allyl 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-glucopyranoside | 1616559-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 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-glucopyranoside
• CAS: 1616559-46-6
• 化学式: C₃₃H₅₀N₂O₁₆
• 分子量: 730.764
• InChiKey: CPRMQDVAMZONMV-FBCKYRCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.52
• 重原子数：
  51.0
• 可旋转键数：
  18.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  226.62
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  allyl 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-glucopyranoside 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 、 碘 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以41.176%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：

  allyl 2-acetamido-3,4-di-O-acetyl-6-O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-2-deoxy-α-D-glucopyranoside 、 己酸 在 锌 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以76.8%的产率得到allyl 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-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