benzyl 3,4,7-tri-O-benzyl-2-O-(p-methoxybenzyl)-L-glycero-α-D-glucoheptopyranoside | 484647-64-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 3,4,7-tri-O-benzyl-2-O-(p-methoxybenzyl)-L-glycero-α-D-glucoheptopyranoside
• 英文别名: Mob(-2)[Bn(-3)][Bn(-4)][Bn(-7)]L-gro-D-glcHept(a)-O-Bn；(1S)-1-[(2R,3S,4S,5R,6S)-5-[(4-methoxyphenyl)methoxy]-3,4,6-tris(phenylmethoxy)oxan-2-yl]-2-phenylmethoxyethanol
• CAS: 484647-64-5
• 化学式: C₄₃H₄₆O₈
• 分子量: 690.833
• InChiKey: ASBJKAMPDILYQM-RHEHPOLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  51
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl 3,4,7-tri-O-benzyl-2-O-(p-methoxybenzyl)-L-glycero-α-D-glucoheptopyranoside 在 二苯基膦叠氮化物 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以89%的产率得到(2R,3R,4S,5R,6S)-2-((R)-1-Azido-2-benzyloxy-ethyl)-3,4,6-tris-benzyloxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran
  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 3,4,7-tri-O-benzyl-2-O-(p-methoxybenzyl)-(L/D)-glycero-α-D-glucoheptopyranoside 在 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 7.0h， 生成 benzyl 3,4,7-tri-O-benzyl-2-O-(p-methoxybenzyl)-L-glycero-α-D-glucoheptopyranoside
  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.