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 | 484647-54-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: [(2R,3S,4S,5R,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-[(2S,3R,4S,5R,6R)-6-[(1S)-1-[methyl(phenylmethoxycarbonyl)amino]-2-phenylmethoxyethyl]-2,4,5-tris(phenylmethoxy)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)oxan-3-yl] acetate
• CAS: 484647-54-3
• 化学式: C₇₂H₈₅NO₁₄Si
• 分子量: 1216.55
• InChiKey: NVQHWPZXBGXERZ-FLPAJSEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.19
• 重原子数：
  88
• 可旋转键数：
  32
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  148
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 在 咪唑 、 Dowex resin 、 三氟甲磺酸三甲基硅酯 、 四丁基碘化铵 、 sodium hydride 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 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
  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