2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl N-phenyltrifluoroacetimidate | 1228757-57-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl N-phenyltrifluoroacetimidate
• 英文别名: 2,3,4-tri-O-benzyl-β-D-glucopyranosyl N-phenyltrifluoroacetimidate；N-phenyl-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl) trifluoroacetimidate；[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] 2,2,2-trifluoro-N-phenylethanimidate
• CAS: 1228757-57-0
• 化学式: C₄₂H₄₀F₃NO₆
• 分子量: 711.778
• InChiKey: BJCRNHIPUWZUPQ-DTQLOPILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  52
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  苯胺 在 四氯化碳 、 15-冠醚-5 、 sodium hydride 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 7.58h， 生成 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl N-phenyltrifluoroacetimidate
  参考文献：
  名称：

  N-Aryl-O-glycosyl Haloacetimidates as Glycosyl Donors

  摘要：

  Reaction of 1-O-unprotected tetra-O-acetyl- and tetra-O-benzyl-glucopyranose with N-aryl haloacetimidoyl chlorides in the presence of sodium hydride and 15-crown-5 afforded N-aryl-O-glucopyranosyl haloacetimidates. Mainly the -anomers were obtained in this anomeric O-acylation-type reaction. The glycosyl donor properties of these haloacetimidates were investigated with 6-O- and 4-O-unprotected glucopyranosides as acceptors. The results were compared with those obtained with the corresponding O-glucopyranosyl trichloroacetimidates as glycosyl donors and the same acceptors. It was found that N-(2-chloro-6-methylphenyl)-O-glucopyranosyl trifluoroacetimidates (16Ad, 16Bd) exhibit glycosyl donor properties closely related to those of the corresponding N-unsubstituted O-glucopyranosyl trichloroacetimidates (12A, 12B).

  DOI：

  10.1080/07328301003597673

文献信息

• Regenerative Glycosylation under Nucleophilic Catalysis
  作者：Swati S. Nigudkar、Keith J. Stine、Alexei V. Demchenko

  DOI：10.1021/ja411746a

  日期：2014.1.22

  This article describes 3,3-difluoroxindole (HOFox)-mediated glycosylation. The uniqueness of this approach is that both the in situ synthesis of 3,3-difluoro-3H-indol-2-yl (OFox) glycosyl donors and activation thereof can be conducted in a regenerative fashion as is a typical reaction performed under nucleophilic catalysis. Only a catalytic amount of the OFox imidate donor and a Lewis acid activator are present in the reaction medium. The OFox imidate donor is constantly regenerated upon its consumption until glycosyl acceptor has reacted.
• <i>N</i>-Aryl-<i>O</i>-glycosyl Haloacetimidates as Glycosyl Donors
  作者：Uschi Huchel、Pallavi Tiwari、Richard R. Schmidt

  DOI：10.1080/07328301003597673

  日期：2010.3.22

  Reaction of 1-O-unprotected tetra-O-acetyl- and tetra-O-benzyl-glucopyranose with N-aryl haloacetimidoyl chlorides in the presence of sodium hydride and 15-crown-5 afforded N-aryl-O-glucopyranosyl haloacetimidates. Mainly the -anomers were obtained in this anomeric O-acylation-type reaction. The glycosyl donor properties of these haloacetimidates were investigated with 6-O- and 4-O-unprotected glucopyranosides as acceptors. The results were compared with those obtained with the corresponding O-glucopyranosyl trichloroacetimidates as glycosyl donors and the same acceptors. It was found that N-(2-chloro-6-methylphenyl)-O-glucopyranosyl trifluoroacetimidates (16Ad, 16Bd) exhibit glycosyl donor properties closely related to those of the corresponding N-unsubstituted O-glucopyranosyl trichloroacetimidates (12A, 12B).