octyl 2,4,6-tri-O-benzyl-3-O-diphenoxyphosphono-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside | 503602-50-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: octyl 2,4,6-tri-O-benzyl-3-O-diphenoxyphosphono-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS: 503602-50-4
• 化学式: C₆₉H₈₀NO₁₄P
• 分子量: 1178.37
• InChiKey: JOJOEWVCBMMUNC-KFUXMZKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.54
• 重原子数：
  85.0
• 可旋转键数：
  34.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  156.93
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  octyl 2,4,6-tri-O-benzyl-3-O-diphenoxyphosphono-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 在 palladium on activated charcoal 、 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 反应 30.0h， 以56%的产率得到octyl 3-O-phosphono-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside disodium salt
  参考文献：
  名称：

  Synthesis and NMR characterization of the six regioisomeric monophosphates of octyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside

  摘要：

  All six regioisomeric monophosphates of octyl beta-D-galactopyranosyl-(1 --> 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside have been chemically synthesized and characterized by high-resolution H-1, C-13 and P-31 NMR spectroscopy. Phosphorylation causes characteristic downfield shifts of the nucleus at the substituted site in the H-1 and C-13 NMR signals and resulted in a unique P-31 signal for each compound. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00178-7
• 作为产物：
  描述：

  2-[(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 在 4-二甲氨基吡啶 、 四丁基碘化铵 、 乙二胺 、 三乙胺 、 palladium dichloride 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 59.0h， 生成 octyl 2,4,6-tri-O-benzyl-3-O-diphenoxyphosphono-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and NMR characterization of the six regioisomeric monophosphates of octyl β-d-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-d-glucopyranoside

  摘要：

  All six regioisomeric monophosphates of octyl beta-D-galactopyranosyl-(1 --> 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside have been chemically synthesized and characterized by high-resolution H-1, C-13 and P-31 NMR spectroscopy. Phosphorylation causes characteristic downfield shifts of the nucleus at the substituted site in the H-1 and C-13 NMR signals and resulted in a unique P-31 signal for each compound. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00178-7