion with DNA methyltransferases M.TaqI and M.Hhal. (C) 2014 The Authors. Published by Elsevier Ltd.