7-[2'-Desoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-methoxy-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin | 98891-40-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7-[2'-Desoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-methoxy-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin
• 英文别名: [(2R,3S,5R)-5-(4-methoxy-2-methylsulfanylpyrrolo[2,3-d]pyrimidin-7-yl)-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 98891-40-8
• 化学式: C₂₉H₂₉N₃O₆S
• 分子量: 547.632
• InChiKey: IEKGSYFOAZXQAE-RBZQAINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  7-[2'-Desoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-methoxy-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以570 mg的产率得到7-(2'-Desoxy-β-D-erythro-pentofuranosyl)-4-methoxy-2-methylthio-7H-pyrrolo<2,3-d>pyrimidin
  参考文献：
  名称：

  7-Deaza-2′-deoxyinosine: A Stable Nucleoside with the Ambiguous Base Pairing Properties of 2′-Deoxyinosine

  摘要：

  The base pairing ambiguity of 7-deaza-2'-deoxyinosine (c(7)Id, 2) was studied and was found to be the same as that of 2'-deoxyinosine. The duplex stability decreases in the order [d(c(7)I-C) > d(c(7)I-A) > d(c(7)I-T) > d(c(7)I-G)]. Modified nucleosides were used to probe the various base pair motifs which were the same for dl and c(7)I(d). The 7-deazapurine nucleoside (2) is extremely stable against acid or base. As oligonucleotides can be prepared using phosphoramidite chemistry and DNA is accessible by enzymic polymerisation of the triphosphate of 2, the latter can be used as an universal nucleoside for the sequencing of DNA by chemical degradation and is otherwise a facile substitute of 2'-deoxyinosine when stability in acidic or alkaline solution is required.

  DOI：

  10.1080/15257779908043087
• 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 、 4-甲氧基-2-甲基磺酰基-7h-吡咯并(2,3-d)嘧啶 在 氢氧化钾 作用下， 生成 7-[2'-Desoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-methoxy-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin
  参考文献：
  名称：

  Regioselectivity of the Mannich Reaction on Pyrrolo[2,3-d]pyrimidine Nucleosides Related to 7-Deaza-2'-deoxyadenosine or 7-Deaza-2'-deoxyguanosine

  摘要：

  Mannich 反应在 7-deazapurine 2'-脱氧核苷上进行，并研究了区域选择性。7-deaza-2'-二氧腺苷（2'-脱氧结核菌素，4a）生成了 7-取代的 Mannich 基（5a）。当使用 7-deaza-2'-脱氧鸟苷时，侧链在 8 位引入（Mannich 基 7a）。当在 4-甲氧基-2-甲硫基-7H-吡咯[2,3-d]嘧啶 2'-脱氧核苷（12）上进行反应时，区域选择性从 8 位改变回 7 位。因此，在去甲基化和氧化甲硫基后，通过用氨取代氧化的 2-取代基，可以得到 7-取代的 7-deaza-2'-脱氧鸟苷的 Mannich 产品。

  DOI：

  10.1055/s-1997-1305

文献信息

• Regioselectivity of the Mannich Reaction on Pyrrolo[2,3-d]pyrimidine Nucleosides Related to 7-Deaza-2'-deoxyadenosine or 7-Deaza-2'-deoxyguanosine
  作者：Frank Seela

  DOI：10.1055/s-1997-1305

  日期：1997.9

  Mannich reactions were performed on 7-deazapurine 2'-deoxyribonucleosides and the regioselectivity was studied. 7-Deaza-2'-dioxyadenosine (2'-deoxytubercidin, 4a) furnished the 7-substituted Mannich base 5a. The side chain was introduced in the 8-position when 7-deaza-2'-deoxyguanosine was used (Mannich base 7a). The regioselectivity changed back from position 8 to 7 when the reaction was performed on 4-methoxy-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine 2'-deoxyribonucleoside (12). Thus a 7-substituted Mannich product of 7-deaza-2'-deoxyguanosine could be obtained after demethylation and oxidation of the methylthio group followed by displacement of the oxidized 2-substituent with ammonia.

  Mannich 反应在 7-deazapurine 2'-脱氧核苷上进行，并研究了区域选择性。7-deaza-2'-二氧腺苷（2'-脱氧结核菌素，4a）生成了 7-取代的 Mannich 基（5a）。当使用 7-deaza-2'-脱氧鸟苷时，侧链在 8 位引入（Mannich 基 7a）。当在 4-甲氧基-2-甲硫基-7H-吡咯[2,3-d]嘧啶 2'-脱氧核苷（12）上进行反应时，区域选择性从 8 位改变回 7 位。因此，在去甲基化和氧化甲硫基后，通过用氨取代氧化的 2-取代基，可以得到 7-取代的 7-deaza-2'-脱氧鸟苷的 Mannich 产品。
• Seela, Frank; Menkhoff, Sabine, Liebigs Annalen der Chemie, 1985, # 7, p. 1360 - 1366
  作者：Seela, Frank、Menkhoff, Sabine

  DOI：——

  日期：——
• 7-Deaza-2′-deoxyinosine: A Stable Nucleoside with the Ambiguous Base Pairing Properties of 2′-Deoxyinosine
  作者：Frank Seela、Cathrin Mittelbach

  DOI：10.1080/15257779908043087

  日期：1999.3

  The base pairing ambiguity of 7-deaza-2'-deoxyinosine (c(7)Id, 2) was studied and was found to be the same as that of 2'-deoxyinosine. The duplex stability decreases in the order [d(c(7)I-C) > d(c(7)I-A) > d(c(7)I-T) > d(c(7)I-G)]. Modified nucleosides were used to probe the various base pair motifs which were the same for dl and c(7)I(d). The 7-deazapurine nucleoside (2) is extremely stable against acid or base. As oligonucleotides can be prepared using phosphoramidite chemistry and DNA is accessible by enzymic polymerisation of the triphosphate of 2, the latter can be used as an universal nucleoside for the sequencing of DNA by chemical degradation and is otherwise a facile substitute of 2'-deoxyinosine when stability in acidic or alkaline solution is required.