(+)-aristeromycin | 99395-42-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: (+)-aristeromycin
• 英文别名: (1S,2R,3S,5S)-3-(6-aminopurin-9-yl)-5-(hydroxymethyl)cyclopentane-1,2-diol
• CAS: 99395-42-3
• 化学式: C₁₁H₁₅N₅O₃
• 分子量: 265.272
• InChiKey: UGRNVLGKAGREKS-UXXCCHNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (+/-)-2,2-dimethyl-3αβ,6αβ-dihydro-4H-cyclopenta-1,3-dioxol-4-one 在 吡啶 、 18-冠醚-6 、 甲基叔丁基醚 、 水 、 sodium hydride 、 二异丁基氢化铝 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 (+)-aristeromycin
  参考文献：
  名称：

  Asymmetric synthesis of L-cyclopentyl carbocyclic nucleosides

  摘要：

  Asymmetric synthesis of L-carbocyclic nucleosides, (+)-beta-L-aristeromycin (11) and its thymine analog (12) was accomplished. The key intermediate 3 was synthesized by a regioselective conjugate addition to the enone 1 followed by DIBAL-H reduction. Coupling of 4 with heterocycle or construction of heterocyle by a linear approach gave 11 and 12. This is the first asymmetric synthesis of L-cyclopentyl carbocyclic nucleosides. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00898-8

文献信息

• Biocatalytical transformations—VI. The 4-acetamido-cyclopent-2-ene carboxylate route revisited: Synthesis of (+)- and (−)-aristeromycin
  作者：René Csuk、Petra Dörr

  DOI：10.1016/0040-4020(95)00246-5

  日期：1995.5

  Enantiomerically pure (+)- as well as (−)-aristeromycin can be synthesized starting from (+)- or (−)-butyl (or hexyl) 4-acetamido-cyclopent-2-ene carboxylate; these carboxylates are easily obtained from their corresponding racemates by hydrolysis with the lipase from Candida rugosa.

  对映体纯的（+）-以及（-）-阿霉素可以从4-乙酰氨基-环戊-2-烯的（+）-或（-）-丁基（或己基）羧酸酯开始合成；这些羧酸盐很容易通过用来自假丝酵母的脂肪酶水解从它们相应的外消旋物中获得。
• A Novel, One-Pot Ring Expansion of Cyclobutanones. Syntheses of Carbovir and Aristeromycin
  作者：Brian Brown、Louis S. Hegedus

  DOI：10.1021/jo9919759

  日期：2000.3.1

  A novel, one-pot ring-expansion procedure was developed using Me3S(O)I, NaH, and Sc(OTf)3. The scope and limitations were briefly examined, and a tentative mechanism was proposed. Application of the methodology to known cyclobutanone 1 provided the corresponding cyclopentanone, which was successfully advanced to (+)-carbovir and (+)-aristeromycin.

  使用Me3S（O）I，NaH和Sc（OTf）3开发了一种新颖的一锅扩环程序。简要审查了范围和局限性，并提出了一种尝试性机制。将该方法应用于已知的环丁酮1可提供相应的环戊酮，该环戊酮已成功应用于（+）-carbovir和（+）-aristeromycin。
• Resolution of racemic carbocyclic analogs of purine nucleosides through the action of adenosine deaminase. Antiviral activity of the carbocyclic 2'-deoxyguanosine enantiomers
  作者：John A. Secrist、John A. Montgomery、Y. Fulmer Shealy、C. Allen O'Dell、Sarah Jo Clayton

  DOI：10.1021/jm00387a032

  日期：1987.4

  The action of adenosine deaminase on racemic carbocyclic analogues of 6-aminopurine nucleosides was investigated. When either racemic carbocyclic adenosine [(+/-)-C-Ado] or the racemic carbocyclic analogue [(+/-)-C-2,6-DAP-2'-dR] of 2,6-diaminopurine 2'-deoxyribofuranoside was incubated with this enzyme, approximately half of the material was deaminated rapidly. From the resulting solution, the D isomers

  研究了腺苷脱氨酶对6-氨基嘌呤核苷的外消旋碳环类似物的作用。当外消旋碳环腺苷[（+/-）-C-Ado]或外消旋碳环类似物[（+/-）-C-2,6-DAP-2'-dR]为2,6-二氨基嘌呤2'-用该酶孵育脱氧核糖呋喃糖苷，将大约一半的物质快速脱氨基。从所得溶液中，分离出脱氨基碳环类似物的D异构体（D-碳环肌苷，DC-Ino或D-碳环2'-脱氧鸟苷，D-2'-CDG）和未脱碳碳环类似物的L异构体。 。在较高的酶浓度下，LC-Ado和LC-2,6-DAP-2'-dR的脱氨基反应缓慢进行，因此也使其他对映异构体可及。在针对1型和2型单纯疱疹病毒的体外测试中，D-2' -CDG与（+/-）-2'-CDG一样有效，而L-2'-CDG仅显示适度的活性。与先前报道的针对这两种病毒的（+/-）-C-2,6-DAP-2'-dR高活性和效力相反，LC-2,6-DAP-2'-dR没有活性。
• Asymmetric synthesis of L-cyclopentyl carbocyclic nucleosides
  作者：Peiyuan Wang、Luigi A. Agrofoglio、M. Gary Newton、Chung K. Chu

  DOI：10.1016/s0040-4039(97)00898-8

  日期：1997.6

  Asymmetric synthesis of L-carbocyclic nucleosides, (+)-beta-L-aristeromycin (11) and its thymine analog (12) was accomplished. The key intermediate 3 was synthesized by a regioselective conjugate addition to the enone 1 followed by DIBAL-H reduction. Coupling of 4 with heterocycle or construction of heterocyle by a linear approach gave 11 and 12. This is the first asymmetric synthesis of L-cyclopentyl carbocyclic nucleosides. (C) 1997 Elsevier Science Ltd.
• Roberts, Stanley M.; Shoberu, Karoline A., Journal of the Chemical Society. Perkin transactions I, 1991, # 4, p. 2605 - 2607
  作者：Roberts, Stanley M.、Shoberu, Karoline A.

  DOI：——

  日期：——