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 | 1616559-54-6

• 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-2-deoxy-6-O-[2-deoxy-2-hexanoylamino-β-D-glucopyranosyl]-α-D-glucopyranose
• 英文别名: [(2R,3R,4R,5S,6R)-3-acetamido-6-[[(2R,3R,4R,5S,6R)-3-(hexanoylamino)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4,5-dihydroxyoxan-2-yl] [(2R,3R,4R,5R,6R)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] hydrogen phosphate
• CAS: 1616559-54-6
• 化学式: C₂₆H₄₈N₃O₁₈P
• 分子量: 721.65
• InChiKey: MBCDCKISUBDFDO-AOVUZQMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -8.1
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  339
• 氢给体数：
  12
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  2-azido-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 作用下， 以 甲醇 为溶剂， 反应 24.0h， 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

文献信息

• Synthesis of Zwitterionic 1,1′-Glycosylphosphodiester: A Partial Structure of Galactosamine-Modified <i>Francisella</i> Lipid A
  作者：David Baum、Paul Kosma、Alla Zamyatina

  DOI：10.1021/ol501639c

  日期：2014.7.18

  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.