cyclohexyl 3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranoside | 63069-76-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cyclohexyl 3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranoside
• 英文别名: cyclohexyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranoside；[(2R,3S,4R,6S)-3,4-diacetyloxy-6-cyclohexyloxyoxan-2-yl]methyl acetate
• CAS: 63069-76-1
• 化学式: C₁₈H₂₈O₈
• 分子量: 372.416
• InChiKey: GWXAXDWFEWBWIY-BDXSIMOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 在 三甲基溴硅烷 、 氢溴酸 、 溶剂黄146 、 三苯基氧化膦 作用下， 以 二氯甲烷 为溶剂， -15.0~20.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 cyclohexyl 3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranoside
  参考文献：
  名称：

  TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals

  摘要：

  甘露糖醛酸盐的硫加成反应可以在无溶剂条件下高效地通过等物量的溴化三甲基硅(TMSBr)催化产生良好至优异收率的S-2-脱氧糖苷。此外，加入三苯基膦氧化物作为添加剂，TMSBr介导的甘露糖醛酸盐与多种醇类的直接糖基化反应具有高度α-选择性。

  DOI：

  10.3762/bjoc.12.164

文献信息

• GeCl₂·Dioxane–AgBF₄ Catalyzed Activation of Glycosyl Fluorides for Glycosylation
  作者：Qiuyu Zhu、Yu Tang、Biao Yu

  DOI：10.1021/acs.orglett.2c01146

  日期：2022.5.27

  catalytic glycosyl fluoride activation system using the GeCl2·dioxane–AgBF4 combination was developed, which involves a reversible activation of the anomeric C–F bond by a [Ge(II)–Cl]+ cation and a reversible chloride ion transfer between Ge(II) and glycosyl cations. This catalytic glycosylation system is easy to operate, proceeds at room temperature, and offers a broad scope of substrates.

  开发了一种使用 GeCl 2 ·二恶烷-AgBF 4组合的催化糖基氟化物活化系统，该系统涉及通过 [Ge(II)-Cl] +阳离子对异头 C-F 键的可逆活化和在它们之间的可逆氯离子转移。 Ge(II) 和糖基阳离子。这种催化糖基化系统易于操作，在室温下进行，并提供广泛的底物。
• α-Selective synthesis of 2-deoxy-glycosides and disaccharides
  作者：Guofang Yang、Xiaosheng Luo、Hong Guo、Qingbing Wang、Jiafen Zhou、Tianyun Huang、Jie Tang、Junjie Shan、Jianbo Zhang

  DOI：10.1080/07328303.2018.1439498

  日期：2018.3.24

  A metal-free catalytic method for the synthesis of 2-deoxy glycosides and disaccharides has been developed using stable 2-deoxy glucosyl and galactosyl acetate donors. They could react with a variety of acceptors in the presence of catalytic amount of TMSOTf at 0 degrees C to form glycosides, glycoconjugates, and disaccharides with excellent alpha-selectivity (> 19:1) and yields (up to 99%) in a short time (0.5 h). With this expedient method, several new compounds against human K562 and SMMC7721 cell lines were obtained and tested with in vitro antitumor bioactivities.
• Gallium reagents in organic synthesis: Dimethylgallium chloride and triflate as activators in glycosidation using glycopyranosyl fluorides
  作者：Susumu Kobayashi、Kazunori Koide、Masaji Ohno

  DOI：10.1016/s0040-4039(00)97382-9

  日期：1990.1