p-methoxyphenyl (2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-(6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside | 1192219-54-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl (2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-(6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)]Man(b1-4)[Bn(-2)][Bn(-3)][Bz(-6)]Man(b1-3)[Bz(-2)][Bz(-4)][Bz(-6)]Gal(b)-O-Ph(4-OMe)；[(2R,3R,4S,5S,6S)-6-[(2R,3S,4S,5R,6S)-3,5-dibenzoyloxy-2-(benzoyloxymethyl)-6-(4-methoxyphenoxy)oxan-4-yl]oxy-3-[(2S,3S,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-4,5-bis(phenylmethoxy)oxan-2-yl]methyl benzoate
• CAS: 1192219-54-7
• 化学式: C₈₈H₈₄O₂₁
• 分子量: 1477.62
• InChiKey: PXZFOIQJKYEQAI-KZHSSBCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14
• 重原子数：
  109
• 可旋转键数：
  37
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  236
• 氢给体数：
  1
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  (2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-(6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzoyl-D-galactopyranose 、 p-methoxyphenyl (2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-(6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside 在 苯酐 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以69%的产率得到p-methoxyphenyl (2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-(6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranosyl)-(1->3)-(2,4,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->6)-(2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-(6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of the Hexasaccharide Repeating Unit of the Cell Wall Polysaccharide fromKineosporia aurantiacaVKM Ac-720^TEmploying the Direct Glycosylation with Anomeric Hydroxy Sugars Involving Glycosyl Phthalate Intermediates

  摘要：

  Synthesis of a suitably protected form of the hexasaccharide repeating unit of the cell wall polymer from Kineosporia aurantiaca VKM Ac-720(T) has been achieved by the stereoselective direct glycosylation of a trisaccharide acceptor with a trisaccharide donor having an anomeric hydroxy group involving a glycosyl phthalate intermediate. Both the trisaccharide acceptor and the trisaccharide donor were obtained from a common trisaccharide, of which two beta-mannopyranosyl linkages were constructed stereoselectively by employing the direct glycosylation method with the anomeric hydroxy sugar involving a glycosyl phthalate intermediate and the 2'-carboxybenzyl glycoside method, respectively.

  DOI：

  10.1080/07328300903003352
• 作为产物：
  描述：

  p-methoxyphenyl (2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-(6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside 在 硼烷四氢呋喃络合物 、 三氟甲磺酸二丁硼 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到p-methoxyphenyl (2,3,4-tri-O-benzyl-β-D-mannopyranosyl)-(1->4)-(6-O-benzoyl-2,3-di-O-benzyl-β-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of the Hexasaccharide Repeating Unit of the Cell Wall Polysaccharide fromKineosporia aurantiacaVKM Ac-720^TEmploying the Direct Glycosylation with Anomeric Hydroxy Sugars Involving Glycosyl Phthalate Intermediates

  摘要：

  Synthesis of a suitably protected form of the hexasaccharide repeating unit of the cell wall polymer from Kineosporia aurantiaca VKM Ac-720(T) has been achieved by the stereoselective direct glycosylation of a trisaccharide acceptor with a trisaccharide donor having an anomeric hydroxy group involving a glycosyl phthalate intermediate. Both the trisaccharide acceptor and the trisaccharide donor were obtained from a common trisaccharide, of which two beta-mannopyranosyl linkages were constructed stereoselectively by employing the direct glycosylation method with the anomeric hydroxy sugar involving a glycosyl phthalate intermediate and the 2'-carboxybenzyl glycoside method, respectively.

  DOI：

  10.1080/07328300903003352

文献信息

• Stereoselective Synthesis of the Hexasaccharide Repeating Unit of the Cell Wall Polysaccharide from<i>Kineosporia aurantiaca</i>VKM Ac-720^TEmploying the Direct Glycosylation with Anomeric Hydroxy Sugars Involving Glycosyl Phthalate Intermediates
  作者：So Mi Park、Dae-Hwan Suk、Kwan Soo Kim

  DOI：10.1080/07328300903003352

  日期：2009.7.29

  Synthesis of a suitably protected form of the hexasaccharide repeating unit of the cell wall polymer from Kineosporia aurantiaca VKM Ac-720(T) has been achieved by the stereoselective direct glycosylation of a trisaccharide acceptor with a trisaccharide donor having an anomeric hydroxy group involving a glycosyl phthalate intermediate. Both the trisaccharide acceptor and the trisaccharide donor were obtained from a common trisaccharide, of which two beta-mannopyranosyl linkages were constructed stereoselectively by employing the direct glycosylation method with the anomeric hydroxy sugar involving a glycosyl phthalate intermediate and the 2'-carboxybenzyl glycoside method, respectively.