O⁶-(2-furylmethyl)-3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxyguanosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: O⁶-(2-furylmethyl)-3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxyguanosine
• 英文别名: 9-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-6-(furan-2-ylmethoxy)purin-2-amine
• 化学式: C₂₇H₄₅N₅O₅Si₂
• 分子量: 575.856
• InChiKey: JBEYBYORFJWDLS-PWRODBHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.28
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  糠醇 、 3',5'-bis-O-(tert-butyldimethylsilyl)-O⁶-[(2,4,6-trimethylphenyl)sulfonyl]-2'-deoxyguanosine 在 三乙烯二胺 、 4 A molecular sieve 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙二醇二甲醚 为溶剂， 反应 24.5h， 以79%的产率得到O⁶-(2-furylmethyl)-3',5'-bis(O-tert-butyldimethylsilyl)-2'-deoxyguanosine
  参考文献：
  名称：

  Facile Synthesis of O⁶-Alkyl-, O⁶-Aryl-, and Diaminopurine Nucleosides from 2‘-Deoxyguanosine

  摘要：

  [GRAPHICS]The 3',5'-bis-O-TBDMS derivative of 2'-deoxyguanosine can be converted to its O-6-alkyl and O-6-aryl ethers as well as to N-6-substituted diaminopurine nucleosides in two simple steps. Also described is a novel, nonaqueous, one-step O-6-desulfonylation method that leads to deprotection of the carbonyl moiety of 2'-deoxyguanosine.

  DOI：

  10.1021/ol005564m

文献信息

• Facile Synthesis of <i>O</i>⁶-Alkyl-, <i>O</i>⁶-Aryl-, and Diaminopurine Nucleosides from 2‘-Deoxyguanosine
  作者：Mahesh K. Lakshman、Felix N. Ngassa、John C. Keeler、Yen Q. V. Dinh、John H. Hilmer、Larry M. Russon

  DOI：10.1021/ol005564m

  日期：2000.4.1

  [GRAPHICS]The 3',5'-bis-O-TBDMS derivative of 2'-deoxyguanosine can be converted to its O-6-alkyl and O-6-aryl ethers as well as to N-6-substituted diaminopurine nucleosides in two simple steps. Also described is a novel, nonaqueous, one-step O-6-desulfonylation method that leads to deprotection of the carbonyl moiety of 2'-deoxyguanosine.