allyl 3,2,6-tri-O-benzyl-4-O-p-methoxybenzyl-D-glucopyranoside | 929619-12-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3,2,6-tri-O-benzyl-4-O-p-methoxybenzyl-D-glucopyranoside
• 英文别名: allyl 2,3,6-tri-O-benzyl-4-O-(4-methoxybenzyl)-D-glucopyranoside；Bn(-2)[Bn(-3)][Mob(-4)][Bn(-6)]Glc-O-allyl；(2R,3R,4S,5R)-3-[(4-methoxyphenyl)methoxy]-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-2-enoxyoxane
• CAS: 929619-12-5
• 化学式: C₃₈H₄₂O₇
• 分子量: 610.747
• InChiKey: KYDRJHZPPAXUFG-OXODQGHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  45
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  allyl 3,2,6-tri-O-benzyl-4-O-p-methoxybenzyl-D-glucopyranoside 在 三氟甲磺酸 、 4 A molecular sieve 、 potassium tert-butylate 、 乙酸酐 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 103.0h， 生成 3,4,5,7-tetra-O-benzyl-1-deoxy-α-D-gluco-hept-2-ulosyl-(2->4)-2,3,6-tri-O-benzyl-D-glucono-1,5-lactone
  参考文献：
  名称：

  Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols

  摘要：

  A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely a-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by (3)J(C,H) coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.032
• 作为产物：
  描述：

  D-葡萄糖 在 三氟化硼乙醚 、 sodium hydride 、 二异丁基氢化铝 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 129.0h， 生成 allyl 3,2,6-tri-O-benzyl-4-O-p-methoxybenzyl-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols

  摘要：

  A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely a-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by (3)J(C,H) coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.07.032

文献信息

• Development of Adamantan-1-yl-methoxy-Functionalized 1-Deoxynojirimycin Derivatives as Selective Inhibitors of Glucosylceramide Metabolism in Man
  作者：Tom Wennekes、Richard J. B. H. N. van den Berg、Wilma Donker、Gijsbert A. van der Marel、Anneke Strijland、Johannes M. F. G. Aerts、Herman S. Overkleeft

  DOI：10.1021/jo061280p

  日期：2007.2.1

  In this article, we present a straightforward synthesis of adamantan-1-yl-methoxy-functionalized 1-deoxynojirimycin derivatives. The used synthetic routes are flexible and can be used to create a wide variety of lipophilic mono- and difunctionalized 1-deoxynojirimycin derivatives. The compounds reported here are lipophilic iminosugar based on lead compound 4, a potent inhibitor of the three enzymes

  在本文中，我们介绍了金刚烷-1-基-甲氧基官能化的1-deoxynojirimycin衍生物的直接合成。所使用的合成路线是灵活的，并且可以用于产生多种亲脂性的单和双官能化的1-脱氧野oji霉素衍生物。此处报道的化合物是基于铅化合物4的亲脂性亚氨基糖，这是一种与糖鞘脂性葡萄糖基神经酰胺代谢有关的三种酶的有效抑制剂。在过去的十年中，基于氨基糖的葡糖神经酰胺合成酶抑制剂（这三种酶之一）受到了越来越多的关注，因为该酶在鞘糖脂生物合成中起着至关重要的作用。结合越来越多的病理过程与过量的鞘糖脂水平相关的事实，葡萄糖基神经酰胺合酶成为非常有吸引力的治疗和研究目标。我们在这里提出的结果证明，将亲脂部分从氮原子重新定位到1-deoxynojirimycin环系统上的其他位置不会导致更有效或更具选择性的葡糖神经酰胺合酶抑制剂。的β氮杂Ç糖苷类似物（17）保留了对葡糖神经酰胺合酶的最佳抑制效力，并且是比治疗剂N
• Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols
  作者：Rie Namme、Takashi Mitsugi、Hideyo Takahashi、Moto Shiro、Shiro Ikegami

  DOI：10.1016/j.tet.2006.07.032

  日期：2006.9

  A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely a-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by (3)J(C,H) coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective. (c) 2006 Elsevier Ltd. All rights reserved.