benzyl 3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-D-glucopiranoside | 484647-46-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-D-glucopiranoside
• 英文别名: [(2R,3R,4S,5R,6S)-5-[(4-methoxyphenyl)methoxy]-3,4,6-tris(phenylmethoxy)oxan-2-yl]methanol
• CAS: 484647-46-3
• 化学式: C₃₅H₃₈O₇
• 分子量: 570.683
• InChiKey: CDQKQHADLOYLFQ-KJQSSVQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl 3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-D-glucopiranoside 在 草酰氯 、 TEA 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3S,4S,5R,6S)-5-[(4-methoxyphenyl)methoxy]-3,4,6-tris(phenylmethoxy)oxane-2-carbaldehyde
  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 4,6-O-benzylidene-2-O-(p-toluenesulfonyl)-α-D-glucopyranoside 在 barium dihydroxide 、 sodium tetrahydroborate 、 硼烷四氢呋喃络合物 、 三氟甲磺酸二丁硼 、 四丁基溴化铵 、 sodium hydride 、 barium(II) oxide 作用下， 以 四氢呋喃 、 乙醚 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 benzyl 3,4-di-O-benzyl-2-O-(p-methoxybenzyl)-α-D-glucopiranoside
  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.