3,4,6-Tri-O-benzyl-2-deoxy-2-phenylthio-α-D-glucopyranose | 117901-42-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4,6-Tri-O-benzyl-2-deoxy-2-phenylthio-α-D-glucopyranose
• 英文别名: 3,4,6-tri-O-benzyl-2-deoxy-2-(phenylthio)-α-D-glucose；(2S,3R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-3-phenylsulfanyloxan-2-ol
• CAS: 117901-42-5
• 化学式: C₃₃H₃₄O₅S
• 分子量: 542.696
• InChiKey: GCYHIZPYVVSMSC-AALIFHQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4,6-Tri-O-benzyl-2-deoxy-2-phenylthio-α-D-glucopyranose 在 4 A molecular sieve 、 三氟化硼乙醚 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-[(3S,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yloxy]-5-phenylsulfanyl-tetrahydro-pyran
  参考文献：
  名称：

  A Convenient Synthesis of 2-Deoxy-β-D-glucopyranosides

  摘要：

  O-(2-脱氧-2-苯硫基-α-D-吡喃葡萄糖基)三氯乙酰亚胺酯α-3 是通过两步从 3,4,6-三-O-苄基-D-葡萄糖 (1) 获得的程序。该化合物是一种强大的吡喃葡萄糖基供体，它与典型的醇受体主要提供相应的2-苯硫基取代的2-脱氧-β-D-吡喃葡萄糖苷β-5a 至β-5d。这些通过雷尼镍处理以高产率转化为所需的2-脱氧-β-D-吡喃葡萄糖苷6。

  DOI：

  10.1055/s-1988-27673
• 作为产物：
  描述：

  3,4,6-三苄氧基-D-葡萄烯糖 、 苯次磺酰氯 在 sodium carbonate 作用下， 生成 3,4,6-Tri-O-benzyl-2-deoxy-2-phenylthio-α-D-glucopyranose
  参考文献：
  名称：

  A Convenient Synthesis of 2-Deoxy-β-D-glucopyranosides

  摘要：

  O-(2-脱氧-2-苯硫基-α-D-吡喃葡萄糖基)三氯乙酰亚胺酯α-3 是通过两步从 3,4,6-三-O-苄基-D-葡萄糖 (1) 获得的程序。该化合物是一种强大的吡喃葡萄糖基供体，它与典型的醇受体主要提供相应的2-苯硫基取代的2-脱氧-β-D-吡喃葡萄糖苷β-5a 至β-5d。这些通过雷尼镍处理以高产率转化为所需的2-脱氧-β-D-吡喃葡萄糖苷6。

  DOI：

  10.1055/s-1988-27673

文献信息

• A Stereocontrolled Construction of 2-Deoxy-β-glycosidic Linkages<i>via</i>1,2-<i>trans</i>-β-Glycosidation of 2-Deoxy-2-[(<i>p</i>-methoxyphenyl)thio] glycopyranosyl<i>N</i>,<i>N</i>,<i>N</i>′,<i>N</i>′-Tetramethylphosphoroamidates
  作者：Shun-ichi Hashimoto、Yuki Yanagiya、Takeshi Honda、Shiro Ikegami

  DOI：10.1246/cl.1992.1511

  日期：1992.8

  A stereocontrolled synthesis of 2-deoxy-β-glycosides has been achieved by developing a salient 1,2-trans-glycosidation method with 2-deoxy-2-[(p-methoxyphenyl)thio]glycopyranosyl N,N,N′,N′-tetramethylphosphoroamidates as glycosyl donors followed by a reductive removal of the p-methoxyphenylthio group with Raney nickel. The p-methoxyphenylthio group equatorially disposed at C-2 has proven to be an excellent stereodirecting auxiliary.

  通过开发一种显著的1,2-反式糖基化方法，使用2-脱氧-2-[(对甲氧基苯基)硫]吡喃糖基N,N,N',N'-四甲基膦酰胺作为糖基供体，随后用Raney镍还原去除对甲氧基苯硫基团，实现了2-脱氧-β-糖苷的立体控制合成。位于C-2位的对甲氧基苯硫基团在赤道位置上被证明是一个极佳的立体导向辅助基团。
• Arylbis(arylthio)sulfonium salts as reagents for the synthesis of 2-deoxy-.beta.-glycosides
  作者：Gurmit Grewal、Neelu Kaila、Richard W. Franck

  DOI：10.1021/jo00033a033

  日期：1992.3

  The title sulfonium salts undergo electrophilic addition to glycals in the presence of alcohols to form principally beta-glycosides. A substituent effect study has shown that the reagent with a p-tolylthio group is the most face-selective. By variation of the alcohol nucleophile, it has been shown that face selectivity is also dependent on the structure of the nucleophile. One instance of double diastereodifferentiation was uncovered when the racemic alcohol 23.5 was used in a reaction with tribenzyl glucal 22.1. The effect of glycal substitution on the face selectivity has led to the postulation of a heretofore unrecognized and still unexplained stereoelectronic effect.