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-glucopyranose | 905714-89-8

• 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-glucopyranose
• CAS: 905714-89-8
• 化学式: C₇₀H₇₅NO₂₀
• 分子量: 1250.36
• InChiKey: UFZACRAEJGITBB-ADGKDBQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.78
• 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：
  238.04
• 氢给体数：
  1.0
• 氢受体数：
  20.0

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-glucopyranose 在 二甲氨基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以77%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 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
• 作为产物：
  描述：

  p-methoxyphenyl 3-O-allyl-6-O-tert-butyldimethylsilyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 吡啶 、 4 Angstroem MS 、 氢氟酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.08h， 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-glucopyranose
  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