benzyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->6)-2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside | 206649-92-5

• 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->6)-2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside
• CAS: 206649-92-5
• 化学式: C₅₆H₅₁NO₁₆
• 分子量: 994.018
• InChiKey: HPJYKMZMRPTDJZ-PNLFXSNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.29
• 重原子数：
  73.0
• 可旋转键数：
  19.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  217.75
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  benzyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->6)-2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside 在 palladium on activated charcoal sodium methylate 、 ammonium formate 作用下， 以 甲醇 为溶剂， 反应 2.75h， 生成 β-D-galactofuranosyl-(1->6)-2-acetamido-2-deoxy-β-D-glucopyranose
  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：

  1,2,3,5,6-penta-O-benzoyl-D-galactofuranose 、 benzyl 2-acetamido-3-O-benzoyl-2-deoxy-α-D-glucopyranoside 在 四氯化锡 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 15.0h， 以78%的产率得到benzyl 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl-(1->6)-2-acetamido-3-O-benzoyl-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

文献信息

• One-pot synthesis of β-d-Gal>(1 → 4)[β-d-Galp(1 → 6)]-d-GlcNAc, a ‘core’ trisaccharide linked O-glycosidically in glycoproteins of Trypanosoma cruzi
  作者：Carola Gallo-Rodriguez、Oscar Varela、Rosa M. de Lederkremer

  DOI：10.1016/s0008-6215(97)00256-5

  日期：1997.12

  Tin(IV) chloride-promoted condensation of benzyl 2-acetamido-3-O-benzoyl-2-deoxy-alpha-D-glucopyranoside (4) with penta-O-benzoyl-beta-D-galactopyranose (6) gave the derivative of beta-D-Galp-(1 --> 6)-alpha-D-GlcNAc 7 in 80% yield, This was glycosylated with penta-O-benzoyl-alpha,beta- D-galactofuranose (5>, employing the same catalyst, to afford the protected benzyl per-O-benzoyl-beta-D-Galf(1 --> 4)[beta-D-Galp(1 --> 6)]D-GlcNAc 10 in 41% yield, Alternatively, compound 10 was obtained directly in a one-pot reaction from 4, by sequential addition of 6 and 5 (34% yield). beta-Glycosidic linkages were diastereoselectively formed. De-O-benzoylation of 10, followed by heterogeneous catalytic transfer hydrogenolysis of the benzyl group afforded the free trisaccharide beta-D-Galf(1 --> 4)[beta-D-Galp(1 --> 6)]-D-GlcNAc (14) in 98% yield from 10. Sodium borohydride reduction of 14 gave the corresponding alditol, whose spectral data were identical to those reported for the alditol obtained from the 38-43 kDa cell-surface glycoprotein of Trypanosoma cruzi. (C) 1998 Elsevier Science Ltd.