2-amino-2-deoxy-α-D-galactopyranosyl-1-phosphoryl 2-acetamido-3,4-di-O-acetyl-6-O-[3,4,6-tri-Oacetyl-2-deoxy-2-(6-thioacetylhexanoyl)amino-β-D-glucopyranosyl]-2-deoxy-α-D-glucopyranoside | 1616559-59-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-2-deoxy-α-D-galactopyranosyl-1-phosphoryl 2-acetamido-3,4-di-O-acetyl-6-O-[3,4,6-tri-Oacetyl-2-deoxy-2-(6-thioacetylhexanoyl)amino-β-D-glucopyranosyl]-2-deoxy-α-D-glucopyranoside
• CAS: 1616559-59-1
• 化学式: C₃₈H₆₀N₃O₂₄PS
• 分子量: 1005.94
• InChiKey: SJGMSGKLZLMTOP-UYEGHSRISA-N

物化性质

• 密度：
  1.46±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.53
• 重原子数：
  67.0
• 可旋转键数：
  22.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  386.16
• 氢给体数：
  7.0
• 氢受体数：
  25.0

反应信息

• 作为反应物：
  描述：

  2-amino-2-deoxy-α-D-galactopyranosyl-1-phosphoryl 2-acetamido-3,4-di-O-acetyl-6-O-[3,4,6-tri-Oacetyl-2-deoxy-2-(6-thioacetylhexanoyl)amino-β-D-glucopyranosyl]-2-deoxy-α-D-glucopyranoside 在 羟胺 作用下， 以 甲醇 、 水 为溶剂， 反应 12.0h， 以3 mg的产率得到
  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：

  在 四氮唑 、 Sn(SPh)3•Et3N 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 氯仿 、 甲苯 、 乙腈 为溶剂， 反应 22.0h， 生成 2-amino-2-deoxy-α-D-galactopyranosyl-1-phosphoryl 2-acetamido-3,4-di-O-acetyl-6-O-[3,4,6-tri-Oacetyl-2-deoxy-2-(6-thioacetylhexanoyl)amino-β-D-glucopyranosyl]-2-deoxy-α-D-glucopyranoside
  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