6-amino-1-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazo<4,5-c>pyridin-4(5H)-one | 147212-82-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 6-amino-1-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazo<4,5-c>pyridin-4(5H)-one
• 英文别名: 6-amino-1-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazo[4,5-c]pyridin-4(5H)-one；6-amino-1-[(2R,3R,4R,5R)-3,4-bis[[tert-butyl(dimethyl)silyl]oxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-5H-imidazo[4,5-c]pyridin-4-one
• CAS: 147212-82-6
• 化学式: C₂₉H₅₆N₄O₅Si₃
• 分子量: 625.044
• InChiKey: GSEVIPRRQRSYIQ-UCRVAIAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.01
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-amino-1-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazo<4,5-c>pyridin-4(5H)-one 在 吡啶 、 N-氯代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 6-acetamido-7-chloro-1-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazo[4,5-c]pyridin-4(5H)-one
  参考文献：
  名称：

  Nucleosides and Nucleotides. 184. Synthesis and Conformational Investigation of Anti-Fixed 3-Deaza-3-halopurine Ribonucleosides^1,2

  摘要：

  A versatile synthetic route to 3-deaza-3-haloinosines 6-8 and 46, -adenosines 15-17 and 64, and -guanosines 25, 26, and 52 is described. 3-Deaza-3-chloro-, -bromo-, and -iodopurine ribonucleosides can be synthesized by treating the 3-deazapurine ribonucleosides with N-halosuccinimides. For the synthesis of 3-deaza-3-fluoropurine ribonucleosides, 5-formylimidazole-4-carboxamide ribosides 34 and 35 prepared from 5-iodoimidazole-4-carboxamide derivatives 29 and 31 were us ed as the key intermediates. The reaction of 34 and 35 with lithium (trimethylsilyl)acetylide and sodium cyanide, respectively, followed by appropriate manipulations gave 3-deaza-3-fluoroinosine derivative 46 and 3-deaza-3-fluoroguanosine derivative 52. 3-Deaza-3-fluoroadenosine (64) was also synthesized by selective reductive deamination of 4,6-diamino-7-fluoroimidazo[4,5-c]pyridine derivative 51, followed by deprotection. A conformational analysis using H-1 NMR and NOE experiments showed that the introduction of halogens (chloro, bromo, and iodo) into the 3-position of 3-deazapurine ribonucleosides forced fixation of the glycosyl torsion angle in the anti region, but did not-abnormally influence sugar puckering. On the other hand, 3-deaza-3-fluoropurine ribonucleosides should rotate freely around the glycosyl bond.

  DOI：

  10.1021/jo990638x
• 作为产物：
  描述：

  5-ethynyl-1-β-D-ribofuranosylimidazole-4-carboxamide 在 吡啶 、 咪唑 、 盐酸羟胺 、 sodium carbonate 、 异氰酸苯酯 、 溶剂黄146 、 二甲胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 63.5h， 生成 6-amino-1-(2,3,5-tri-O-tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazo<4,5-c>pyridin-4(5H)-one
  参考文献：
  名称：

  核苷和核苷酸。116.通过5-乙炔基-1-β-D-呋喃呋喃基咪唑-4-羧酰胺或-腈的闭环，方便地合成3-脱氮杂腺苷，3-脱氮鸟苷和3-脱氮肌苷

  摘要：

  3-deazapurine核苷，3-deazainosine [1-β-D-呋喃呋喃基嘧啶并[4,5- c ] pyridin-4（5 H）-one（8）]，3-deazaguanosine [6-amino- 1-β-D-呋喃呋喃基咪唑并[4,5- c ]吡啶-4（5 H）-one（23）]和3-脱氮杂腺苷[4-氨基-1-β-D-呋喃呋喃基咪唑并[4,5- c]描述了[吡啶（29）]。该方法包括在咪唑环的4-位和5-位的取代基之间的闭环。5-乙炔基-1-β-D-呋喃呋喃基氨基咪唑-4-羧酰胺的处理（2），可以很容易地从AICA核糖苷中获得（1）），先后用二甲胺水溶液和乙酸水溶液，以64％的收率得到8。5-（2-羟基亚氨基乙基）-1-（2,3,5-三- ø -叔丁基二-β-d-D-呋喃核糖基）咪唑-4-甲酰胺（19）从合成3由治疗的二甲胺水溶液，接着由盐酸羟胺制成。通过苯基异氰酸酯实现19

  DOI：

  10.1016/s0040-4020(01)86259-1

文献信息

• Nucleosides and nucleotides. 114. A convenient method for the synthesis of 3-deazapurine nucleosides from AICA-Riboside
  作者：Noriaki Minakawa、Akira Matsuda

  DOI：10.1016/s0040-4039(00)61646-5

  日期：1993.1

  3-Deazapurine nucleosides, 3-deazainosine (6), 3-deazaguanosine (12), and 3-deazaadenosine (17), were synthesized from 5-ethynyl-1-beta-D-ribofuranosylimidazole-4-carboxamide (2) or -4-carbonitrile (13), which were readily obtained from AICA-riboside, via intramolecular ring closure.