benzyl 6-azido-3,4,7-tri-O-benzyl-6-deoxy-2-O-(p-methoxybenzyl)-L-glycero-α-D-glucopyranoside | 484647-50-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 6-azido-3,4,7-tri-O-benzyl-6-deoxy-2-O-(p-methoxybenzyl)-L-glycero-α-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-2-[(1S)-1-azido-2-phenylmethoxyethyl]-5-[(4-methoxyphenyl)methoxy]-3,4,6-tris(phenylmethoxy)oxane
• CAS: 484647-50-9
• 化学式: C₄₃H₄₅N₃O₇
• 分子量: 715.846
• InChiKey: WANQFPRPCNPDLC-RHEHPOLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  53
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  79
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  benzyl 6-azido-3,4,7-tri-O-benzyl-6-deoxy-2-O-(p-methoxybenzyl)-L-glycero-α-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 、 TEA 、 sodium hydride 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 9.5h， 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
• 作为产物：
  描述：

  benzyl 3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-D-gluco-heptopyranoside 在 二苯基膦叠氮化物 、 二正丁基氧化锡 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 5.0h， 生成 benzyl 6-azido-3,4,7-tri-O-benzyl-6-deoxy-2-O-(p-methoxybenzyl)-L-glycero-α-D-glucopyranoside
  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.