methyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside | 1220286-27-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside
• CAS: 1220286-27-0
• 化学式: C₄₈H₅₂O₁₀
• 分子量: 788.935
• InChiKey: WBXBYWXTUSCSJR-DIWLKYFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.94
• 重原子数：
  58.0
• 可旋转键数：
  16.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  92.3
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  methyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 在 HClO₄-SiO₂ 作用下， 以 水 、 乙腈 为溶剂， 反应 0.33h， 以79%的产率得到methyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Tri- and Disaccharide Fragments Related to the O-Antigen of Enteropathogenic Escherichia Coli O158

  摘要：

  Chemical synthesis of a tri- and a disaccharide related to the O-antigen of enteropathogenic E. coli O158 was achieved in high yield. In the disaccharide (2), one D-galactosamine unit is present in 1,2-cis-linked and the other is in the trans-orientation, and both of them were prepared from the same intermediate by tuning the reaction solvent. Yields were considerably high in all steps.

  DOI：

  10.1080/07328300903477804
• 作为产物：
  描述：

  methyl 2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 四丁基溴化铵 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 methyl (2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Tri- and Disaccharide Fragments Related to the O-Antigen of Enteropathogenic Escherichia Coli O158

  摘要：

  Chemical synthesis of a tri- and a disaccharide related to the O-antigen of enteropathogenic E. coli O158 was achieved in high yield. In the disaccharide (2), one D-galactosamine unit is present in 1,2-cis-linked and the other is in the trans-orientation, and both of them were prepared from the same intermediate by tuning the reaction solvent. Yields were considerably high in all steps.

  DOI：

  10.1080/07328300903477804

文献信息

• Stereoselective β-mannosylations and β-rhamnosylations from glycosyl hemiacetals mediated by lithium iodide
  作者：Imlirenla Pongener、Dionissia A. Pepe、Joseph J. Ruddy、Eoghan M. McGarrigle

  DOI：10.1039/d1sc01300a

  日期：——

  Stereoselective β-mannosylation is one of the most challenging problems in the synthesis of oligosaccharides. Herein, a highly selective synthesis of β-mannosides and β-rhamnosides from glycosyl hemi-acetals is reported, following a one-pot chlorination, iodination, glycosylation sequence employing cheap oxalyl chloride, phosphine oxide and LiI. The present protocol works excellently with a wide range

  立体选择性β-甘露糖基化是寡糖合成中最具挑战性的问题之一。在此，报道了使用廉价的草酰氯、氧化膦和 LiI 进行一锅氯化、碘化、糖基化序列后，从糖基半缩醛中高度选择性地合成 β-甘露糖苷和 β-鼠李糖苷。本协议适用于广泛的糖基受体和武装糖基供体。该方法不需要构象限制的供体或导向基团；建议观察到的高β-选择性是通过碘化锂促进的 α-糖基碘化物的 S N 2 型反应实现的。