methyl (2R,3R,4S)-7-(benzyloxycarbonyl)amino-4-(diphenylmethylene)amino-2,3-O-isopropylidenedioxyheptanoate | 886230-84-8

• 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: methyl (2R,3R,4S)-7-(benzyloxycarbonyl)amino-4-(diphenylmethylene)amino-2,3-O-isopropylidenedioxyheptanoate
• 英文别名: methyl (4R,5R)-5-[(1S)-1-(benzhydrylideneamino)-4-(phenylmethoxycarbonylamino)butyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate
• CAS: 886230-84-8
• 化学式: C₃₂H₃₆N₂O₆
• 分子量: 544.648
• InChiKey: RZDNYOYQQZJAAV-WIIGKZCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  95.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2R,3R,4S)-7-(benzyloxycarbonyl)amino-4-(diphenylmethylene)amino-2,3-O-isopropylidenedioxyheptanoate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 甲酸铵 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 25.0h， 生成 (3R,4R,5S)-5-(3-(tert-butoxycarbonyl)amino)propyl-3,4-O-isopropylidenedioxypyrrolidin-2-one
  参考文献：
  名称：

  Stereoselective Synthesis of Protected (2R,3R,4S)-4,7-Diamino-2,3-dihydroxyheptanoic Acid:  A Novel Amino Acid of Callipeltins A and D

  摘要：

  An orthogonally protected derivative 1 of (2R,3R,4S)-4,7diamino-2,3-dihydroxyheptanoic acid, the unusual amino acid residue of the biologically active marine peptides such as callipeltins A and D and neamphamide A, was efficiently prepared in 10 steps and 30% overall yield from a commercially available L-ornithine derivative 2. The key step includes the N-diphenyl methylene-control led diastereoselective dihydroxylation of (Z)-ester 3 with > 13:1 selectivity for the desired isomer.

  DOI：

  10.1021/jo052676o
• 作为产物：
  描述：

  (S)-4-(Benzhydrylidene-amino)-7-benzyloxycarbonylamino-2,3-dihydroxy-heptanoic acid methyl ester 、 2,2-二甲氧基丙烷 在 4-甲基苯磺酸吡啶 作用下， 以 苯 为溶剂， 反应 3.0h， 以75%的产率得到methyl (2R,3R,4S)-7-(benzyloxycarbonyl)amino-4-(diphenylmethylene)amino-2,3-O-isopropylidenedioxyheptanoate
  参考文献：
  名称：

  Stereoselective Synthesis of Protected (2R,3R,4S)-4,7-Diamino-2,3-dihydroxyheptanoic Acid:  A Novel Amino Acid of Callipeltins A and D

  摘要：

  An orthogonally protected derivative 1 of (2R,3R,4S)-4,7diamino-2,3-dihydroxyheptanoic acid, the unusual amino acid residue of the biologically active marine peptides such as callipeltins A and D and neamphamide A, was efficiently prepared in 10 steps and 30% overall yield from a commercially available L-ornithine derivative 2. The key step includes the N-diphenyl methylene-control led diastereoselective dihydroxylation of (Z)-ester 3 with > 13:1 selectivity for the desired isomer.

  DOI：

  10.1021/jo052676o