N-((R)-1-tert-Butylcarbamoyl-3-methyl-butyl)-N-((2R,3R,4S,5S)-3,4,5-trihydroxy-tetrahydro-thiopyran-2-yl)-benzamide | 417707-04-1

• 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: N-((R)-1-tert-Butylcarbamoyl-3-methyl-butyl)-N-((2R,3R,4S,5S)-3,4,5-trihydroxy-tetrahydro-thiopyran-2-yl)-benzamide
• 英文别名: N-[(2R)-1-(tert-butylamino)-4-methyl-1-oxopentan-2-yl]-N-[(2R,3R,4S,5S)-3,4,5-trihydroxythian-2-yl]benzamide
• CAS: 417707-04-1
• 化学式: C₂₂H₃₄N₂O₅S
• 分子量: 438.588
• InChiKey: KVLASAWFGVAVGA-ZIKOTGLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  110.1
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-((R)-1-tert-Butylcarbamoyl-3-methyl-butyl)-N-((2R,3R,4S,5S)-3,4,5-trihydroxy-tetrahydro-thiopyran-2-yl)-benzamide 在 mercury(II) diacetate 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以60%的产率得到N-((R)-1-tert-Butylcarbamoyl-3-methyl-butyl)-benzamide
  参考文献：
  名称：

  Stereoselective syntheses of α-amino acid and peptide derivatives by the U-4CR of 5-desoxy-5-thio-<small>D</small>-xylopyranosylamine

  摘要：

  Since 1961, the synthesis of alpha-amino acids derivatives by the four-component reaction of isocyanides (U-4CR) as a one-pot reaction has been developed. Only recently it was found that a variety of these cc-amino acids compounds can be formed stereoselectively by the U-4CR using 1-amino-5-deoxy-5-thio-2,3,4-tri-O-isobutanoyl-beta-D-xylopyranose as the amine component. The stereoselectivity inducing auxiliary 5-desoxy-5-thio-D-xylopyranosyl group of the so-formed products can be replaced selectively by hydrogen.

  DOI：

  10.1139/cjc-79-12-1934
• 作为产物：
  描述：

  2,3,4-tri-O-isobutanoyl-5-desoxy-5-thio-β-D-xylopyranosylamine 在 zinc chloride diethyl ether 、 magnesium sulfate 、 三乙胺 、 甲胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 110.0h， 生成 N-((R)-1-tert-Butylcarbamoyl-3-methyl-butyl)-N-((2R,3R,4S,5S)-3,4,5-trihydroxy-tetrahydro-thiopyran-2-yl)-benzamide
  参考文献：
  名称：

  Stereoselective syntheses of α-amino acid and peptide derivatives by the U-4CR of 5-desoxy-5-thio-<small>D</small>-xylopyranosylamine

  摘要：

  Since 1961, the synthesis of alpha-amino acids derivatives by the four-component reaction of isocyanides (U-4CR) as a one-pot reaction has been developed. Only recently it was found that a variety of these cc-amino acids compounds can be formed stereoselectively by the U-4CR using 1-amino-5-deoxy-5-thio-2,3,4-tri-O-isobutanoyl-beta-D-xylopyranose as the amine component. The stereoselectivity inducing auxiliary 5-desoxy-5-thio-D-xylopyranosyl group of the so-formed products can be replaced selectively by hydrogen.

  DOI：

  10.1139/cjc-79-12-1934