tert-butyldimethylsilyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside | 1203588-91-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: tert-butyldimethylsilyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS: 1203588-91-3
• 化学式: C₃₄H₃₉NO₇Si
• 分子量: 601.772
• InChiKey: RJUVOLDAOHMBTO-ZGEIMPGHSA-N

物化性质

• 沸点：
  662.8±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  43.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  83.53
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  tert-butyldimethylsilyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 吡啶 、 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 、 乙二胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 正丁醇 为溶剂， 反应 1.0h， 生成 tert-butyldimethylsilyl 2-acetamido-4-O-(4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Selection of protecting groups and synthesis of a β-1,4-GlcNAc-β-1,4-GlcN unit

  摘要：

  The synthesis of the disaccharide tert-butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside, designed as a repeating unit appearing in oligo-and polysaccharides, which exhibits a distinguished "obverse-reverse" property in beta-1,4-glucan chain, was accomplished. This disaccharide was synthesized by glycosylation of a phthalimido sugar with an azido sugar. A selective removal of the two different protecting groups atC-2 for obtaining 2-acetamido-4-O-(2-amino-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-beta-D-glucopyranose indicates that the selection and combination, using phthalimido and azido as protecting groups, are an excellent strategy for synthesizing such target disaccharides.

  DOI：

  10.1007/s00706-009-0172-0
• 作为产物：
  描述：

  苯甲醛二甲缩醛 在 四丁基碘化铵 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 mineral oil 为溶剂， 30.0 ℃ 、4.0 kPa 条件下， 反应 13.5h， 生成 tert-butyldimethylsilyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Selection of protecting groups and synthesis of a β-1,4-GlcNAc-β-1,4-GlcN unit

  摘要：

  The synthesis of the disaccharide tert-butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside, designed as a repeating unit appearing in oligo-and polysaccharides, which exhibits a distinguished "obverse-reverse" property in beta-1,4-glucan chain, was accomplished. This disaccharide was synthesized by glycosylation of a phthalimido sugar with an azido sugar. A selective removal of the two different protecting groups atC-2 for obtaining 2-acetamido-4-O-(2-amino-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-beta-D-glucopyranose indicates that the selection and combination, using phthalimido and azido as protecting groups, are an excellent strategy for synthesizing such target disaccharides.

  DOI：

  10.1007/s00706-009-0172-0