2-benzoxazolyl 2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside | 1330533-84-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-benzoxazolyl 2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside
• 英文别名: (2S,4aR,6S,7R,8S,8aR)-6-(1,3-benzoxazol-2-ylsulfanyl)-2-phenyl-7-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 1330533-84-0
• 化学式: C₂₇H₂₅NO₆S
• 分子量: 491.565
• InChiKey: KMHVXCQHFJSYFL-OSZANLPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-thiazolinyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 、 2-benzoxazolyl 2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 在 溴甲苯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以77%的产率得到2-benzoxazolyl 2-O-benzyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-1-thio-β-D-galactopyranoside
  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：

  ethyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 在 溴 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成 2-benzoxazolyl 2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside
  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