N-Benzyl-2,2,2-trifluoro-N-[(S)-furan-2-yl-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methyl]-acetamide | 172847-78-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-Benzyl-2,2,2-trifluoro-N-[(S)-furan-2-yl-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methyl]-acetamide
• 英文别名: N-[(S)-[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-(furan-2-yl)methyl]-N-benzyl-2,2,2-trifluoroacetamide
• CAS: 172847-78-8
• 化学式: C₂₂H₂₄F₃NO₆
• 分子量: 455.431
• InChiKey: APGRATDIZXWDKC-FVVUREQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.4
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-Benzyl-2,2,2-trifluoro-N-[(S)-furan-2-yl-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methyl]-acetamide 在 盐酸 、 溶剂黄146 作用下， 反应 4.0h， 生成 N-Benzyl-N-[(S)-((2R,3S,4R,5R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-furan-2-yl-methyl]-2,2,2-trifluoro-acetamide
  参考文献：
  名称：

  Total synthesis of (+)-polyoxin J

  摘要：

  抗真菌抗生素聚氧菌素J1（46.4%）是通过将5-O-氨基甲酰聚氧胺酸2的受保护衍生物与胸腺嘧啶聚氧菌素C3偶联得到的，后者是通过糖醛（L-苏糖和二醛-D-呋喃核糖）的立体选择性氨基同源化策略制备的，其中使用硝酮4和5作为亚氨基衍生物，呋喃作为羧酸基团等价物。

  DOI：

  10.1039/c39950002127
• 作为产物：
  描述：

  (Z)-N-(5-deoxy-2,3-O-isopropylidene-1-O-methyl-β-D-ribo-1,4-furanose-5-ylidene)benzylamine N-oxide 在 copper diacetate 、 氯化二乙基铝 、 锌 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 6.0h， 生成 N-Benzyl-2,2,2-trifluoro-N-[(S)-furan-2-yl-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methyl]-acetamide
  参考文献：
  名称：

  Applications of Sugar Nitrones in Synthesis:  The Total Synthesis of (+)-Polyoxin J¹

  摘要：

  A convergent synthesis of the peptidyl nucleoside antibiotic (inhibitor of chitin biosynthesis) polyoxin J (2) by coupling of 5-O-carbamoyl polyoxamic acid (3) and thymine polyoxin C (4) is described. These compounds were prepared by chain elongation and amination of sugar-derived aldehydes employing their nitrones as iminium derivatives and the furan ring as a masked carboxyl. Thus, the stereoselective addition of 2-lithiofuran to the L-threose derived N-benzyl nitrone 5 followed by reduction of the resulting hydroxylamine to amine, carbamoylation of the free hydroxy group, and oxidative cleavage of the furan ring to the carboxylate group gave a protected derivative of 3 (30%). The same method was followed for the synthesis of the ribofuranosyl alpha-amino acid nucleoside 4 (12.6%) starting from the D-ribose derived nitrone 6. The final coupling was performed by the N-hydroxysuccinimide active ester method in DMSO with the Hunig base (i-Pr2EtNH) using a derivative of 3 and unprotected 4.

  DOI：

  10.1021/jo9702913

文献信息

• Applications of Sugar Nitrones in Synthesis:  The Total Synthesis of (+)-Polyoxin J¹
  作者：Alessandro Dondoni、Santiago Franco、Federico Junquera、Francisco L. Merchán、Pedro Merino、Tomás Tejero

  DOI：10.1021/jo9702913

  日期：1997.8.1

  A convergent synthesis of the peptidyl nucleoside antibiotic (inhibitor of chitin biosynthesis) polyoxin J (2) by coupling of 5-O-carbamoyl polyoxamic acid (3) and thymine polyoxin C (4) is described. These compounds were prepared by chain elongation and amination of sugar-derived aldehydes employing their nitrones as iminium derivatives and the furan ring as a masked carboxyl. Thus, the stereoselective addition of 2-lithiofuran to the L-threose derived N-benzyl nitrone 5 followed by reduction of the resulting hydroxylamine to amine, carbamoylation of the free hydroxy group, and oxidative cleavage of the furan ring to the carboxylate group gave a protected derivative of 3 (30%). The same method was followed for the synthesis of the ribofuranosyl alpha-amino acid nucleoside 4 (12.6%) starting from the D-ribose derived nitrone 6. The final coupling was performed by the N-hydroxysuccinimide active ester method in DMSO with the Hunig base (i-Pr2EtNH) using a derivative of 3 and unprotected 4.
• Total synthesis of (+)-polyoxin J
  作者：Alessandro Dondoni、Federico Junquera、Francisco L. Merchant、Pedro Merino、Tomas Tejero

  DOI：10.1039/c39950002127

  日期：——

  The antifungal antibiotic, polyoxin J 1, has been obtained (46.4%) by the coupling of a protected derivative of 5-O-carbamoylpolyoxamic acid 2 with thymine polyoxin C 3 which were prepared by a stereoselective aminohomologation strategy of sugar aldehydes (L-threose and dialdo-D-ribofuranose) employing nitrones 4 and 5 as their iminium derivatives and furan as a carboxylate group equivalent.

  抗真菌抗生素聚氧菌素J1（46.4%）是通过将5-O-氨基甲酰聚氧胺酸2的受保护衍生物与胸腺嘧啶聚氧菌素C3偶联得到的，后者是通过糖醛（L-苏糖和二醛-D-呋喃核糖）的立体选择性氨基同源化策略制备的，其中使用硝酮4和5作为亚氨基衍生物，呋喃作为羧酸基团等价物。