octyl α-D-mannopyranosyl-(1->6)-α-D-mannopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside | 1344088-87-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: octyl α-D-mannopyranosyl-(1->6)-α-D-mannopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside
• 英文别名: (2S,3S,4S,5S,6R)-2-[[(2R,3S,4S,5S,6R)-6-[(2R,3S,4R,5R,6R)-5-azido-6-octylsulfanyl-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1344088-87-4
• 化学式: C₄₀H₅₉N₃O₁₄S
• 分子量: 837.986
• InChiKey: YJJWQSWFWJARRS-RMWOJILLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  58
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  246
• 氢给体数：
  7
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  octyl α-D-mannopyranosyl-(1->6)-α-D-mannopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 0.42h， 以51%的产率得到octyl α-D-mannopyranosyl-(1->6)-α-D-mannopyranosyl-(1->4)-2-amino-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 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1->6)-3-O-acetyl-2-O-benzoyl-α-D-mannopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以93%的产率得到octyl α-D-mannopyranosyl-(1->6)-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

文献信息

• Synthesis of octyl S-glycosides of tri- to pentasaccharide fragments related to the GPI anchor of Trypanosoma brucei
  作者：Ralf Dettmann、Thomas Ziegler

  DOI：10.1016/j.carres.2011.08.001

  日期：2011.11

  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.