((1R)-2-hydroxy-1-hydroxymethylpent-4-enyl)carbamic acid tert-butyl ester | 220317-63-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ((1R)-2-hydroxy-1-hydroxymethylpent-4-enyl)carbamic acid tert-butyl ester
• 英文别名: tert-butyl 1,3-dihydroxyhex-5-en-2-ylcarbamate；tert-butyl N-[(2R)-1,3-dihydroxyhex-5-en-2-yl]carbamate
• CAS: 220317-63-5
• 化学式: C₁₁H₂₁NO₄
• 分子量: 231.292
• InChiKey: QSFMUAHXCQCWCC-VEDVMXKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ((1R)-2-hydroxy-1-hydroxymethylpent-4-enyl)carbamic acid tert-butyl ester 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium hydride 、 对甲苯磺酸 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (4aR,7aS)-2,2-Dimethyl-tetrahydro-[1,3]dioxino[5,4-b]pyrrole-5-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Chromium(II) chloride-mediated coupling reactions of Garner aldehyde with allyl bromides: facile asymmetric synthesis of (2R,3S )-3-hydroxy-2-hydroxymethylpyrrolidine

  摘要：

  氯化铬（II）介导的 1,1-二甲基乙基 (S)- 和 (R)-4- 甲酰基-2,2-二甲基恶唑烷-3-羧酸酯[(S)- 和 (R)-Garner 醛 ]（1a,b）与烯丙基溴 2a-c 的偶联反应以中等至良好的立体选择性进行，以良好的产率得到相应的均烯丙基醇 3a-d。均烯丙基醇 3b 很容易转化为 (2R,3S)-3-羟基-2-羟甲基吡咯烷 8。

  DOI：

  10.1039/a805998e
• 作为产物：
  描述：

  tert-butyl N-[(1R)-1-(hydroxymethyl)-2-[methoxy(methyl)amino]-2-oxo-ethyl]carbamate 在 咪唑 、 sodium tetrahydroborate 、 四丁基氟化铵 、 叔丁基二甲基氯硅烷 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.17h， 生成 ((1R)-2-hydroxy-1-hydroxymethylpent-4-enyl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  SAR and Structural Analysis of Siderophore-Conjugated Monocarbam Inhibitors of Pseudomonas aeruginosa PBP3

  摘要：

  A main challenge in the development of new agents for the treatment of Pseudomonas aeruginosa infections is the identification of chemotypes that efficiently penetrate the cell envelope and are not susceptible to established resistance mechanisms. Siderophore-conjugated monocarbams are attractive because of their ability to hijack the bacteria's iron uptake machinery for transport into the periplasm and their inherent stability to metallo-beta-lactamases. Through development of the SAR we identified a number of modifications to the scaffold that afforded active anti-P. aeruginosa agents with good physicochemical properties. Through crystallographic efforts we gained a better understanding into how these compounds bind to the target penicillin binding protein PBP3 and factors to consider for future design.

  DOI：

  10.1021/acsmedchemlett.5b00026

文献信息

• Pseudodistomin C, a new piperidine alkaloid with unusual absolute configuration from the Okinawan tunicate Pseudodistoma kanoko
  作者：Jun'ichi Kobayashi、Kazushi Naitoh、Yukiko Doi、Kanako Deki、Masami Ishibashi

  DOI：10.1021/jo00126a053

  日期：1995.10

  Pseudodistomin C, a new cytotoxic piperidine alkaloid, was isolated from the Okinawan tunicate Pseudodistoma kanoko and the structure elucidated by spectral data, chemical degradations, and synthesis. The absolute configurations of the C-4 and C-5 chiral centers of pseudodistomin C were revealed by chiral HPLC analysis to be 4S and 5R, which were opposite to those of pseudodistomins A and B, previously isolated from the same tunicate, having the same planar structure as to the piperidine nucleus.
• Chromium(II) chloride-mediated coupling reactions of Garner aldehyde with allyl bromides: facile asymmetric synthesis of (2R,3S )-3-hydroxy-2-hydroxymethylpyrrolidine
  作者：Yutaka Aoyagi、Haruko Inaba、Yukiko Hiraiwa、Asako Kuroda、Akihiro Ohta

  DOI：10.1039/a805998e

  日期：——

  Chromium(II) chloride-mediated coupling reactions of 1,1-dimethylethyl (S)- and (R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylates [(S)- and (R)-Garner aldehydes ] (1a,b) with allyl bromides 2a–c proceeded with moderate to good stereoselectivity to give the corresponding homoallyl alcohols 3a–d in good yields. The homoallyl alcohol 3b was easily transformed to (2R,3S)-3-hydroxy-2-hydroxymethylpyrrolidine 8.

  氯化铬（II）介导的 1,1-二甲基乙基 (S)- 和 (R)-4- 甲酰基-2,2-二甲基恶唑烷-3-羧酸酯[(S)- 和 (R)-Garner 醛 ]（1a,b）与烯丙基溴 2a-c 的偶联反应以中等至良好的立体选择性进行，以良好的产率得到相应的均烯丙基醇 3a-d。均烯丙基醇 3b 很容易转化为 (2R,3S)-3-羟基-2-羟甲基吡咯烷 8。
• SAR and Structural Analysis of Siderophore-Conjugated Monocarbam Inhibitors of <i>Pseudomonas aeruginosa</i> PBP3
  作者：Kerry E. Murphy-Benenato、Brian Dangel、Hajnalka E. Davis、Thomas F. Durand-Réville、Andrew D. Ferguson、Ning Gao、Haris Jahić、John P. Mueller、Erika L. Manyak、Olga Quiroga、Michael Rooney、Li Sha、Mark Sylvester、Frank Wu、Mark Zambrowski、Shannon X. Zhao

  DOI：10.1021/acsmedchemlett.5b00026

  日期：2015.5.14

  A main challenge in the development of new agents for the treatment of Pseudomonas aeruginosa infections is the identification of chemotypes that efficiently penetrate the cell envelope and are not susceptible to established resistance mechanisms. Siderophore-conjugated monocarbams are attractive because of their ability to hijack the bacteria's iron uptake machinery for transport into the periplasm and their inherent stability to metallo-beta-lactamases. Through development of the SAR we identified a number of modifications to the scaffold that afforded active anti-P. aeruginosa agents with good physicochemical properties. Through crystallographic efforts we gained a better understanding into how these compounds bind to the target penicillin binding protein PBP3 and factors to consider for future design.