(2S,5S)-6-Azido-5-benzyloxy-2-tert-butoxycarbonylamino-hexanoic acid pentafluorophenyl ester | 163072-67-1

• 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,5S)-6-Azido-5-benzyloxy-2-tert-butoxycarbonylamino-hexanoic acid pentafluorophenyl ester
• 英文别名: (2,3,4,5,6-pentafluorophenyl) (2S,5S)-6-azido-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylmethoxyhexanoate
• CAS: 163072-67-1
• 化学式: C₂₄H₂₅F₅N₄O₅
• 分子量: 544.478
• InChiKey: AOQQNQFFICPFMR-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  88.2
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2S,5S)-6-Azido-5-benzyloxy-2-tert-butoxycarbonylamino-hexanoic acid pentafluorophenyl ester 在 palladium dihydroxide 、 镍 氢气 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3S,6S)-1-methyl-3-(tert-butyloxycarbonyl)aminohexahydro-6-hydroxy-2H-azepin-2-one
  参考文献：
  名称：

  Stereoselective Conversion of L-Quebrachitol into a Novel Hydroxylated Caprolactam: Total Synthesis of Bengamide B

  摘要：

  The stereoselective synthesis of the novel marine natural product, bengamide B (1), starting from L-quebrachitol (3) is described. The hydroxylated caprolactam portion (2a) in 1 was prepared from (+)-conduramine derivative (7), whose amino functionality was introduced stereoselectively by means of palladium-catalyzed azidation of a chiral cyclohexene (6) derived from 3.

  DOI：

  10.3987/com-94-6869
• 作为产物：
  描述：

  Benzoic acid (1S,4S)-4-tert-butoxycarbonylamino-5-hydroxy-1-hydroxymethyl-pentyl ester 在 sodium azide 、 jones reagent 、 camphor-10-sulfonic acid 、 sodium methylate 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 氯化铵 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙二醇甲醚 、 水 、 丙酮 、 甲苯 为溶剂， 生成 (2S,5S)-6-Azido-5-benzyloxy-2-tert-butoxycarbonylamino-hexanoic acid pentafluorophenyl ester
  参考文献：
  名称：

  Stereoselective Conversion of L-Quebrachitol into a Novel Hydroxylated Caprolactam: Total Synthesis of Bengamide B

  摘要：

  The stereoselective synthesis of the novel marine natural product, bengamide B (1), starting from L-quebrachitol (3) is described. The hydroxylated caprolactam portion (2a) in 1 was prepared from (+)-conduramine derivative (7), whose amino functionality was introduced stereoselectively by means of palladium-catalyzed azidation of a chiral cyclohexene (6) derived from 3.

  DOI：

  10.3987/com-94-6869

文献信息

• Stereoselective Conversion of L-Quebrachitol into a Novel Hydroxylated Caprolactam: Total Synthesis of Bengamide B
  作者：Noritaka Chida、Takahiko Tobe、Katsuyuki Murai、Kaori Yamazaki、Seiichiro Ogawa

  DOI：10.3987/com-94-6869

  日期：——

  The stereoselective synthesis of the novel marine natural product, bengamide B (1), starting from L-quebrachitol (3) is described. The hydroxylated caprolactam portion (2a) in 1 was prepared from (+)-conduramine derivative (7), whose amino functionality was introduced stereoselectively by means of palladium-catalyzed azidation of a chiral cyclohexene (6) derived from 3.