4-methylphenyl 6-O-acetyl-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranoside | 1374561-82-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methylphenyl 6-O-acetyl-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranoside
• CAS: 1374561-82-6
• 化学式: C₆₉H₇₀BrN₃O₁₁SSi
• 分子量: 1257.38
• InChiKey: LTNRHOWVVPPZDE-AGZBIORZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.64
• 重原子数：
  86.0
• 可旋转键数：
  23.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  165.97
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  4-methylphenyl 6-O-acetyl-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranoside 、 Methyl 2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以86%的产率得到methyl 4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-(1->4)-[6-O-acetyl-2-O-benzoyl-3-O-benzyl-β-D-glucopyranosyl]-(1->4)-2-azido-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  α-Glycosylation by d-Glucosamine-Derived Donors: Synthesis of Heparosan and Heparin Analogues That Interact with Mycobacterial Heparin-Binding Hemagglutinin

  摘要：

  Numerous biomolecules possess alpha-D-glucosamine as structural component. However, chemical glycosylations aimed at this backbone are usually not easily attained without generating the unwanted beta-isomer. We report herein a versatile approach in affording full alpha-stereoselectivity built upon a carefully selected set of orthogonal protecting groups on a D-glucosaminyl donor. The excellent stereoselectivity provided by the protecting group combination was found independent of leaving groups and activators. With the trichloroacetimidate as the optimum donor leaving group, core skeletons of glycosylphosphatidyl inositol anchors, heparosan, heparan sulfate, and heparin were efficiently assembled. The orthogonal protecting groups were successfully manipulated to further carry out the total syntheses of heparosan tri- and pentasaccharides and heparin di-, tetra-, hexa-, and octasaccharide analogues. Using the heparin analogues, heparin-binding hemagglutinin, a virulence factor of Mycobacterium tuberculosis, was found to bind at least six sugar units with the interaction notably being entropically driven.

  DOI：

  10.1021/ja302640p
• 作为产物：
  描述：

  4-methylphenyl 6-O-acetyl-2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranoside 、 2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-D-glucopyranosyl trichloroacetimidate 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以70%的产率得到4-methylphenyl 6-O-acetyl-4-O-[2-azido-3-O-(4-bromobenzyl)-6-O-tert-butyldiphenylsilyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  肝素类抗凝药Fondaparinux的合成

  摘要：

  Fondaparinux是一种基于肝素抗凝血酶结合结构域的合成五糖，是公认的临床抗凝剂。尽管在许多情况下它是替代药物肝素的更好，更安全的替代方法，但由于合成困难而乏味，其高昂的成本阻碍了其广泛使用。磺达肝素的化学合成以有效和简洁的方式从可商购获得d -葡糖胺，二丙酮α- d葡萄糖和五-O-乙酰基d -葡萄糖。该方法涉及适当功能化的构建基块，这些构建基块易于使用，并使用共享的中间体和一系列单反应，从而显着减少了合成工作量并提高了收率。

  DOI：

  10.1002/anie.201404154