benzyl 2-(3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-α-D-mannopyranosyl)-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside | 484647-55-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-(3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-α-D-mannopyranosyl)-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside
• 英文别名: benzyl N-[(1S)-1-[(2R,3R,4S,5R,6S)-5-[(2R,3S,4R,5R,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-4,5-bis(phenylmethoxy)oxan-2-yl]oxy-3,4,6-tris(phenylmethoxy)oxan-2-yl]-2-phenylmethoxyethyl]-N-methylcarbamate
• CAS: 484647-55-4
• 化学式: C₇₀H₈₃NO₁₃Si
• 分子量: 1174.51
• InChiKey: PEMHBRZMNLNMDQ-VKZZXWEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.62
• 重原子数：
  85
• 可旋转键数：
  30
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  benzyl 2-(3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-α-D-mannopyranosyl)-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside 在 草酰氯 、 TEA 、 二甲基亚砜 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以42.7 mg的产率得到benzyl 2-(3,4-di-O-benzyl-α-D-arabino-hexopyranos-2-ulos-1-yl)-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-L-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-(2-acetyl-3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-α-D-mannopyranosyl)-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-benzyloxycarbonylamino)-L-glycero-α-D-gluco-heptopyranoside 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以94%的产率得到benzyl 2-(3,4-di-O-benzyl-6-O-t-butyldimethylsilyl-α-D-mannopyranosyl)-3,4,7-tri-O-benzyl-6-deoxy-6-(N-methyl-N-benzyloxycarbonylamino)-L-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.