3,4,6-tri-O-acetyl-1-O-(N-allyl)carbamoyl-2-deoxy-2-phthalimido-β-D-glucopyranose | 150630-95-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-acetyl-1-O-(N-allyl)carbamoyl-2-deoxy-2-phthalimido-β-D-glucopyranose
• CAS: 150630-95-8
• 化学式: C₂₄H₂₆N₂O₁₁
• 分子量: 518.477
• InChiKey: FVXKFFDFKGOXBL-ZFVCPDAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  163.84
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-1-O-(N-allyl)carbamoyl-2-deoxy-2-phthalimido-β-D-glucopyranose 在 ethandithiol 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 9.5h， 生成 3-O-(2',3',4'-tri-O-acetyl-6'-O-benzyl-β-D-galactopyranosyl)-6-O-(3'',4''.6''-tri-O-acetyl-2''-deoxy-2''-phthalimido-β-D-glucopyranosyl)-2-azido-2-deoxy-1-O-thexyldimethylsilyl-β-D-galactopyranose
  参考文献：
  名称：

  Oligosaccharide Synthesis via Electrophile-Induced Activation of Glycosyl-N-Allylcarbamates

  摘要：

  Glycosyl-N-allyl carbamates, obtained by reaction of anomerically unprotected saccharides with allyl isocyanate, can be activated by an electrophile-induced cyclisation and reacted with glycosyl accepters to form the corresponding oligosaccharides. By this method the mucin core 2 trisaccharide(2) has successfully been synthesized. Due to the mild glycosylation conditions even 1-O-acetyl protected glycosyl accepters can be used. This was demonstrated in the synthesis of a 1,6-linked glucosyl trisaccharide whereby a reptitious glycosylation strategy could be applied.

  DOI：

  10.1080/07328309808002350
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 在 乙酸肼 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 3,4,6-tri-O-acetyl-1-O-(N-allyl)carbamoyl-2-deoxy-2-phthalimido-β-D-glucopyranose
  参考文献：
  名称：

  Oligosaccharide Synthesis via Electrophile-Induced Activation of Glycosyl-N-Allylcarbamates

  摘要：

  Glycosyl-N-allyl carbamates, obtained by reaction of anomerically unprotected saccharides with allyl isocyanate, can be activated by an electrophile-induced cyclisation and reacted with glycosyl accepters to form the corresponding oligosaccharides. By this method the mucin core 2 trisaccharide(2) has successfully been synthesized. Due to the mild glycosylation conditions even 1-O-acetyl protected glycosyl accepters can be used. This was demonstrated in the synthesis of a 1,6-linked glucosyl trisaccharide whereby a reptitious glycosylation strategy could be applied.

  DOI：

  10.1080/07328309808002350

文献信息

• Glycoside synthesis via electrophile-induced activation of N-allyl carbamates
  作者：Horst Kunz、Jörg Zimmer

  DOI：10.1016/s0040-4039(00)60478-1

  日期：1993.4

  O-Benzyl-, O-acyl-, N-acyl- and isopropylidene-protected glycosyl N-allylcarbamates, obtained from anomerically unprotected monosaccharides and allyl isocyanate, are activated by an electrophile-induced cyclisation and react with hydroxyl compounds to form the corresponding glycosides.

  由未保护的单糖和异氰酸烯丙酯得到的O-苄基，O-酰基，N-酰基和异亚丙基保护的糖基N-烯丙基氨基甲酸酯，通过亲电试剂诱导的环化反应活化，并与羟基化合物反应形成相应的糖苷。