benzyl (2R,3S)-2-(iodomethyl)-5-oxotetrahydrofuran-3-ylcarbamate | 281208-46-6

• 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 (2R,3S)-2-(iodomethyl)-5-oxotetrahydrofuran-3-ylcarbamate
• 英文别名: benzyl N-[(2R,3S)-2-(iodomethyl)-5-oxooxolan-3-yl]carbamate
• CAS: 281208-46-6
• 化学式: C₁₃H₁₄INO₄
• 分子量: 375.163
• InChiKey: DDHXZJPZHHEOLJ-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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 (2R,3S)-2-(iodomethyl)-5-oxotetrahydrofuran-3-ylcarbamate 在 palladium on activated charcoal copper(l) iodide 、 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， -50.0 ℃ 、101.33 kPa 条件下， 反应 1.5h， 生成 (4S,5S)-4-amino-5-(cyclohexylmethyl)-dihydrofuran-2(3H)-one
  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 碘 、 silver trifluoromethanesulfonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.5h， 生成 benzyl (2R,3S)-2-(iodomethyl)-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