3-bromo-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine | 908143-17-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡唑并[3，4-d]嘧啶糖苷
• 英文名称: 3-bromo-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine
• 英文别名: [(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(4,6-diamino-3-bromopyrazolo[3,4-d]pyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 908143-17-9
• 化学式: C₃₁H₂₅BrN₆O₇
• 分子量: 673.48
• InChiKey: NLMXETBCFZKTIP-TXJANDSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  184
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-bromo-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine 在 吡啶 、 甲醇 、 sodium methylate 、 silver nitrate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成
  参考文献：
  名称：

  7-SUBSTITUTED 8-AZA-7-DEAZAPURINES AND 2,8-DIAZA-7-DEAZA-PURINES: SYNTHESIS OF NUCLEOSIDES AND OLIGONUCLEOTIDES

  摘要：

  7-Substituted 8-aza-7-deazaadenosines la-e were synthesized by Sonogashira cross coupling from the corresponding 7-iodo nucleoside in 36- 79% yields. Starting from 7-bromo (or 7-iodo)-8-aza- 7-deazaadenine, 2a,b were obtained by acid-catalyzed glycosylation followed by deprotection in 53 and 35% yields, respectively. Compounds 2b was applied to cross coupling reaction to give 2c-d in 34-95% yield. Compounds 2a and 4b were further transformed to the phosphoramidites 5 and 6b in 9 and 49% overall yields, which were incorporated into oligonucleotides.

  DOI：

  10.1081/ncn-200059218
• 作为产物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 、 3-溴-1H-吡唑并[3,4-d]嘧啶-4,6-二胺 在 三氟化硼乙醚 作用下， 以 硝基甲烷 为溶剂， 以70%的产率得到3-bromo-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine
  参考文献：
  名称：

  7-SUBSTITUTED 8-AZA-7-DEAZAPURINES AND 2,8-DIAZA-7-DEAZA-PURINES: SYNTHESIS OF NUCLEOSIDES AND OLIGONUCLEOTIDES

  摘要：

  7-Substituted 8-aza-7-deazaadenosines la-e were synthesized by Sonogashira cross coupling from the corresponding 7-iodo nucleoside in 36- 79% yields. Starting from 7-bromo (or 7-iodo)-8-aza- 7-deazaadenine, 2a,b were obtained by acid-catalyzed glycosylation followed by deprotection in 53 and 35% yields, respectively. Compounds 2b was applied to cross coupling reaction to give 2c-d in 34-95% yield. Compounds 2a and 4b were further transformed to the phosphoramidites 5 and 6b in 9 and 49% overall yields, which were incorporated into oligonucleotides.

  DOI：

  10.1081/ncn-200059218

文献信息

• Pyrazolo[3,4-d]pyrimidine ribonucleosides related to 2-aminoadenosine and isoguanosine: synthesis, deamination and tautomerism
  作者：Frank Seela、Kuiying Xu

  DOI：10.1039/b708736e

  日期：——

  than that of the related purines. The pK(a) values indicate that the 7-non-functionalized nucleosides 1a (pK(a) 5.8) and 15 (pK(a) 6.4) are possibly protonated in neutral conditions when incorporated into RNA. The nucleosides 3a-d exist predominantly in the keto (lactam) form with K(TAUT) (keto/enol) values of 400-1200 compared to 10(3)-10(4) for pyrrolo[2,3-d]pyrimidine isoguanosine derivatives 4a-c

  描述了与2-氨基腺苷和异鸟苷相关的8-氮杂-7-脱氮嘌呤（吡唑并[3,4-d]嘧啶）核糖核苷的合成和性质。在BF（3）存在下，将1-氮-乙酰基2,3,5-三-O-苯甲酰基-β-D-呋喃呋喃糖与8-氮杂7-脱氮嘌呤-2,6-二胺5糖基化。 ）x Et（2）O作为催化剂，得到N（8）异构体14（73％）和痕量的N（9）异构体13a（4.8％）。在相同的反应条件下，7-卤代8-氮杂-7-脱氮嘌呤-2,6-二胺6-8提供了热力学上更稳定的N（9）核苷13b-d作为唯一产物（53-70％）。因此，位置7的卤素将糖基化作用从N（8）转移到N（9）。通过2-氨基的重氮化将8-氮杂-7-脱氮嘌呤-4，6-二胺核糖核苷1a-d转化为异鸟苷衍生物3a-d。尽管化合物1a b。在7位（酶结合位点）不含氮，它们被腺苷脱氨酶脱氨；但是，它们的脱氨速度比相关嘌呤的速度要慢得多。pK（a）值表明，将7个非功能化核苷1a（pK（a）5
• 7-SUBSTITUTED 8-AZA-7-DEAZAPURINES AND 2,8-DIAZA-7-DEAZA-PURINES: SYNTHESIS OF NUCLEOSIDES AND OLIGONUCLEOTIDES
  作者：Wenqing Lin、Kuiying Xu、Frank Seela

  DOI：10.1081/ncn-200059218

  日期：2005.4.1

  7-Substituted 8-aza-7-deazaadenosines la-e were synthesized by Sonogashira cross coupling from the corresponding 7-iodo nucleoside in 36- 79% yields. Starting from 7-bromo (or 7-iodo)-8-aza- 7-deazaadenine, 2a,b were obtained by acid-catalyzed glycosylation followed by deprotection in 53 and 35% yields, respectively. Compounds 2b was applied to cross coupling reaction to give 2c-d in 34-95% yield. Compounds 2a and 4b were further transformed to the phosphoramidites 5 and 6b in 9 and 49% overall yields, which were incorporated into oligonucleotides.