benzyl 3-O-benzyl-4,6-O-benzylidene-2-O-(p-toluenesulfonyl)-α-D-glucopyranoside | 484647-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 3-O-benzyl-4,6-O-benzylidene-2-O-(p-toluenesulfonyl)-α-D-glucopyranoside
• 英文别名: [(2R,4aR,6S,7R,8S,8aR)-2-phenyl-6,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl] 4-methylbenzenesulfonate
• CAS: 484647-44-1
• 化学式: C₃₄H₃₄O₈S
• 分子量: 602.705
• InChiKey: GUCPVGLVCNYPRN-GPYWBMRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl 3-O-benzyl-4,6-O-benzylidene-2-O-(p-toluenesulfonyl)-α-D-glucopyranoside 在 sodium tetrahydroborate 作用下， 以 二甲基亚砜 为溶剂， 反应 20.0h， 以82%的产率得到benzyl 3-O-benzyl-4,6-O-benzylidene-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
• 作为产物：
  描述：

  benzyl 4,6-O-benzylidene-α-D-glucopyranoside 在 barium dihydroxide 、 二正丁基氧化锡 、 barium(II) oxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 13.0h， 生成 benzyl 3-O-benzyl-4,6-O-benzylidene-2-O-(p-toluenesulfonyl)-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.