2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,4-di-O-acetyl-3-O-allyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride | 905714-90-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,4-di-O-acetyl-3-O-allyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride
• CAS: 905714-90-1
• 化学式: C₇₀H₇₄FNO₁₉
• 分子量: 1252.35
• InChiKey: UUWZXVCAPYJOBK-HPZUWEHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.75
• 重原子数：
  91.0
• 可旋转键数：
  29.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  217.81
• 氢给体数：
  0.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,4-di-O-acetyl-3-O-allyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride 、 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide 在 4 Angstroem MS 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.08h， 以70%的产率得到2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,4-di-O-acetyl-3-O-allyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide
  参考文献：
  名称：

  Synthesis of the sugar moiety of TIME-EA4, a glycopeptide isolated from silkworm diapause eggs

  摘要：

  We describe the efficient synthesis of the tetrasaccharide, 2-O-acetyl-3,4,6-tri-O-benzyl-alpha-D-mannopyranosyl-(1 -> 6)-2,4-di-O-acetyl-3-O-allyl-p-D-mannopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-O-D-glucopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl azide, which is the protected form of the sugar unit of TIME-EA4 that is isolated from the diapausing eggs of the silkworm, Bombyx mori. The P-linked D-mannoside of the tetrasaccharide was obtained using the conventional oxidation-reduction method for inversion of the configuration at the C-2 hydroxyl group Of P-D-glucoside. The reduction was effected with NaBH4 in a methanolic solution in a ratio of 98:2 in favor of the P-D-mannoside that was obtained in 87% yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.015
• 作为产物：
  描述：

  p-methoxyphenyl 3-O-allyl-4,6-O-benzylidene-β-D-arabino-hex-2-ulopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 吡啶 、 sodium tetrahydroborate 、 二甲氨基三氟化硫 、 4 Angstroem MS 、 氢氟酸 、 对甲苯磺酸 、 乙二醇 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.27h， 生成 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,4-di-O-acetyl-3-O-allyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl fluoride
  参考文献：
  名称：

  Synthesis of the sugar moiety of TIME-EA4, a glycopeptide isolated from silkworm diapause eggs

  摘要：

  We describe the efficient synthesis of the tetrasaccharide, 2-O-acetyl-3,4,6-tri-O-benzyl-alpha-D-mannopyranosyl-(1 -> 6)-2,4-di-O-acetyl-3-O-allyl-p-D-mannopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-O-D-glucopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl azide, which is the protected form of the sugar unit of TIME-EA4 that is isolated from the diapausing eggs of the silkworm, Bombyx mori. The P-linked D-mannoside of the tetrasaccharide was obtained using the conventional oxidation-reduction method for inversion of the configuration at the C-2 hydroxyl group Of P-D-glucoside. The reduction was effected with NaBH4 in a methanolic solution in a ratio of 98:2 in favor of the P-D-mannoside that was obtained in 87% yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.04.015