benzyl [3,4-di-O-benzyl-6-O-(3-hydroxycarbonylpropanoyl)-α-D-mannopyranosyl]-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-D-glycero-α-D-gluco-heptopyranoside | 484647-73-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: benzyl [3,4-di-O-benzyl-6-O-(3-hydroxycarbonylpropanoyl)-α-D-mannopyranosyl]-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-D-glycero-α-D-gluco-heptopyranoside
• 英文别名: 4-[[(2R,3R,4R,5S,6R)-5-hydroxy-6-[(2S,3R,4S,5R,6R)-6-[(1R)-1-[methyl(phenylmethoxycarbonyl)amino]-2-phenylmethoxyethyl]-2,4,5-tris(phenylmethoxy)oxan-3-yl]oxy-3,4-bis(phenylmethoxy)oxan-2-yl]methoxy]-4-oxobutanoic acid
• CAS: 484647-73-6
• 化学式: C₆₈H₇₃NO₁₆
• 分子量: 1160.32
• InChiKey: CYEFNTXKVUZMIR-VRBJKSFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  85
• 可旋转键数：
  32
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  196
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  1,6,17,29-tetrakis(benzyloxy)-7,10,18,21-tetraoxo-6,11,17,22,28-pentaazaoctacosane 、 benzyl [3,4-di-O-benzyl-6-O-(3-hydroxycarbonylpropanoyl)-α-D-mannopyranosyl]-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-D-glycero-α-D-gluco-heptopyranoside 在 N-羟基-7-氮杂苯并三氮唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以94%的产率得到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-di-O-benzyl-D-glycero-α-D-gluco-heptopyranoside
  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 2-[3,4-di-O-benzyl-6-O-(3-hydroxycarbonylpropanoyl)-2-O-(p-methoxybenzyl)-α-D-mannopyranosyl]-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-D-glycero-α-D-gluco-heptopyranoside 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 以81%的产率得到benzyl [3,4-di-O-benzyl-6-O-(3-hydroxycarbonylpropanoyl)-α-D-mannopyranosyl]-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-D-glycero-α-D-gluco-heptopyranoside
  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.