2-azido-3-O-tert-butyldimethylsilyl-4,6-O-di-tert-butylsilylene-2-deoxy-α-D-galactopyranosyl-1-phosphoryl 2-acetamido-3,4-di-O-acetyl-6-O-[3,4,6-tri-O-acetyl-2-deoxy-2-hexanoylamino-β-D-glucopyranosyl]-2-deoxy-α-D-glucopyranose (ammonium salt) | 1616559-50-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azido-3-O-tert-butyldimethylsilyl-4,6-O-di-tert-butylsilylene-2-deoxy-α-D-galactopyranosyl-1-phosphoryl 2-acetamido-3,4-di-O-acetyl-6-O-[3,4,6-tri-O-acetyl-2-deoxy-2-hexanoylamino-β-D-glucopyranosyl]-2-deoxy-α-D-glucopyranose (ammonium salt)
• CAS: 1616559-50-2
• 化学式: C₅₀H₈₆N₅O₂₃PSi₂*H₃N
• 分子量: 1229.43
• InChiKey: DBPXFRLJCDCRAG-GZMJYHLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.86
• 重原子数：
  82.0
• 可旋转键数：
  22.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  393.83
• 氢给体数：
  4.0
• 氢受体数：
  24.0

反应信息

• 作为反应物：
  描述：

  2-azido-3-O-tert-butyldimethylsilyl-4,6-O-di-tert-butylsilylene-2-deoxy-α-D-galactopyranosyl-1-phosphoryl 2-acetamido-3,4-di-O-acetyl-6-O-[3,4,6-tri-O-acetyl-2-deoxy-2-hexanoylamino-β-D-glucopyranosyl]-2-deoxy-α-D-glucopyranose (ammonium salt) 在 palladium on activated charcoal 、 水 、 氢气 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 为溶剂， 反应 25.0h， 生成 2-amino-2-deoxy-α-D-galactopyranosyl-1-phosphoryl 2-acetamido-2-deoxy-6-O-[2-deoxy-2-hexanoylamino-β-D-glucopyranosyl]-α-D-glucopyranose
  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
• 作为产物：
  描述：

  2-azido-3-O-tert-butyldimethylsilyl-4,6-O-di-tert-butylsilylene-2-deoxy-D-galactopyranosyl-1-hydrogenphosphonate (ammonium salt) 、 2-acetamido-3,4-di-O-acetyl-6-O-[3,4,6-tri-O-acetyl-2-deoxy-2-hexanoylamino-β-D-glucopyranosyl]-2-deoxy-D-glucopyranoside 在 碘 作用下， 以 二氯甲烷 、 吡啶 、 水 为溶剂， 反应 3.33h， 以53%的产率得到2-azido-3-O-tert-butyldimethylsilyl-4,6-O-di-tert-butylsilylene-2-deoxy-α-D-galactopyranosyl-1-phosphoryl 2-acetamido-3,4-di-O-acetyl-6-O-[3,4,6-tri-O-acetyl-2-deoxy-2-hexanoylamino-β-D-glucopyranosyl]-2-deoxy-α-D-glucopyranose (ammonium salt)
  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