benzyl (2S,3S)-2-cyclohexylmethyl-5-oxotetrahydrofuran-3-ylcarbamate | 281208-50-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (2S,3S)-2-cyclohexylmethyl-5-oxotetrahydrofuran-3-ylcarbamate
• 英文别名: benzyl N-[(2S,3S)-2-(cyclohexylmethyl)-5-oxooxolan-3-yl]carbamate
• CAS: 281208-50-2
• 化学式: C₁₉H₂₅NO₄
• 分子量: 331.412
• InChiKey: HFRXXFMYLAKAPQ-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl (2S,3S)-2-cyclohexylmethyl-5-oxotetrahydrofuran-3-ylcarbamate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以96%的产率得到(4S)-4-[(1S)-2-cyclohexyl-1-hydroxyethyl]-1,3-oxazinane-2,6-dione
  参考文献：
  名称：

  Iodolactonization of 3-amino-4-pentenoic acid: a stereoselective synthesis of syn-γ-hydroxy-β-amino acids

  摘要：

  The reaction of (S)-3-N-Cbz-4-pentenoic acid with iodine in acetonitrile in the presence of AgOTf gave the cis-iodo-lactone 6 in excellent yield and in a highly diastereoselective manner. The substitutions of the iodine in 6 by different Grignard reagents in the presence of CuI and the subsequent conversions into the functionalized syn-gamma-hydroxy-beta-amino acids have been investigated. By the above reaction sequence, (3S,4S)-3-amino1-4-hydroxy-5-cyclohexyl pentanoic acid was synthesized with high enantioselectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00033-1
• 作为产物：
  描述：

  tert-butyl-(3S)-3-{[(benzyloxy)carbonyl]amino}-4-pentenoate 在 copper(l) iodide 、 碘 、 silver trifluoromethanesulfonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 7.0h， 生成 benzyl (2S,3S)-2-cyclohexylmethyl-5-oxotetrahydrofuran-3-ylcarbamate
  参考文献：
  名称：

  Iodolactonization of 3-amino-4-pentenoic acid: a stereoselective synthesis of syn-γ-hydroxy-β-amino acids

  摘要：

  The reaction of (S)-3-N-Cbz-4-pentenoic acid with iodine in acetonitrile in the presence of AgOTf gave the cis-iodo-lactone 6 in excellent yield and in a highly diastereoselective manner. The substitutions of the iodine in 6 by different Grignard reagents in the presence of CuI and the subsequent conversions into the functionalized syn-gamma-hydroxy-beta-amino acids have been investigated. By the above reaction sequence, (3S,4S)-3-amino1-4-hydroxy-5-cyclohexyl pentanoic acid was synthesized with high enantioselectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00033-1

文献信息

• Iodolactonization of 3-amino-4-pentenoic acid: a stereoselective synthesis of syn-γ-hydroxy-β-amino acids
  作者：Giuliano Delle Monache、Domenico Misiti、Patrizia Salvatore、Giovanni Zappia

  DOI：10.1016/s0957-4166(00)00033-1

  日期：2000.3

  The reaction of (S)-3-N-Cbz-4-pentenoic acid with iodine in acetonitrile in the presence of AgOTf gave the cis-iodo-lactone 6 in excellent yield and in a highly diastereoselective manner. The substitutions of the iodine in 6 by different Grignard reagents in the presence of CuI and the subsequent conversions into the functionalized syn-gamma-hydroxy-beta-amino acids have been investigated. By the above reaction sequence, (3S,4S)-3-amino1-4-hydroxy-5-cyclohexyl pentanoic acid was synthesized with high enantioselectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.