methyl 2,3,4-tri-O-benzyl-6-O-[3,4,6-tri-O-benzyl-2-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-α-D-mannopyranoside | 313467-42-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6-O-[3,4,6-tri-O-benzyl-2-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-α-D-mannopyranoside
• 英文别名: Bn(-3)[Bn(-4)][Bn(-6)]Man(a1-2)[Bn(-3)][Bn(-4)][Bn(-6)]Man(a1-6)[Bn(-2)][Bn(-3)][Bn(-4)]a-Man1Me；(2R,3S,4R,5R,6R)-2-[(2S,3S,4S,5R,6R)-2-[[(2R,3R,4S,5S,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 313467-42-4
• 化学式: C₈₂H₈₈O₁₆
• 分子量: 1329.59
• InChiKey: MFQWXOLBYGPLBG-YZMDYHJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  98
• 可旋转键数：
  35
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  159
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-lactosyl trichloroacetimidate 、 methyl 2,3,4-tri-O-benzyl-6-O-[3,4,6-tri-O-benzyl-2-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-α-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 Angstroem MS 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以45%的产率得到methyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->2)-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of galactosyl and lactosyl derivatives as potential anti-metastasis compounds

  摘要：

  Based on the known anti-metastasis activities of lactosides and galactosides, a galactosyl and a lactosyl trimannoside were prepared via the conventional Koenigs-Knorr and trichloroacetimidate methods, respectively. Through typical deblocking procedures, a tetrasaccharide alpha-D-Galp-(1-->2)-alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->6)-alpha-D-ManpOCH(3) and a pentasaccharide beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->2)-alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->6)-alpha-D-ManpOCH(3) were obtained. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00137-3
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-O-[3,4,6-tri-O-benzyl-2-O(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-α-D-mannopyranoside 在 sodium 作用下， 以 甲醇 为溶剂， 以83.7%的产率得到methyl 2,3,4-tri-O-benzyl-6-O-[3,4,6-tri-O-benzyl-2-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranosyl]-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of galactosyl and lactosyl derivatives as potential anti-metastasis compounds

  摘要：

  Based on the known anti-metastasis activities of lactosides and galactosides, a galactosyl and a lactosyl trimannoside were prepared via the conventional Koenigs-Knorr and trichloroacetimidate methods, respectively. Through typical deblocking procedures, a tetrasaccharide alpha-D-Galp-(1-->2)-alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->6)-alpha-D-ManpOCH(3) and a pentasaccharide beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->2)-alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->6)-alpha-D-ManpOCH(3) were obtained. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00137-3

文献信息

• Synthesis of galactosyl and lactosyl derivatives as potential anti-metastasis compounds
  作者：Hui Li、Qing Li、Meng-Shen Cai、Zhong-Jun Li

  DOI：10.1016/s0008-6215(00)00137-3

  日期：2000.10

  Based on the known anti-metastasis activities of lactosides and galactosides, a galactosyl and a lactosyl trimannoside were prepared via the conventional Koenigs-Knorr and trichloroacetimidate methods, respectively. Through typical deblocking procedures, a tetrasaccharide alpha-D-Galp-(1-->2)-alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->6)-alpha-D-ManpOCH(3) and a pentasaccharide beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->2)-alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->6)-alpha-D-ManpOCH(3) were obtained. (C) 2000 Elsevier Science Ltd. All rights reserved.