5-[[[[(phenylmethoxy)carbonyl]amino]carbonyl]amino]-1-(β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid diphenylmethyl ester | 151416-18-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: 5-[[[[(phenylmethoxy)carbonyl]amino]carbonyl]amino]-1-(β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid diphenylmethyl ester
• 英文别名: 5-[[[[(phenylmethoxy)carbonyl]amino]carbonyl]amino]-1-(beta-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid diphenylmethyl ester；benzhydryl 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(phenylmethoxycarbonylcarbamoylamino)imidazole-4-carboxylate
• CAS: 151416-18-1
• 化学式: C₃₁H₃₀N₄O₉
• 分子量: 602.601
• InChiKey: SHCHWRLXGQVAHT-ZYWWQZICSA-N

物化性质

• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  44
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  182
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-[[[[(phenylmethoxy)carbonyl]amino]carbonyl]amino]-1-(β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid diphenylmethyl ester 在 palladium on activated charcoal 1-(3-dimethylaminopropyl)-3-ethylcarbodiinide hydrochloride 、 氢气 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 5-氨基-3-beta-D-呋喃核糖基咪唑并(4,5-d)(1,3)恶嗪-7(3H)-酮
  参考文献：
  名称：

  A novel synthesis of oxanosine and 1-thiaguanosine

  摘要：

  A novel total synthesis of oxanosine has been developed. The key heterocycle forming reaction of this synthesis is the carbodiimide mediated dehydration and cyclization of an urea-acid derived from AICA-riboside. The same procedure was also applied to the synthesis of 1-thiaguanosine.

  DOI：

  10.1016/s0040-4039(00)79951-5
• 作为产物：
  描述：

  benzyloxycarbonyl isocyanate 在 氢氧化钾 、 1,2-二氯乙烷 作用下， 以 甲醇 为溶剂， 生成 5-[[[[(phenylmethoxy)carbonyl]amino]carbonyl]amino]-1-(β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid diphenylmethyl ester
  参考文献：
  名称：

  A novel synthesis of oxanosine and 1-thiaguanosine

  摘要：

  A novel total synthesis of oxanosine has been developed. The key heterocycle forming reaction of this synthesis is the carbodiimide mediated dehydration and cyclization of an urea-acid derived from AICA-riboside. The same procedure was also applied to the synthesis of 1-thiaguanosine.

  DOI：

  10.1016/s0040-4039(00)79951-5

文献信息

• 1-thiaguanosine and process for preparing oxanosine and 1-thiaguanosine
  申请人：Hoffmann-La Roche Inc.

  公开号：US05243042A1

  公开（公告）日：1993-09-07

  The invention relates to antibacterially active 5-amino-3-(.beta.-D-ribofuranosyl)imidazo[4,5-d][1,3]thiazin-7(3H)-one, also referred to as 1-thiaguanosine, a composition and method comprising the same and processes and intermediates for the preparation of 1-thiaguanosine and 5-amino-3-(.beta.-D-ribofuranosyl)imidazo[4,5-d][1,3]oxazin-7(3H)-one, also referred to as oxanosine, a known compound.

  本发明涉及一种具有抗菌活性的5-氨基-3-(β-D-核糖呋喃基)咪唑[4,5-d][1,3]噻嗪-7(3H)-酮，也称为1-硫鸟苷，以及包含该化合物的组合物和方法，以及制备1-硫鸟苷和5-氨基-3-(β-D-核糖呋喃基)咪唑[4,5-d][1,3]噁唑-7(3H)-酮，也称为噁鸟苷，的过程和中间体。
• US5243042A
  申请人：——

  公开号：US5243042A

  公开（公告）日：1993-09-07
• A novel synthesis of oxanosine and 1-thiaguanosine
  作者：Kin-Chun Luk、Douglas W. Moore、Dennis D. Keith

  DOI：10.1016/s0040-4039(00)79951-5

  日期：1994.2

  A novel total synthesis of oxanosine has been developed. The key heterocycle forming reaction of this synthesis is the carbodiimide mediated dehydration and cyclization of an urea-acid derived from AICA-riboside. The same procedure was also applied to the synthesis of 1-thiaguanosine.