4-amino-2-(2'-deoxy-β-D-erythro-pentafuranosyl)-2H-pyrazolo<3,4-d>pyrimidine | 99272-48-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 4-amino-2-(2'-deoxy-β-D-erythro-pentafuranosyl)-2H-pyrazolo<3,4-d>pyrimidine
• 英文别名: 4-amino-2-(2-deoxy-β-D-erythro-pentofuranosyl)-2H-pyrazolo<3,4-d>pyrimidine；8-aza-7-deaza-2'-deoxyadenosine, N⁸-linked；N⁸c⁷z⁸A_d；4-amino-2-(2-deoxy-β-D-erythro-pentofuranosyl)-2H-pyrazolo[3,4-d]pyrimidine；(2R,3S,5R)-5-(4-aminopyrazolo[3,4-d]pyrimidin-2-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 99272-48-7
• 化学式: C₁₀H₁₃N₅O₃
• 分子量: 251.245
• InChiKey: RWOPHLREWURYIP-XLPZGREQSA-N

物化性质

• 熔点：
  198 °C
• 沸点：
  633.5±55.0 °C(predicted)
• 密度：
  1.91±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-amino-2-(2'-deoxy-β-D-erythro-pentafuranosyl)-2H-pyrazolo<3,4-d>pyrimidine 生成 N-[2-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-[[di(propan-2-yl)amino]-methoxyphosphanyl]oxyoxolan-2-yl]pyrazolo[3,4-d]pyrimidin-4-yl]benzamide
  参考文献：
  名称：

  SEELA, F.;DRILLER, H.;KAISER, K.;ROSEMEYER, H.;STEKER, H., NUCLEOSIDES AND NUCLEOTIDES, 8,(1989) N-6, C. 789-792

  摘要：

  DOI：
• 作为产物：
  描述：

  1-Α-氯-3,5-二-O-对甲苯甲酰基-2-脱氧-D-呋喃核糖 在 四丁基硫酸氢铵 ammonium hydroxide 、 sodium hydroxide 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 76.02h， 生成 4-amino-2-(2'-deoxy-β-D-erythro-pentafuranosyl)-2H-pyrazolo<3,4-d>pyrimidine
  参考文献：
  名称：

  通过相转移糖基化轻松合成别嘌醇和4-氨基-1 H-吡唑并[3,4- d ]嘧啶的2'-脱氧呋喃核苷

  摘要：

  4-甲氧基-1 H-吡唑并[3,4- d ]嘧啶与2-脱氧呋喃呋喃糖基氯9的相转移糖基化反应形成N（1）-β-核苷10a为主要产物（39％）。作为副产物，分离出α-D-异构体11a（7％）和N（2）-异构体12a（18％）。这些异构体的分配基于其1 H-和13 C-NMR光谱进行。除去糖保护基团分别得到4-甲氧基核苷10b，11b和12b。4-MeO-基团的亲核取代产生别嘌呤醇的2-脱氧核糖呋喃糖苷1-4和4-氨基-1H-吡唑并[3，4- d ]嘧啶。

  DOI：

  10.1002/hlca.19850680305

文献信息

• Facile Synthesis of 2?-Deoxyribofuranosides of Allopurinol and 4-Amino-1H-pyrazolo[3,4-d]pyrimidinevia Phase-Transfer Glycosylation
  作者：Frank Seela、Herbert Steker

  DOI：10.1002/hlca.19850680305

  日期：1985.5.15

  Phase-transfer glycosylation of 4-methoxy-1H-pyrazolo[3,4-d]pyrimidine with the 2-deoxyribofuranosyl chloride 9 formed the N(1)-β-nucleoside 10a as main product (39%). As by-products the α-D-anomer 11a (7%) and the N(2)-isomer 12a (18%) were isolated. Assignment of these isomers was made on the basis of their 1H- and 13C-NMR spectra. Removal of the sugar-protecting groups yielded the 4-methoxy-nucleosides

