trichloroacetimidoyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-deoxy-3,6-di-O-benzyl-2-phthalimido-D-glucopyranoside | 1203584-81-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trichloroacetimidoyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-deoxy-3,6-di-O-benzyl-2-phthalimido-D-glucopyranoside
• CAS: 1203584-81-9
• 化学式: C₅₂H₅₀Cl₃N₅O₁₂
• 分子量: 1043.35
• InChiKey: ZEYGKRINZNPUAC-FPOPFPTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.07
• 重原子数：
  72.0
• 可旋转键数：
  20.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  210.13
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  tert-butyldimethylsilyl (2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-deoxy-3,6-di-O-benzyl-2-phthalimido-β-D-glucopyranoside 、 trichloroacetimidoyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-deoxy-3,6-di-O-benzyl-2-phthalimido-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到tert-butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-deoxy-3,6-di-O-benzyl-2-phthalimido-β-D-glucopyranosyl)-(1→4)-(2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-deoxy-3,6-di-O-benzyl-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a chito-tetrasaccharide β-1,4-GlcNAc-β-1,4-GlcN repeating unit

  摘要：

  tert-Butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranosyl)-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside (Kawada and Yoneda [MOCHEM-D-09-00120], 2009), designed as a repeating disaccharide unit in a beta-glucan having two different faces, was converted into a glycosyl donor and an acceptor. The glycosyl acceptor was glycosylated with the donor to afford a chito-tetrasaccharide derivative in good yield. Phthalimido and azido groups in the tetrasaccharide were successively converted into acetamido and free amino groups, and all other protecting groups were cleaved to obtain the chito-tetrasaccharide (2-amino-2-deoxy-beta-D-glucopyranosyl)-(1 -> 4)-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1 -> 4)-(2-amino-2-deoxy-beta-D-glucopyranosyl)-(1 -> 4)-2-acetamido-2-deoxy-D-glucopyranose.

  DOI：

  10.1007/s00706-009-0174-y
• 作为产物：
  描述：

  (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-deoxy-3,6-di-O-benzyl-2-phthalimido-D-glucopyranose 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到trichloroacetimidoyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-deoxy-3,6-di-O-benzyl-2-phthalimido-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a chito-tetrasaccharide β-1,4-GlcNAc-β-1,4-GlcN repeating unit

  摘要：

  tert-Butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranosyl)-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside (Kawada and Yoneda [MOCHEM-D-09-00120], 2009), designed as a repeating disaccharide unit in a beta-glucan having two different faces, was converted into a glycosyl donor and an acceptor. The glycosyl acceptor was glycosylated with the donor to afford a chito-tetrasaccharide derivative in good yield. Phthalimido and azido groups in the tetrasaccharide were successively converted into acetamido and free amino groups, and all other protecting groups were cleaved to obtain the chito-tetrasaccharide (2-amino-2-deoxy-beta-D-glucopyranosyl)-(1 -> 4)-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1 -> 4)-(2-amino-2-deoxy-beta-D-glucopyranosyl)-(1 -> 4)-2-acetamido-2-deoxy-D-glucopyranose.

  DOI：

  10.1007/s00706-009-0174-y