3'-O-levulinyl-2'-O-methoxyethyl-N²-isobutyrylguanosine | 440327-62-8

• 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: 3'-O-levulinyl-2'-O-methoxyethyl-N²-isobutyrylguanosine
• 英文别名: N-isobutyryl-3'-O-levulinyl-2'-O-(2-methoxyethyl)guanosine；[(2R,3R,4R,5R)-2-(hydroxymethyl)-4-(2-methoxyethoxy)-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]oxolan-3-yl] 4-oxopentanoate
• CAS: 440327-62-8
• 化学式: C₂₂H₃₁N₅O₉
• 分子量: 509.516
• InChiKey: WUQCWEPMNWVMIW-TXRZWFJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  180
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3'-O-levulinyl-2'-O-methoxyethyl-N²-isobutyrylguanosine 在 四氮唑 、 diethyldithiocarbonate disulfide 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  2-Methyl-5-tert-butylthiophenol—An Odorless Deprotecting Reagent Useful in Synthesis of Oligonucleotides and Their Analogs

  摘要：

  A solution of 2-methyl-5-tert-butylthiophenol and triethylamine in acetonitrile efficiently removed the methyl protecting groups from phosphate and phosphorothioate triesters and yielded oligonucleotides of high quality. This inexpensive odorless liquid is not toxic and is a suitable replacement for hazardous thiophenol and other reagents often used for this purpose.graphics.

  DOI：

  10.1081/ncn-120022038
• 作为产物：
  描述：

  N-(9-(((2R,3R,4R,5R)-4-)羟基-5-(羟甲基)-3-(2-甲氧基乙氧基)四氢呋喃-2-基)-6-氧代-6,9-二氢-1H-嘌呤-2-基)异丁酰胺 在 4-二甲氨基吡啶 、 Candida antarctica lipase B 、 phosphate buffer 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 26.0h， 生成 3'-O-levulinyl-2'-O-methoxyethyl-N²-isobutyrylguanosine
  参考文献：
  名称：

  寡核苷酸溶液相合成的基本组成部分：使用酶促方法对3'，5'-Di-O-乙酰丙氨酰核苷进行区域选择性水解。

  摘要：

  通过区域选择性酶水解反应，由相应的3'，5'-二-O-乙酰丙酰衍生物开发了一种简便的3'-和5'-O-乙酰丙酰-2'-脱氧核苷合成方法，避免了一些繁琐的化学保护/脱保护步骤。因此，发现南极假丝酵母脂肪酶B（CAL-B）选择性地水解5'-乙酰丙酸酯，以> 80％的分离产率提供3'-O-乙酰丙酰-2'-脱氧核苷3。另一方面，固定化的假单胞菌洋葱脂肪酶（PSL-C）和南极假丝酵母脂肪酶A（CAL-A）在3'-位置对水解表现出相反的选择性，从而在> 70的情况下提供5'-O-乙酰丙酰衍生物4 ％产率。相似的水解过程已成功扩展到3'-和5'-O-乙酰丙氨酰保护的2'的合成 -O-烷基核糖核苷7和8。这项工作首次证明了商业CAL-B和PSL-C在乙酰丙酸酯的区域选择性水解方面具有优异的选择性和产率。值得注意的是，受保护的胞苷和腺苷碱衍生物不足以用作用CAL-B进行酶促水解的底物，而PSL-C能够在选择

  DOI：

  10.1021/jo020080k

文献信息

• Novel enzymatic synthesis of levulinyl protected nucleosides useful for solution phase synthesis of oligonucleotides
  作者：Javier Garcı́a、Susana Fernández、Miguel Ferrero、Yogesh S. Sanghvi、Vicente Gotor

  DOI：10.1016/j.tetasy.2003.07.009

  日期：2003.11

  An efficient synthesis of 3' and 5'-O-levulinyl-2'-deoxy- and 2'-O-alkylribonucleosides has been developed front appropriate nucleosides by enzyme-catalyzed regioselective acylation in organic solvents. Several lipases were screened in combination with acetonoxime levulinate as an acylating agent. Immobilized Pseudomonas cepacia lipase (PSL-C) was selected for acylation of the 3'-hydroxyl group in nucleosides, furnishing 3'-O-levulinylated products 1 and 3 in excellent yields. Similarly, Candida antarctica lipase B (CAL-B) provided 5'-O-levulinyl nucleosides 2 and 4 in high yields. Base-protected cytidine and adenosine analogs were found to be good substrates for lipase-mediated acylations. To demonstrate the industrial utility of this method, 3'-O-levulinyl thymidine and N-2-Ibu-5'-O-levulinyl-2'deoxygunaosine were synthesized on a 25 g scale. Additionally, PSL-C was reused to make the processes further economical. (C) 2003 Elsevier Ltd. All rights reserved.
• Building Blocks for the Solution Phase Synthesis of Oligonucleotides:  Regioselective Hydrolysis of 3‘,5‘-Di-<i>O</i>-levulinylnucleosides Using an Enzymatic Approach
  作者：Javier García、Susana Fernández、Miguel Ferrero、Yogesh S. Sanghvi、Vicente Gotor

  DOI：10.1021/jo020080k

  日期：2002.6.1

  opposite selectivity toward the hydrolysis at the 3'-position, affording 5'-O-levulinyl derivatives 4 in >70% yields. A similar hydrolysis procedure was successfully extended to the synthesis of 3'- and 5'-O-levulinyl-protected 2'-O-alkylribonucleosides 7 and 8. This work demonstrates for the first time application of commercial CAL-B and PSL-C toward regioselective hydrolysis of levulinyl esters with excellent

  通过区域选择性酶水解反应，由相应的3'，5'-二-O-乙酰丙酰衍生物开发了一种简便的3'-和5'-O-乙酰丙酰-2'-脱氧核苷合成方法，避免了一些繁琐的化学保护/脱保护步骤。因此，发现南极假丝酵母脂肪酶B（CAL-B）选择性地水解5'-乙酰丙酸酯，以> 80％的分离产率提供3'-O-乙酰丙酰-2'-脱氧核苷3。另一方面，固定化的假单胞菌洋葱脂肪酶（PSL-C）和南极假丝酵母脂肪酶A（CAL-A）在3'-位置对水解表现出相反的选择性，从而在> 70的情况下提供5'-O-乙酰丙酰衍生物4 ％产率。相似的水解过程已成功扩展到3'-和5'-O-乙酰丙氨酰保护的2'的合成 -O-烷基核糖核苷7和8。这项工作首次证明了商业CAL-B和PSL-C在乙酰丙酸酯的区域选择性水解方面具有优异的选择性和产率。值得注意的是，受保护的胞苷和腺苷碱衍生物不足以用作用CAL-B进行酶促水解的底物，而PSL-C能够在选择
• 2-Methyl-5-<i>tert</i>-butylthiophenol—An Odorless Deprotecting Reagent Useful in Synthesis of Oligonucleotides and Their Analogs
  作者：R. Krishna Kumar、Douglas L. Cole、Vasulinga T. Ravikumar

  DOI：10.1081/ncn-120022038

  日期：2003.7.1

  A solution of 2-methyl-5-tert-butylthiophenol and triethylamine in acetonitrile efficiently removed the methyl protecting groups from phosphate and phosphorothioate triesters and yielded oligonucleotides of high quality. This inexpensive odorless liquid is not toxic and is a suitable replacement for hazardous thiophenol and other reagents often used for this purpose.graphics.