  4-甲氧基-1 H-吡唑并[3,4- d ]嘧啶与2-脱氧呋喃呋喃糖基氯9的相转移糖基化反应形成N（1）-β-核苷10a为主要产物（39％）。作为副产物，分离出α-D-异构体11a（7％）和N（2）-异构体12a（18％）。这些异构体的分配基于其1 H-和13 C-NMR光谱进行。除去糖保护基团分别得到4-甲氧基核苷10b，11b和12b。4-MeO-基团的亲核取代产生别嘌呤醇的2-脱氧核糖呋喃糖苷1-4和4-氨基-1H-吡唑并[3，4- d ]嘧啶。
• N8- and C8- linked purine bases as universal nucleosides used for oligonucleotide hybridization
  申请人：Roche Diagnostics GmbH

  公开号：EP1138688A1

  公开（公告）日：2001-10-04

  The present invention is directed to a nucleic acid binding compound comprising N8- or C8-linked purine bases or structurally related heterocycles, a compound useful for the preparation of such compound, a binding product of this nucleic acid binding compound with a nucleic acid, a method for the determination of a nucleic acid using said compound, and several uses of 8-linked purine bases and structurally related heterocycles. Compounds according to the present invention have advantageous properties when used in hybridization methods.

  本发明涉及一种核酸结合化合物，该化合物包含 N8-或 C8-连接的嘌呤碱基或结构相关的杂环，一种用于制备这种化合物的化合物，这种核酸结合化合物与核酸的结合产物，一种使用所述化合物测定核酸的方法，以及 8-连接的嘌呤碱基和结构相关的杂环的几种用途。根据本发明的化合物在杂交方法中使用时具有优势特性。
• N8- and C8-linked purine bases as universal nucleosides used for oligonucleotide hybridization
  申请人：Roche Diagnostics GmbH

  公开号：EP1138689A1

  公开（公告）日：2001-10-04

  The present invention is directed to a nucleic acid binding compound comprising N8- or C8-linked purine bases or structurally related heterocycles, a compound useful for the preparation of such compound, a binding product of this nucleic acid binding compound with a nucleic acid, a method for the determination of a nucleic acid using said compound, and several uses of 8-linked purine bases and structurally related heterocycles. Compounds according to the present invention have advantageous properties when used in hybridization methods.

  本发明涉及一种核酸结合化合物，该化合物包含 N8-或 C8-连接的嘌呤碱基或结构相关的杂环，一种用于制备这种化合物的化合物，这种核酸结合化合物与核酸的结合产物，一种使用所述化合物测定核酸的方法，以及 8-连接的嘌呤碱基和结构相关的杂环的几种用途。根据本发明的化合物在杂交方法中使用时具有优势特性。
• Base-Pairing Properties of 8-Aza-7-deazaadenine Linked via the 8-Position to the DNA Backbone
  作者：Frank Seela、Matthias Zulauf、Harald Debelak

  DOI：10.1002/1522-2675(20000705)83:7<1437::aid-hlca1437>3.0.co;2-u

  日期：2000.7.5

  The base-pairing properties of oligonucleotides containing the unusual N-8-linked 8-aza-7-deazaadenine 2'-deoxyribonucleoside (2a) as well as its 7-bromo derivative 2b are described. The oligonucleotides were prepared by solid-phase synthesis employing phosphoramidite chemistry. Compound 2a forms a strong base pair with T-d for which a reverse Watson-Crick pair is suggested (Fig. 9). Compound 2a displays a lower N-glycosylic-bond stability than its Ng-nucleoside and shows strong stacking interactions when incorporated into oligonucleotides. The replacement of 2'-deoxyadenosine by 2a does not significantly influence the duplex stability. However, this behavior depends on the position of the incorporation.
• SEELA, F.;DRILLER, H.;KAISER, K.;ROSEMEYER, H.;STEKER, H., NUCLEOSIDES AND NUCLEOTIDES, 8,(1989) N-6, C. 789-792
  作者：SEELA, F.、DRILLER, H.、KAISER, K.、ROSEMEYER, H.、STEKER, H.

  DOI：——

  日期：——