3-O-acetyl-2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-α-D-mannopyranose | 1344088-81-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-O-acetyl-2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-α-D-mannopyranose
• CAS: 1344088-81-8
• 化学式: C₂₇H₄₄O₉Si₂
• 分子量: 568.812
• InChiKey: LWHOOUZWWPLLHQ-RYIFMDQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  109.75
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  3-O-acetyl-2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-α-D-mannopyranose 在 三氟甲磺酸三甲基硅酯 、 potassium carbonate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 17.5h， 生成 octyl 3-O-acetyl-2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-α-D-mannopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of octyl S-glycosides of tri- to pentasaccharide fragments related to the GPI anchor of Trypanosoma brucei

  摘要：

  The three oligosaccharide octyl-S-glycosides Man-alpha 1,6-Man-alpha 1,4-GlcNH(2)-alpha 1,S-Octyl (19), Man-alpha 1,6-(Gal-alpha 1,3)Man-alpha 1,4-GlcNH(2)-alpha 1,S-Octyl (27) and Man-alpha 1,2-Man-alpha 1,6-(Gal-alpha 1,3)Man-alpha 1,4-GlcNH(2)-alpha 1,S-Octyl (37), related to the GPI anchor of Trypanosoma brucei were prepared by a stepwise and block-wise approach from octyl 2-azido-2-deoxy-3,6-di-O-benzyl-1-thio-alpha-D-glucopyranoside (8) and octyl 2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-1-thio-alpha-D-mannopyransoside (9). Glucosamine derivative 8 was obtained from 1,3,4,6-tetra-O-acetyl-2-azido-2-desoxy-beta-D-glucopyranose (1) in five steps. Mannoside 9 was converted into the corresponding imidate 12 and coupled with 8 to give disaccharide octyl-S-glycoside 13 which was further mannosylated to afford trisaccharide 19 upon deprotection. Likewise, mannoside 9 was galactosylated, converted into the corresponding imidate and coupled with 8 to give trisaccharide 25. Mannosylation of the latter afforded tetrasaccharide 27 upon deprotection. Condensation of 25 with disaccharide imidate 35 gave, upon deprotection of the intermediates, the corresponding pentasaccharide octyl-S-glycoside 37. Saccharides 19, 27 and 37 are suitable substrates for studying the enzymatic glycosylation pattern of the GPI anchor of T. brucei. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.08.001
• 作为产物：
  描述：

  octyl 3-O-acetyl-2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-1-thio-α-D-mannopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 丙酮 为溶剂， 反应 0.17h， 以76%的产率得到3-O-acetyl-2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-α-D-mannopyranose
  参考文献：
  名称：

  Synthesis of octyl S-glycosides of tri- to pentasaccharide fragments related to the GPI anchor of Trypanosoma brucei

  摘要：

  The three oligosaccharide octyl-S-glycosides Man-alpha 1,6-Man-alpha 1,4-GlcNH(2)-alpha 1,S-Octyl (19), Man-alpha 1,6-(Gal-alpha 1,3)Man-alpha 1,4-GlcNH(2)-alpha 1,S-Octyl (27) and Man-alpha 1,2-Man-alpha 1,6-(Gal-alpha 1,3)Man-alpha 1,4-GlcNH(2)-alpha 1,S-Octyl (37), related to the GPI anchor of Trypanosoma brucei were prepared by a stepwise and block-wise approach from octyl 2-azido-2-deoxy-3,6-di-O-benzyl-1-thio-alpha-D-glucopyranoside (8) and octyl 2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-1-thio-alpha-D-mannopyransoside (9). Glucosamine derivative 8 was obtained from 1,3,4,6-tetra-O-acetyl-2-azido-2-desoxy-beta-D-glucopyranose (1) in five steps. Mannoside 9 was converted into the corresponding imidate 12 and coupled with 8 to give disaccharide octyl-S-glycoside 13 which was further mannosylated to afford trisaccharide 19 upon deprotection. Likewise, mannoside 9 was galactosylated, converted into the corresponding imidate and coupled with 8 to give trisaccharide 25. Mannosylation of the latter afforded tetrasaccharide 27 upon deprotection. Condensation of 25 with disaccharide imidate 35 gave, upon deprotection of the intermediates, the corresponding pentasaccharide octyl-S-glycoside 37. Saccharides 19, 27 and 37 are suitable substrates for studying the enzymatic glycosylation pattern of the GPI anchor of T. brucei. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.08.001