5-chloro-1,7-dihydro-4-methoxy-7-(β-D-ribofuranosyl)-2H-pyrrolo[2,3-d]pyrimidin-2-one | 873792-77-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 英文名称: 5-chloro-1,7-dihydro-4-methoxy-7-(β-D-ribofuranosyl)-2H-pyrrolo[2,3-d]pyrimidin-2-one
• 英文别名: 5-chloro-7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidin-2-one
• CAS: 873792-77-9
• 化学式: C₁₂H₁₄ClN₃O₆
• 分子量: 331.713
• InChiKey: OHZNWSVXXRMHRB-IOSLPCCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-chloro-1,7-dihydro-4-methoxy-7-(β-D-ribofuranosyl)-2H-pyrrolo[2,3-d]pyrimidin-2-one 在 sodium hydroxide 作用下， 以75%的产率得到5-chloro-7-(β-D-ribofuranosyl)-1,2,3,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  有效合成的7功能7-脱氮嘌呤β-D-或β-L-核糖核苷：吡咯并[2,3-D]嘧啶与1-O-乙酰基-2,3,5-Tri-O-苄基的糖基化-D-或L-呋喃核糖

  摘要：

  描述了使用可商购的1-O-乙酰基-2,3,5-三-O-苯甲酰基-D-或L-呋喃呋喃糖酶用7-卤代7-脱氮嘌呤进行的糖基化反应。

  DOI：

  10.1080/15257770701490332
• 作为产物：
  描述：

  在 三氟甲磺酸三甲基硅酯 、 溶剂黄146 、 sodium nitrite 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 27.0h， 生成 5-chloro-1,7-dihydro-4-methoxy-7-(β-D-ribofuranosyl)-2H-pyrrolo[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  7-Functionalized 7-Deazapurine Ribonucleosides Related to 2-Aminoadenosine, Guanosine, and Xanthosine:  Glycosylation of Pyrrolo[2,3-d]pyrimidines with 1-O-Acetyl-2,3,5-tri-O-benzoyl-d-ribofuranose

  摘要：

  The Silyl-Hilbert-Johnson reaction as well as the nucleobase-anion glycosylation of a series of 7-deazapurines has been investigated, and the 7-functionalized 7-deazapurine ribonucleosides were prepared. Glycosylation of the 7-halogenated 6-chloro-2-pivaloylamino-7-deazapurines 9b-d with 1-O-acetyl2,3,5-tri-O-benzOyl-D-ribofuranose (5) gave the beta-D-nucleosides 11b-d (73-75% yield), which were transformed to a number of novel 7-halogenated 7-deazapurine ribonucleosides (2b-d, 3b-d, and 4b-d) related to guanosine, 2-aminoadenosine, and xanthosine. 7-Alkynyl derivatives (2e-i, 3e-h, or 4g) have been prepared from the corresponding 7-iodonucleosides 2d, 3d, or 4d employing the palladium-catalyzed Sonogashira cross-coupling reaction. The 7-halogenated 2-amino-7-deazapurine ribonucleosides with a reactive 6-chloro substituent (18b-d) were synthesized in an alternative way using nucleobase-anion glycosylation performed on the 7-halogenated 2-arnino-6-chloro-7-deazapurines 13b-d with 5-0-[(1,1dimethylethyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-alpha-D-ribofuranosyl chloride (17). Compounds 18b-d have been converted to the nucleosides 19b-d carrying reactive substituents in the pyrimidine moiety. Conformational analysis of selected nucleosides on the basis of proton coupling constants and using the program PSEUROT showed that these ribonucleosides exist in a preferred S conformation in solution.

  DOI：

  10.1021/jo0516640

文献信息

• An Efficient Synthesis Of 7-Functionalized 7-Deazapurine β-D- Or β-L-Ribonucleosides: Glycosylation Of Pyrrolo[2,3-D]Pyrimidines With 1-O-Acetyl-2,3,5-Tri-O-Benzoyl-D-Or L-Ribofuranose
  作者：Xiaohua Peng、Frank Seela

  DOI：10.1080/15257770701490332

  日期：2007.11.26

  The glycosylation reaction performed with 7-halogenated 7-deazapurines employing commercially available 1-O-acetyl-2,3,5-tri-O-benzoyl-D- or L-ribofuranoses is described.

  描述了使用可商购的1-O-乙酰基-2,3,5-三-O-苯甲酰基-D-或L-呋喃呋喃糖酶用7-卤代7-脱氮嘌呤进行的糖基化反应。
• 7-Functionalized 7-Deazapurine Ribonucleosides Related to 2-Aminoadenosine, Guanosine, and Xanthosine:  Glycosylation of Pyrrolo[2,3-<i>d</i>]pyrimidines with 1-<i>O</i>-Acetyl-2,3,5-tri-<i>O</i>-benzoyl-<scp>d</scp>-ribofuranose
  作者：Frank Seela、Xiaohua Peng

  DOI：10.1021/jo0516640

  日期：2006.1.1

  The Silyl-Hilbert-Johnson reaction as well as the nucleobase-anion glycosylation of a series of 7-deazapurines has been investigated, and the 7-functionalized 7-deazapurine ribonucleosides were prepared. Glycosylation of the 7-halogenated 6-chloro-2-pivaloylamino-7-deazapurines 9b-d with 1-O-acetyl2,3,5-tri-O-benzOyl-D-ribofuranose (5) gave the beta-D-nucleosides 11b-d (73-75% yield), which were transformed to a number of novel 7-halogenated 7-deazapurine ribonucleosides (2b-d, 3b-d, and 4b-d) related to guanosine, 2-aminoadenosine, and xanthosine. 7-Alkynyl derivatives (2e-i, 3e-h, or 4g) have been prepared from the corresponding 7-iodonucleosides 2d, 3d, or 4d employing the palladium-catalyzed Sonogashira cross-coupling reaction. The 7-halogenated 2-amino-7-deazapurine ribonucleosides with a reactive 6-chloro substituent (18b-d) were synthesized in an alternative way using nucleobase-anion glycosylation performed on the 7-halogenated 2-arnino-6-chloro-7-deazapurines 13b-d with 5-0-[(1,1dimethylethyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-alpha-D-ribofuranosyl chloride (17). Compounds 18b-d have been converted to the nucleosides 19b-d carrying reactive substituents in the pyrimidine moiety. Conformational analysis of selected nucleosides on the basis of proton coupling constants and using the program PSEUROT showed that these ribonucleosides exist in a preferred S conformation in solution.