(2S,3S,4R,5S,6R)-4,5-Bis-benzyloxy-6-((S)-1,2-bis-benzyloxy-ethyl)-2-methoxy-tetrahydro-pyran-3-ol | 211231-15-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S,4R,5S,6R)-4,5-Bis-benzyloxy-6-((S)-1,2-bis-benzyloxy-ethyl)-2-methoxy-tetrahydro-pyran-3-ol
• CAS: 211231-15-1
• 化学式: C₃₆H₄₀O₇
• 分子量: 584.709
• InChiKey: ZMZUNVMJMIAGGI-KDWQFJMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.69
• 重原子数：
  43.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.61
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5S,6R)-4,5-Bis-benzyloxy-6-((S)-1,2-bis-benzyloxy-ethyl)-2-methoxy-tetrahydro-pyran-3-ol 在 四氮唑 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 3-[(2S,3S,4S,5S,6R)-4,5-Bis-benzyloxy-6-((S)-1,2-bis-benzyloxy-ethyl)-2-methoxy-tetrahydro-pyran-3-yloxy]-1,5-dihydro-benzo[e][1,3,2]dioxaphosphepine 3-oxide
  参考文献：
  名称：

  Five monophosphates of methyl l-glycero-α-d-manno-heptopyranoside: synthesis, hydrolysis and migrations

  摘要：

  From suitably protected methyl alpha-D-mannopyranosides five methyl L-glycero-alpha-D-manno-heptopyranosides were synthesized by the one-carbon-atom chain elongation at C-6 and converted to five monophosphates (1-5) having the PO(OH)(2) group at O-2, -3, -4, -6 and -7. Compounds 1-5 were exposed to acidic and basic hydrolytic conditions used in lipopolysaccharide analysis and the products and their proportion were determined. Under acidic conditions, besides hydrolysis of the glycoside, migrations and hydrolytic cleavage of the phosphate residue were found. Under basic conditions the phosphates were stable. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00037-8
• 作为产物：
  描述：

  (2S,3S,4S,5S,6S)-5-Allyloxy-3,4-bis-benzyloxy-6-methoxy-tetrahydro-pyran-2-carbaldehyde 在 Wilkinson's catalyst bicyclo[2.2.2]octane-1,4-diamine 、 sodium hydride 、 magnesium 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 25.0h， 生成 (2S,3S,4R,5S,6R)-4,5-Bis-benzyloxy-6-((S)-1,2-bis-benzyloxy-ethyl)-2-methoxy-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  Five monophosphates of methyl l-glycero-α-d-manno-heptopyranoside: synthesis, hydrolysis and migrations

  摘要：

  From suitably protected methyl alpha-D-mannopyranosides five methyl L-glycero-alpha-D-manno-heptopyranosides were synthesized by the one-carbon-atom chain elongation at C-6 and converted to five monophosphates (1-5) having the PO(OH)(2) group at O-2, -3, -4, -6 and -7. Compounds 1-5 were exposed to acidic and basic hydrolytic conditions used in lipopolysaccharide analysis and the products and their proportion were determined. Under acidic conditions, besides hydrolysis of the glycoside, migrations and hydrolytic cleavage of the phosphate residue were found. Under basic conditions the phosphates were stable. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00037-8