tert-butyldimethylsilyl (2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside | 1203584-84-2

• 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-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS: 1203584-84-2
• 化学式: C₉₀H₁₀₈N₈O₁₉Si
• 分子量: 1633.98
• InChiKey: IAEKPQRSSOIMAH-SGBYNWQTSA-N

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-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-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， 以93%的产率得到(2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-D-glucopyranose
  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：

  tert-butyldimethylsilyl (4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-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-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-(2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-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