((2S,5R)-5-(6-Amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl benzoate | 117174-29-5

• 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: ((2S,5R)-5-(6-Amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl benzoate
• 英文别名: [(2S,5R)-5-(6-aminopurin-9-yl)oxolan-2-yl]methyl benzoate
• CAS: 117174-29-5
• 化学式: C₁₇H₁₇N₅O₃
• 分子量: 339.354
• InChiKey: HNESBGWMHRLOIO-QWHCGFSZSA-N

物化性质

• 沸点：
  590.9±60.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ((2S,5R)-5-(6-Amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl benzoate 在 氨 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以94%的产率得到2',3'-双脱氧腺苷
  参考文献：
  名称：

  ADA-Bypass by lipophilic cycloSal-ddAMP pro-nucleotides A second example of the efficiency of the cycloSal-Concept

  摘要：

  The synthesis of lipophilic pro-nucleotides of ddAMP 2 based on cycloSal-ddAMP 3a-c is described. Phosphotriesters 3 released ddAMP 2 selectively by a controlled, chemically induced tandem reaction. CycloSal-phosphotriesters 3 exhibited antiviral activity against HIV-1/HIV-2 in CEM cells that where by a factor up to hundred higher as compared to ddA 1. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00265-5
• 作为产物：
  描述：

  2'-脱氧腺苷 在 N,N'-bis[2-oxo-3-oxazolidinyl]-phosphorodiamidic chloride 、 Barton reagent 作用下， 以 吡啶 为溶剂， 生成 ((2S,5R)-5-(6-Amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methyl benzoate
  参考文献：
  名称：

  ADA-Bypass by lipophilic cycloSal-ddAMP pro-nucleotides A second example of the efficiency of the cycloSal-Concept

  摘要：

  The synthesis of lipophilic pro-nucleotides of ddAMP 2 based on cycloSal-ddAMP 3a-c is described. Phosphotriesters 3 released ddAMP 2 selectively by a controlled, chemically induced tandem reaction. CycloSal-phosphotriesters 3 exhibited antiviral activity against HIV-1/HIV-2 in CEM cells that where by a factor up to hundred higher as compared to ddA 1. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00265-5

文献信息

• Process to produce 2', 3'-Dideoxynucleosides
  申请人：Bristol-Myers Squibb Company

  公开号：EP0285884A2

  公开（公告）日：1988-10-12

  There is disclosed a novel process to produce 2ʹ,3ʹ-­dideoxynucleosides such as, for example, 2ʹ,3ʹ-dideoxy­cytidine, in high yields. More particularly, the various stereoisomers of 2ʹ,3ʹ-dideoxynucleosides are obtained. The α- and β-(L)-2ʹ,3ʹ-dideoxynucleosides and certain α-(D)-2ʹ,3ʹ-dideoxynucleosides are obtained as stereo­chemically pure compounds not heretofore obtained. The compounds so produced are useful as antiviral and antibiotic agents.

  本发明公开了一种高产率生产2ʹ,3ʹ-二脱氧核苷（如2ʹ,3ʹ-二脱氧胞苷）的新工艺。更特别的是，可以获得 2ʹ，3ʹ-二脱氧核苷的各种立体异构体。α-和β-(L)-2ʹ,3ʹ-二脱氧核苷以及某些α-(D)-2ʹ,3ʹ-二脱氧核苷是以前未曾获得的立体化学纯化合物。这些化合物可用作抗病毒剂和抗生素。
• FARINA, VITTORIO;BENIGNI, DANIEL A., TETRAHEDRON LETT., 29,(1988) N 11, 1239-1242
  作者：FARINA, VITTORIO、BENIGNI, DANIEL A.

  DOI：——

  日期：——
• 2',3' DIDEOXYRIBOFURANOXIDE DERIVATIVES
  申请人：NYCOMED AS

  公开号：EP0342203A1

  公开（公告）日：1989-11-23
• US5011774A
  申请人：——

  公开号：US5011774A

  公开（公告）日：1991-04-30
• [EN] 2',3' DIDEOXYRIBOFURANOXIDE DERIVATIVES
  申请人：NYCOMED A.S.

  公开号：WO1988007532A1

  公开（公告）日：1988-10-06

  (EN) Compounds of formula (I) possess improved antiviral properties, especially in the treatment of neurological disorders caused by neurotropic viruses, for instance HIV infections. In the above formula R is an acyl group derived from a carboxylic acid or a carbonic acid, and X is a thymine or hypoxanthine group or an optionally N-acylated cytosine, adenine or guanine group; when X is an acylated group R may also be a hydrogen atom.(FR) Des composés de formule (I), possèdent des propriétés antivirales améliorées, en particulier dans le traitement de troubles neurologiques causés par des virus neurotropiques, par exemple des infections HIV. Dans la formule ci-dessus R représente un groupe acyle dérivé d'un acide carboxylique ou d'un acide carbonique, et X représente un groupe de thymine ou d'hypoxanthine, ou un groupe facultatif de cytosine, adenine ou guanine N-acylées; lorsque X représente un groupe acylé, R peut également représenter un atome d'hydrogène.