(1S)-N-(tert-butoxycarbonyl)-1-(p-carbomethoxyamino-phenyl)-1,4-dideoxy-1,4-imino-D-ribitol | 501096-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (1S)-N-(tert-butoxycarbonyl)-1-(p-carbomethoxyamino-phenyl)-1,4-dideoxy-1,4-imino-D-ribitol
• 英文别名: tert-butyl (2R,3R,4S,5S)-3,4-dihydroxy-2-(hydroxymethyl)-5-[4-(methoxycarbonylamino)phenyl]pyrrolidine-1-carboxylate
• CAS: 501096-30-6
• 化学式: C₁₈H₂₆N₂O₇
• 分子量: 382.414
• InChiKey: XBMBIUNCUODCBY-BARDWOONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1S)-N-(tert-butoxycarbonyl)-1-(p-carbomethoxyamino-phenyl)-1,4-dideoxy-1,4-imino-D-ribitol 在 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以100%的产率得到[4-((2S,3S,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl-pyrrolidin-2-yl)-phenyl]-carbamic acid methyl ester
  参考文献：
  名称：

  Probing the Stereoselectivity of the Heck Arylation of Endocyclic Enecarbamates with Diazonium Salts. Concise Syntheses of (2S,5R)-Phenylproline Methyl Ester and Schramm's C-Azanucleoside

  摘要：

  [GRAPHICS]The diastereoselectivity of the Heck arylation of several chiral, nonracemic, five-membered endocyclic enecarbamates with aryldiazonium tetrafluoroborates was evaluated. The cis selectivity observed for some enecarbamates bearing coordinating groups was explored in the concise synthesis of the (2S,5R)-(+)-phenylproline methyl ester, a scaffold for the nonpeptide cholecystokinin antagonist (+)-RP 66803, and in the synthesis of Schramm's potent antiprotozoan C-azanucleoside.

  DOI：

  10.1021/ol027268a
• 作为产物：
  描述：

  (S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-2,3-dihydro-pyrrole-1-carboxylic acid tert-butyl ester 在 potassium osmate(VI) 、 tris-(dibenzylideneacetone)dipalladium(0) 、 四丁基氟化铵 、 sodium acetate 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 丙酮 、 乙腈 、 叔丁醇 为溶剂， 反应 4.5h， 生成 (1S)-N-(tert-butoxycarbonyl)-1-(p-carbomethoxyamino-phenyl)-1,4-dideoxy-1,4-imino-D-ribitol
  参考文献：
  名称：

  Probing the Stereoselectivity of the Heck Arylation of Endocyclic Enecarbamates with Diazonium Salts. Concise Syntheses of (2S,5R)-Phenylproline Methyl Ester and Schramm's C-Azanucleoside

  摘要：

  [GRAPHICS]The diastereoselectivity of the Heck arylation of several chiral, nonracemic, five-membered endocyclic enecarbamates with aryldiazonium tetrafluoroborates was evaluated. The cis selectivity observed for some enecarbamates bearing coordinating groups was explored in the concise synthesis of the (2S,5R)-(+)-phenylproline methyl ester, a scaffold for the nonpeptide cholecystokinin antagonist (+)-RP 66803, and in the synthesis of Schramm's potent antiprotozoan C-azanucleoside.

  DOI：

  10.1021/ol027268a

文献信息

• Probing the Stereoselectivity of the Heck Arylation of Endocyclic Enecarbamates with Diazonium Salts. Concise Syntheses of (2<i>S</i>,5<i>R</i>)-Phenylproline Methyl Ester and Schramm's C-Azanucleoside
  作者：Elias A. Severino、Edson R. Costenaro、Ariel L. L. Garcia、Carlos Roque D. Correia

  DOI：10.1021/ol027268a

  日期：2003.2.1

  [GRAPHICS]The diastereoselectivity of the Heck arylation of several chiral, nonracemic, five-membered endocyclic enecarbamates with aryldiazonium tetrafluoroborates was evaluated. The cis selectivity observed for some enecarbamates bearing coordinating groups was explored in the concise synthesis of the (2S,5R)-(+)-phenylproline methyl ester, a scaffold for the nonpeptide cholecystokinin antagonist (+)-RP 66803, and in the synthesis of Schramm's potent antiprotozoan C-azanucleoside.