((1S,4S)-5-Azido-4-benzyloxy-1-hydroxymethyl-pentyl)-carbamic acid tert-butyl ester | 144090-62-0

• 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: ((1S,4S)-5-Azido-4-benzyloxy-1-hydroxymethyl-pentyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S,5S)-6-azido-1-hydroxy-5-phenylmethoxyhexan-2-yl]carbamate
• CAS: 144090-62-0
• 化学式: C₁₈H₂₈N₄O₄
• 分子量: 364.445
• InChiKey: DYDAZDRILJGFQP-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  82.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ((1S,4S)-5-Azido-4-benzyloxy-1-hydroxymethyl-pentyl)-carbamic acid tert-butyl ester 在 palladium dihydroxide 、 镍 jones reagent 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 silver(l) oxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 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-butoxycarbonyl-(4-methoxy-benzyl)-amino]-5-hydroxy-1-hydroxymethyl-pentyl ester 在 sodium azide 、 ammonium cerium(IV) nitrate 、 camphor-10-sulfonic acid 、 sodium methylate 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 氯化铵 、 对甲苯磺酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇甲醚 、 水 、 甲苯 、 乙腈 为溶剂， 生成 ((1S,4S)-5-Azido-4-benzyloxy-1-hydroxymethyl-pentyl)-carbamic acid tert-butyl 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

• Total synthesis and absolute configuration of bengamide A
  作者：Noritaka Chida、Takahiko Tobe、Shinsuke Okada、Seiichiro Ogawa

  DOI：10.1039/c39920001064

  日期：——

  The first total synthesis of the novel marine natural product, bengamide A 1 is described, revealing the absolute configuration of this compound.

  本论文描述了新型海洋天然产物孟加拉酰胺 A 1 的首次全合成，揭示了该化合物的绝对构型。
• 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.