[4-((2S,3S,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl-pyrrolidin-2-yl)-phenyl]-carbamic acid methyl ester | 501096-31-7

• 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: [4-((2S,3S,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl-pyrrolidin-2-yl)-phenyl]-carbamic acid methyl ester
• 英文别名: methyl N-[4-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]phenyl]carbamate
• CAS: 501096-31-7
• 化学式: C₁₃H₁₈N₂O₅
• 分子量: 282.296
• InChiKey: ZNGYHRBYZFVZJN-KXNHARMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  111
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [4-((2S,3S,4R,5R)-3,4-Dihydroxy-5-hydroxymethyl-pyrrolidin-2-yl)-phenyl]-carbamic acid methyl ester 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 30.0h， 生成 (2S,3S,4R,5R)-2-(4-aminophenyl)-5-(hydroxymethyl)pyrrolidine-3,4-diol
  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 、 乙酰氯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 、 乙腈 、 叔丁醇 为溶剂， 反应 5.0h， 生成 [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

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.