tert-butyl [(2S,3S)-3-benzyloxy-12-hydroxy-6-oxododecan-2-yl]carbamate | 1175565-51-1

• 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: tert-butyl [(2S,3S)-3-benzyloxy-12-hydroxy-6-oxododecan-2-yl]carbamate
• 英文别名: tert-butyl N-[(2S,3S)-12-hydroxy-6-oxo-3-phenylmethoxydodecan-2-yl]carbamate
• CAS: 1175565-51-1
• 化学式: C₂₄H₃₉NO₅
• 分子量: 421.577
• InChiKey: YPDNQIFXBZUKGQ-UGKGYDQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl [(2S,3S)-3-benzyloxy-12-hydroxy-6-oxododecan-2-yl]carbamate 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 2.0h， 以89%的产率得到(10S,11S)-10-benzyloxy-11-(tert-butoxycarbonylamino)-7-oxododecanoic acid
  参考文献：
  名称：

  An enantioselective synthesis of (+)-azimic acid

  摘要：

  Herein we report a concise enantioselective synthesis of (+)-azimic acid starting from (5S,6S)-6-methyl-5-benzyloxy-2-piperidinone 8a, which was prepared from protected (S)-3-hydroxyglutarimide 6 according to a method recently disclosed in our laboratory. The key step is a stepwise regioselective reductive alkylation of the imide 10, which established the 2,6-cis-stereochemistry in excellent diastereoselectivity. (C) 2009 Elsevier Ltd. All Fights reserved.

  DOI：

  10.1016/j.tetasy.2009.04.008
• 作为产物：
  描述：

  tert-butyl [(2S,3S)-3-benzyloxy-12-(tert-butyldimethylsilyloxy)-6-oxododecan-2-yl]carbamate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到tert-butyl [(2S,3S)-3-benzyloxy-12-hydroxy-6-oxododecan-2-yl]carbamate
  参考文献：
  名称：

  An enantioselective synthesis of (+)-azimic acid

  摘要：

  Herein we report a concise enantioselective synthesis of (+)-azimic acid starting from (5S,6S)-6-methyl-5-benzyloxy-2-piperidinone 8a, which was prepared from protected (S)-3-hydroxyglutarimide 6 according to a method recently disclosed in our laboratory. The key step is a stepwise regioselective reductive alkylation of the imide 10, which established the 2,6-cis-stereochemistry in excellent diastereoselectivity. (C) 2009 Elsevier Ltd. All Fights reserved.

  DOI：

  10.1016/j.tetasy.2009.04.008

文献信息

• An enantioselective synthesis of (+)-azimic acid
  作者：Kai-Jiong Xiao、Liang-Xian Liu、Pei-Qiang Huang

  DOI：10.1016/j.tetasy.2009.04.008

  日期：2009.6

  Herein we report a concise enantioselective synthesis of (+)-azimic acid starting from (5S,6S)-6-methyl-5-benzyloxy-2-piperidinone 8a, which was prepared from protected (S)-3-hydroxyglutarimide 6 according to a method recently disclosed in our laboratory. The key step is a stepwise regioselective reductive alkylation of the imide 10, which established the 2,6-cis-stereochemistry in excellent diastereoselectivity. (C) 2009 Elsevier Ltd. All Fights reserved.