((2S,3R)-2-Isopropyl-4-oxo-oxetan-3-yl)-carbamic acid benzyl ester | 891833-95-7

• 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: ((2S,3R)-2-Isopropyl-4-oxo-oxetan-3-yl)-carbamic acid benzyl ester
• 英文别名: benzyl N-[(3R,4S)-2-oxo-4-propan-2-yloxetan-3-yl]carbamate
• CAS: 891833-95-7
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: UDOVVRTXVGEDAO-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  ((2S,3R)-2-Isopropyl-4-oxo-oxetan-3-yl)-carbamic acid benzyl ester 在 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 90.0h， 以46%的产率得到(2S,3R)-2-Benzyloxycarbonylamino-3-chloro-4-methyl-pentanoic acid
  参考文献：
  名称：

  Synthesis of β-chloro α-amino acids: (2S,3R)- and (2S,3S)-3-chloroleucine

  摘要：

  The first syntheses of (2S,3R)- and (2S,3S)-3-chloroleucine (3-chloro-D-leucines 1 and 2) have been achieved from D-3-hydroxyleucine and allo-D-3-hydroxyleucine, respectively, through the formation of the corresponding N-Cbz beta-lactones, followed by a ring opening promoted by lithium chloride and a debenzylation process. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.127
• 作为产物：
  描述：

  2,5-二氧代吡咯烷-1-羧酸苄酯 在 碳酸氢钠 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 ((2S,3R)-2-Isopropyl-4-oxo-oxetan-3-yl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis of β-chloro α-amino acids: (2S,3R)- and (2S,3S)-3-chloroleucine

  摘要：

  The first syntheses of (2S,3R)- and (2S,3S)-3-chloroleucine (3-chloro-D-leucines 1 and 2) have been achieved from D-3-hydroxyleucine and allo-D-3-hydroxyleucine, respectively, through the formation of the corresponding N-Cbz beta-lactones, followed by a ring opening promoted by lithium chloride and a debenzylation process. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.127

文献信息

• Synthesis of β-chloro α-amino acids: (2S,3R)- and (2S,3S)-3-chloroleucine
  作者：Nativitat Valls、Mar Borregán、Josep Bonjoch

  DOI：10.1016/j.tetlet.2006.03.127

  日期：2006.5

  The first syntheses of (2S,3R)- and (2S,3S)-3-chloroleucine (3-chloro-D-leucines 1 and 2) have been achieved from D-3-hydroxyleucine and allo-D-3-hydroxyleucine, respectively, through the formation of the corresponding N-Cbz beta-lactones, followed by a ring opening promoted by lithium chloride and a debenzylation process. (c) 2006 Elsevier Ltd. All rights reserved.