benzyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside | 226211-27-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
• CAS: 226211-27-4
• 化学式: C₅₆H₅₁NO₁₅
• 分子量: 978.019
• InChiKey: DKOIYWGBDCDYEO-ARMYZXOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.19
• 重原子数：
  72.0
• 可旋转键数：
  17.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  189.68
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 以82%的产率得到benzyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->3)-2-acetamido-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of β-d-Galf-(1−3)-d-GlcNAc by the Trichloroacetamidate Method and of β-d-Galf-(1−6)-d-GlcNAc by SnCl₄-Promoted Glycosylation

  摘要：

  In a continuation of our studies on the characterization of the glycoproteins of T. cruzi new galactofuranosyl disaccharides were synthesized. beta-D-Galf-(1-3)-D-GlcNAc (1) was prepared by employing the trichloroacetamidate procedure for the glycosylation step, The mild conditions of this reaction are appropriate for condensation of 2,3,5,6-tetra-O-benzoyl-beta-D-galactofuranosyl trichloroacetamidate (6) with acid-labile benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-alpha-D-glucopyranoside (3). On the other hand, tin(IV) chloride promoted condensation of benzyl 2-acetamido-3-O-benzoyl-2-deoxy-alpha-D-glucopyranoside (11) with penta-O-benzoyl-alpha,beta-D-galactofuranose (4) gave the derivative of beta-D-Galf-(1-6)-D-GlcNAc (2) in 78% yield.

  DOI：

  10.1021/ol9905811
• 作为产物：
  描述：

  [(2R)-2-benzoyloxy-2-[(2S,3S,4R)-3,4-dibenzoyloxy-5-bromooxolan-2-yl]ethyl] benzoate 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 silver carbonate 作用下， 以 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 2.17h， 生成 benzyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of β-d-Galf-(1−3)-d-GlcNAc by the Trichloroacetamidate Method and of β-d-Galf-(1−6)-d-GlcNAc by SnCl₄-Promoted Glycosylation

  摘要：

  In a continuation of our studies on the characterization of the glycoproteins of T. cruzi new galactofuranosyl disaccharides were synthesized. beta-D-Galf-(1-3)-D-GlcNAc (1) was prepared by employing the trichloroacetamidate procedure for the glycosylation step, The mild conditions of this reaction are appropriate for condensation of 2,3,5,6-tetra-O-benzoyl-beta-D-galactofuranosyl trichloroacetamidate (6) with acid-labile benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-alpha-D-glucopyranoside (3). On the other hand, tin(IV) chloride promoted condensation of benzyl 2-acetamido-3-O-benzoyl-2-deoxy-alpha-D-glucopyranoside (11) with penta-O-benzoyl-alpha,beta-D-galactofuranose (4) gave the derivative of beta-D-Galf-(1-6)-D-GlcNAc (2) in 78% yield.

  DOI：

  10.1021/ol9905811