4-[5-[[1-hydroxy-4-oxo-4-[phenylmethoxy(5-phenylmethoxypentyl)amino]butylidene]amino]pentyl-phenylmethoxyamino]-N-[5-[[4-[[(2R,3R,4S,6R)-6-[(2S,3R,4S,5R,6R)-6-[(1S)-1-[methyl(phenylmethoxycarbonyl)amino]-2-phenylmethoxyethyl]-2,4,5-tris(phenylmethoxy)oxan-3-yl]oxy-5-oxo-3,4-bis(phenylmethoxy)oxan-2-yl]methoxy]-4-oxobutanoyl]-phenylmethoxyamino]pentyl]-4-oxobutanimidic acid | 484647-63-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[5-[[1-hydroxy-4-oxo-4-[phenylmethoxy(5-phenylmethoxypentyl)amino]butylidene]amino]pentyl-phenylmethoxyamino]-N-[5-[[4-[[(2R,3R,4S,6R)-6-[(2S,3R,4S,5R,6R)-6-[(1S)-1-[methyl(phenylmethoxycarbonyl)amino]-2-phenylmethoxyethyl]-2,4,5-tris(phenylmethoxy)oxan-3-yl]oxy-5-oxo-3,4-bis(phenylmethoxy)oxan-2-yl]methoxy]-4-oxobutanoyl]-phenylmethoxyamino]pentyl]-4-oxobutanimidic acid
• CAS: 484647-63-4
• 化学式: C₁₁₉H₁₃₈N₆O₂₃
• 分子量: 2020.43
• InChiKey: GRCWBUAOLOEMPG-JHVILHPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16
• 重原子数：
  148
• 可旋转键数：
  67
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  319
• 氢给体数：
  2
• 氢受体数：
  25

反应信息

• 作为反应物：
  描述：

  4-[5-[[1-hydroxy-4-oxo-4-[phenylmethoxy(5-phenylmethoxypentyl)amino]butylidene]amino]pentyl-phenylmethoxyamino]-N-[5-[[4-[[(2R,3R,4S,6R)-6-[(2S,3R,4S,5R,6R)-6-[(1S)-1-[methyl(phenylmethoxycarbonyl)amino]-2-phenylmethoxyethyl]-2,4,5-tris(phenylmethoxy)oxan-3-yl]oxy-5-oxo-3,4-bis(phenylmethoxy)oxan-2-yl]methoxy]-4-oxobutanoyl]-phenylmethoxyamino]pentyl]-4-oxobutanimidic acid 在 钯 高氯酸 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 以34%的产率得到6-deoxy-6-methylamino-2-O-[6-O-(5,16,27,32-tetrahydroxy-1,4,12,15,23,26-hexaoxo-5,11,16,22,27-pentaazadotriacont-1-yl)-α-D-arabino-hexopyranos-2-ulos-1-yl]-L-glycero-D-gluco-heptopyranose
  参考文献：
  名称：

  Total Synthesis of Desferrisalmycin B

  摘要：

  The first total synthesis of a naturally occurring siderophore antibiotic, desferrisalmycin B, is described, and the configuration of the unknown stereocenter is assigned. The synthesis features a synthetic strategy of constructing the novel amino-heptopyranoside component by stereoselective dihydroxylation followed by a Bose-modified Mitsunobu reaction. Through this convergent approach, other members of salmycins should also be synthetically accessible.

  DOI：

  10.1021/ja028386w
• 作为产物：
  描述：

  benzyl 6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-2-O-[3,4-di-O-benzyl-6-O-(5,16,27,32-tetrabenzyloxy-1,4,12,15,23,26-hexaoxo-5,11,16,22,27-pentaazadotricont-1-yl)-α-D-mannopyranosyl]-3,4-di0O-benzyl-L-glycero-α-D-gluco-heptopyranoside 在 草酰氯 、 TEA 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到4-[5-[[1-hydroxy-4-oxo-4-[phenylmethoxy(5-phenylmethoxypentyl)amino]butylidene]amino]pentyl-phenylmethoxyamino]-N-[5-[[4-[[(2R,3R,4S,6R)-6-[(2S,3R,4S,5R,6R)-6-[(1S)-1-[methyl(phenylmethoxycarbonyl)amino]-2-phenylmethoxyethyl]-2,4,5-tris(phenylmethoxy)oxan-3-yl]oxy-5-oxo-3,4-bis(phenylmethoxy)oxan-2-yl]methoxy]-4-oxobutanoyl]-phenylmethoxyamino]pentyl]-4-oxobutanimidic acid
  参考文献：
  名称：

  Total Synthesis of Desferrisalmycin B

  摘要：

  The first total synthesis of a naturally occurring siderophore antibiotic, desferrisalmycin B, is described, and the configuration of the unknown stereocenter is assigned. The synthesis features a synthetic strategy of constructing the novel amino-heptopyranoside component by stereoselective dihydroxylation followed by a Bose-modified Mitsunobu reaction. Through this convergent approach, other members of salmycins should also be synthetically accessible.

  DOI：

  10.1021/ja028386w

文献信息

• Total Synthesis of Desferrisalmycin B
  作者：Li Dong、John M. Roosenberg、Marvin J. Miller

  DOI：10.1021/ja028386w

  日期：2002.12.1

  The first total synthesis of a naturally occurring siderophore antibiotic, desferrisalmycin B, is described, and the configuration of the unknown stereocenter is assigned. The synthesis features a synthetic strategy of constructing the novel amino-heptopyranoside component by stereoselective dihydroxylation followed by a Bose-modified Mitsunobu reaction. Through this convergent approach, other members of salmycins should also be synthetically accessible.