ethyl 2-azido-4,6-O-di-tert-butylsilylene-2-deoxy-1-thio-α-D-galactopyranoside | 1616559-34-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-azido-4,6-O-di-tert-butylsilylene-2-deoxy-1-thio-α-D-galactopyranoside
• CAS: 1616559-34-2
• 化学式: C₁₆H₃₁N₃O₄SSi
• 分子量: 389.591
• InChiKey: BMMWGAVVDDGXHK-XGFWRYKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  96.68
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  ethyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thio-D-galactopyranoside 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.25h， 生成 ethyl 2-azido-4,6-O-di-tert-butylsilylene-2-deoxy-1-thio-α-D-galactopyranoside 、 ethyl 2-azido-4,6-O-di-tert-butylsilylene-2-deoxy-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Zwitterionic 1,1′-Glycosylphosphodiester: A Partial Structure of Galactosamine-Modified Francisella Lipid A

  摘要：

  Synthesis of a "double glycosidic" phosphodiester comprising anomeric centers of two 2-amino-2-deoxy-sugars is reported. The carbohydrate epitope of Francisella lipid A modified with alpha-D-galactosamine at the anomerically linked phosphate has been stereoselectively prepared and coupled to maleimide-activated bovine serum albumin via an amide-linked thiol-terminated spacer group. H-Phosphonate and phosphoramidite approaches have been explored for the coupling of 4,6-DTBS-2-azido-protected GalN lactol and peracetylated spacer-equipped reducing beta GlcN(1 -> 6)GlcN disaccharide via phosphodiester linkage. Deprotection conditions preserving the integrity of the labile glycosidic zwitterionic phosphodiester were elaborated.

  DOI：

  10.1021/ol501639c