allyl [methyl(2,4-di-O-benzoyl-β-D-glucopyranosyl)uronate] | 404350-50-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl [methyl(2,4-di-O-benzoyl-β-D-glucopyranosyl)uronate]
• 英文别名: methyl (2S,3S,4S,5R,6R)-3,5-dibenzoyloxy-4-hydroxy-6-prop-2-enoxyoxane-2-carboxylate
• CAS: 404350-50-1
• 化学式: C₂₄H₂₄O₉
• 分子量: 456.449
• InChiKey: YNXCOQXYTAROCE-BPJSAFFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  allyl [methyl(2,4-di-O-benzoyl-β-D-glucopyranosyl)uronate] 在 吡啶 、 potassium carbonate 、 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 28.5h， 生成 methyl (3-O-acetyl-2,4-di-O-benzoyl-α-D-glucopyranosyl trichloroacetamidate)uronate
  参考文献：
  名称：

  Preparative route to glucuronyl donors bearing temporary protecting group at O-3 via 6,3-lactonisation by Bz2O or Piv2O

  摘要：

  Heating of non-substituted beta -D-glucopyranuronic acids in the presence of pivalic or benzoic anhydride in DMF gives 4-O-monoacylated or 2,4-di-O-acylated 6,3-lactones that can be easily transformed into corresponding methyl uronates bearing free OH-groups at C-2 and C-3 or C-3 only, respectively. This method was used for preparation of selectively 3-O-protected glucuronyl donors of thioglycoside and trichloracetimidate types. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00272-5
• 作为产物：
  描述：

  allyl (β-D-glucopyranosyluronic acid) 在 吡啶 、 4-二甲氨基吡啶 、 sodium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 allyl [methyl(2,4-di-O-benzoyl-β-D-glucopyranosyl)uronate]
  参考文献：
  名称：

  Preparative route to glucuronyl donors bearing temporary protecting group at O-3 via 6,3-lactonisation by Bz2O or Piv2O

  摘要：

  Heating of non-substituted beta -D-glucopyranuronic acids in the presence of pivalic or benzoic anhydride in DMF gives 4-O-monoacylated or 2,4-di-O-acylated 6,3-lactones that can be easily transformed into corresponding methyl uronates bearing free OH-groups at C-2 and C-3 or C-3 only, respectively. This method was used for preparation of selectively 3-O-protected glucuronyl donors of thioglycoside and trichloracetimidate types. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00272-5

文献信息

• Preparative route to glucuronyl donors bearing temporary protecting group at O-3 via 6,3-lactonisation by Bz2O or Piv2O
  作者：Andrei V Kornilov、Elena V Sukhova、Nikolay E Nifantiev

  DOI：10.1016/s0008-6215(01)00272-5

  日期：2001.12

  Heating of non-substituted beta -D-glucopyranuronic acids in the presence of pivalic or benzoic anhydride in DMF gives 4-O-monoacylated or 2,4-di-O-acylated 6,3-lactones that can be easily transformed into corresponding methyl uronates bearing free OH-groups at C-2 and C-3 or C-3 only, respectively. This method was used for preparation of selectively 3-O-protected glucuronyl donors of thioglycoside and trichloracetimidate types. (C) 2001 Elsevier Science Ltd. All rights reserved.