methyl 5-(acetoxyamino)-N-benzyl-5-deoxy-2,3-isopropylidene-5-(2-furyl)-β-D-allo-1,4-pentofuranoside | 191997-67-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-(acetoxyamino)-N-benzyl-5-deoxy-2,3-isopropylidene-5-(2-furyl)-β-D-allo-1,4-pentofuranoside
• 英文别名: [[(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]-benzylamino] acetate
• CAS: 191997-67-8
• 化学式: C₂₂H₂₇NO₇
• 分子量: 417.459
• InChiKey: LSVASHGSJPNSTH-PFAUGDHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl 5-(acetoxyamino)-N-benzyl-5-deoxy-2,3-isopropylidene-5-(2-furyl)-β-D-allo-1,4-pentofuranoside 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 4.0h， 以36%的产率得到5-(acetoxyamino)-N-benzyl-5-deoxy-5-(2-furyl)-1,2,3-tri-O-acetyl-β-D-allo-1,4-pentofuranoside
  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
• 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 4-二甲氨基吡啶 、 氯化二乙基铝 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 正己烷 为溶剂， 反应 4.0h， 生成 methyl 5-(acetoxyamino)-N-benzyl-5-deoxy-2,3-isopropylidene-5-(2-furyl)-β-D-allo-1,4-pentofuranoside
  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