2-benzoxazolyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside | 1117896-30-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-benzoxazolyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-6-[[(2R,3R,4S,5R,6R)-6-[[(2R,3R,4S,5R,6S)-6-(1,3-benzoxazol-2-ylsulfanyl)-3,4,5-tribenzoyloxyoxan-2-yl]methoxy]-3,4,5-tribenzoyloxyoxan-2-yl]methoxy]-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 1117896-30-6
• 化学式: C₉₅H₇₅NO₂₆S
• 分子量: 1678.7
• InChiKey: NMVOROBXNKZHDC-SGLLRROVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18
• 重原子数：
  123
• 可旋转键数：
  39
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  361
• 氢给体数：
  0
• 氢受体数：
  28

反应信息

• 作为反应物：
  描述：

  2-benzoxazolyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 、 2,3,4-tri-O-benzoyl-β-D-glucopyranosyl fluoride 在 三氟甲烷磺酸甲酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以87%的产率得到O-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl fluoride
  参考文献：
  名称：

  On Orthogonal and Selective Activation of Glycosyl Thioimidates and Thioglycosides: Application to Oligosaccharide Assembly

  摘要：

  Discrimination among S-thiazolinyl (STaz), S-benzoxazolyl (SBox), and S-ethyl anomeric leaving groups was achieved by fine-tuning activation conditions. Preferential glycosidation of a certain leaving group is determined neither by the strength of the activating reagent nor by the stability of the leaving group itself; instead, the type of activation plays the key role. The activation conditions established herein were applied to a sequential five-step synthesis of a hexasaccharide using six monosaccharide building blocks equipped with six different leaving groups.

  DOI：

  10.1021/jo201117s
• 作为产物：
  描述：

  benzoxazol-2-yl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside 、 2-thiazolinyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 在 溴甲苯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 73.0h， 以67%的产率得到2-benzoxazolyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  On Orthogonal and Selective Activation of Glycosyl Thioimidates and Thioglycosides: Application to Oligosaccharide Assembly

  摘要：

  Discrimination among S-thiazolinyl (STaz), S-benzoxazolyl (SBox), and S-ethyl anomeric leaving groups was achieved by fine-tuning activation conditions. Preferential glycosidation of a certain leaving group is determined neither by the strength of the activating reagent nor by the stability of the leaving group itself; instead, the type of activation plays the key role. The activation conditions established herein were applied to a sequential five-step synthesis of a hexasaccharide using six monosaccharide building blocks equipped with six different leaving groups.

  DOI：

  10.1021/jo201117s

文献信息

• On Orthogonal and Selective Activation of Glycosyl Thioimidates and Thioglycosides: Application to Oligosaccharide Assembly
  作者：Sophon Kaeothip、Alexei V. Demchenko

  DOI：10.1021/jo201117s

  日期：2011.9.16

  Discrimination among S-thiazolinyl (STaz), S-benzoxazolyl (SBox), and S-ethyl anomeric leaving groups was achieved by fine-tuning activation conditions. Preferential glycosidation of a certain leaving group is determined neither by the strength of the activating reagent nor by the stability of the leaving group itself; instead, the type of activation plays the key role. The activation conditions established herein were applied to a sequential five-step synthesis of a hexasaccharide using six monosaccharide building blocks equipped with six different leaving groups.