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 | 1203582-46-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: 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；tert-butyldimethylsilyl 4-O-(4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside；[(2R,3S,4R,5R,6S)-5-azido-6-[(2R,3S,4R,5R,6S)-6-[tert-butyl(dimethyl)silyl]oxy-5-(1,3-dioxoisoindol-2-yl)-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 1203582-46-0
• 化学式: C₅₆H₆₄N₄O₁₂Si
• 分子量: 1013.23
• InChiKey: DBIMRJIGWSUUEW-HWWNQMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.72
• 重原子数：
  73.0
• 可旋转键数：
  21.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  186.28
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  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 吡啶 、 甲醇 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 、 sodium methylate 、 溶剂黄146 、 乙二胺 作用下， 以 四氢呋喃 、 乙醇 、 水 、 正丁醇 为溶剂， 90.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 生成 2-amino-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranose
  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：

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

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.
• A novel polycondensation method for the synthesis of a two-faced β-1,4-glucan
  作者：Toshinari Kawada、Yuko Yoneda、Kensaku Shimizu、Chiori Itoh

  DOI：10.1007/s00706-009-0173-z

  日期：2009.10

  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.