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 | 1203582-49-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: 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
• CAS: 1203582-49-3
• 化学式: C₅₄H₆₂N₄O₁₁Si
• 分子量: 971.192
• InChiKey: JCWSGBZSHGPNIT-XSXKVGCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.15
• 重原子数：
  70.0
• 可旋转键数：
  20.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  180.21
• 氢给体数：
  1.0
• 氢受体数：
  12.0

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 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以78%的产率得到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：

  A novel polycondensation method for the synthesis of a two-faced β-1,4-glucan

  摘要：

  The stereospecific synthesis of a chitosan derivative repeating 2-azido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-D-glucopyranose, which has two distinguishing faces, was achieved by polycondensation of the sole starting disaccharide, trichloroacetimidoyl 2-azido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-D-glucopyranoside in a short and efficient way.

  DOI：

  10.1007/s00706-009-0173-z
• 作为产物：
  描述：

  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-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以97%的产率得到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
  参考文献：
  名称：

  A novel polycondensation method for the synthesis of a two-faced β-1,4-glucan

  摘要：

  The stereospecific synthesis of a chitosan derivative repeating 2-azido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-D-glucopyranose, which has two distinguishing faces, was achieved by polycondensation of the sole starting disaccharide, trichloroacetimidoyl 2-azido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-D-glucopyranoside in a short and efficient way.

  DOI：

  10.1007/s00706-009-0173-z

文献信息

• Synthesis of a chito-tetrasaccharide β-1,4-GlcNAc-β-1,4-GlcN repeating unit
  作者：Toshinari Kawada、Yuko Yoneda

  DOI：10.1007/s00706-009-0174-y

  日期：2009.10

  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.