4-amino-5-cyano-7-(3-O-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine | 119483-96-4

• 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: 4-amino-5-cyano-7-(3-O-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: 3'-O-methyltoyocamycin；4-amino-7-[(2R,3R,4S,5R)-3-hydroxy-5-(hydroxymethyl)-4-methoxyoxolan-2-yl]pyrrolo[2,3-d]pyrimidine-5-carbonitrile
• CAS: 119483-96-4
• 化学式: C₁₃H₁₅N₅O₄
• 分子量: 305.293
• InChiKey: CXXXBUYCUDDIRD-QYVSTXNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-amino-5-cyano-7-(3-O-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 在 三丁基膦 、 双氧水 作用下， 以 吡啶 、 水 为溶剂， 反应 6.0h， 生成 mycalisine A
  参考文献：
  名称：

  A total synthesis of mycalisine A

  摘要：

  In this paper, we report a total synthesis of a naturally occurring pyrrolo[2,3-d]pyrimidine nucleoside, mycalisine A. Our synthetic strategy uses D-xylose as the starting material and Vorbruggen glycosylation as the key step. Mycalisine A was synthesized in 11 steps with a 15% overall yield. (C) 2013 Qiang Xiao. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.03.014
• 作为产物：
  描述：

  4-amino-6-bromo-5-cyano-7-(2-O-acetyl-3-O-methyl-5-O-benzoyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 在 氨 、 氢气 、 palladium(II) hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.0h， 生成 4-amino-5-cyano-7-(3-O-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  A total synthesis of mycalisine A

  摘要：

  In this paper, we report a total synthesis of a naturally occurring pyrrolo[2,3-d]pyrimidine nucleoside, mycalisine A. Our synthetic strategy uses D-xylose as the starting material and Vorbruggen glycosylation as the key step. Mycalisine A was synthesized in 11 steps with a 15% overall yield. (C) 2013 Qiang Xiao. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.03.014

文献信息

• A total synthesis of the naturally occurring pyrrolo[2,3-]pyrimidine nucleoside, mycalisine A
  作者：Eric A. Meade、Steven H. Krawczyk、Leroy B. Townsend*

  DOI：10.1016/s0040-4039(00)80420-7

  日期：1988.1
• MEADE, ERIC A.;KRAWCZYK, STEVEN H.;TOWNSEND, LEROY B., TETRAHEDRON LETT., 29,(1988) N 33, C. 4073-4076
  作者：MEADE, ERIC A.、KRAWCZYK, STEVEN H.、TOWNSEND, LEROY B.

  DOI：——

  日期：——
• A total synthesis of mycalisine A
  作者：Yan-Hui Dou、Hai-Xin Ding、Ru-Chun Yang、Wei Li、Qiang Xiao

  DOI：10.1016/j.cclet.2013.03.014

  日期：2013.5

  In this paper, we report a total synthesis of a naturally occurring pyrrolo[2,3-d]pyrimidine nucleoside, mycalisine A. Our synthetic strategy uses D-xylose as the starting material and Vorbruggen glycosylation as the key step. Mycalisine A was synthesized in 11 steps with a 15% overall yield. (C) 2013 Qiang Xiao. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.