环己基葡萄糖苷 | 25320-98-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 环己基葡萄糖苷
• 英文名称: cyclohexyl glucoside
• 英文别名: cyclohexyl-α-D-glucopyranoside；Cyclohexyl-α-D-glucopyranosid；(2S,3R,4S,5S,6R)-2-cyclohexyloxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 25320-98-3
• 化学式: C₁₂H₂₂O₆
• 分子量: 262.303
• InChiKey: PUEQSGBQJWWOQJ-ZIQFBCGOSA-N

物化性质

• 熔点：
  124-125 °C
• 沸点：
  457.2±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-pyridyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 在 sodium methylate 、 mercury(II) nitrate 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 环己基葡萄糖苷
  参考文献：
  名称：

  Chemistry of the glycosidic linkage. Exceptionally fast and efficient formation of glycosides by remote activation

  摘要：

  DOI：

  10.1016/s0008-6215(00)84882-x

文献信息

• Bimodal Glycosyl Donors Protected by 2-<i>O-</i>(<i>ortho</i>-Tosylamido)benzyl Group
  作者：Feiqing Ding、Akihiro Ishiwata、Yukishige Ito

  DOI：10.1021/acs.orglett.8b01922

  日期：2018.7.20

  A glucosyl donor equipped with C2-o-TsNHbenzyl ether was shown to provide both α- and β-glycosides stereoselectivity, by changing the reaction conditions. Namely, β-glycosides were selectively obtained when the trichloroacetimidate was activated by Tf2NH. On the other hand, activation by TfOH in Et2O provided α-glycosides as major products. This “single donor” approach was employed to assemble naturally

  通过改变反应条件，显示了配备有C 2 -o- TsNH苄基醚的葡糖基供体同时提供α-和β-糖苷的立体选择性。即，当通过Tf 2 NH激活三氯乙酰亚胺酸酯时，选择性地获得β-糖苷。另一方面，通过TfOH在Et 2 O中的活化提供了α-糖苷作为主要产物。这种“单一供体”的方法被用来装配自然三糖α-发生d -Glc-（→2 1）-α- d -Glc-（1→6） - d -Glc和它的端基异构体。
• Protection-free Synthesis of Alkyl Glycosides under Hydrogenolytic Conditions
  作者：Masaki Ishihara、Yuka Takagi、Gefei Li、Masato Noguchi、Shin-ichiro Shoda

  DOI：10.1246/cl.130646

  日期：2013.10.5

  A convenient protection-free synthetic route for the preparation of alkyl glycosides has been developed. The alcoholysis of one-step preparable glycosyl donors, 4,6-dibenzyloxy-1,3,5-triazin-2-yl (DBT) glycosides, under hydrogenolytic conditions gave the corresponding glycosides in good yields without the addition of any acid promoters. The method could be successfully applied to the glycosylation of an acid-labile oligosaccharide.

  已开发出一种方便的无保护合成路线用于烷基糖苷的制备。在氢解条件下，一步可制备的糖苷供体4,6-二苯氧基-1,3,5-三嗪-2-基(DBT)糖苷的醇解反应，能够在不添加任何酸催化剂的情况下，以良好的产率得到相应的糖苷。该方法可以成功应用于酸不稳定的寡糖的糖基化。
• Ionic liquid promoted atom economic glycosylation under Lewis acid catalysis
  作者：Jacques Augé、Gwenaëlle Sizun

  DOI：10.1039/b904692e

  日期：——

  Straightforward glycosylation of various alcohols with unprotected and non-activated monosaccharides were performed under scandium triflate catalysis. Rate and yield of glycosylation were highly improved when using 1-butyl-3-methylimidazolium trifluoromethanesulfonate as a green solvent. This ionic liquid was allowed to be recycled at least three times without loss of activity. The possibility of drastically reducing the amounts of catalyst (down to 1 mol%) and aglycone (down to 1 equiv) when performing the reaction in ionic liquid opens new perspectives in O-glycosylation, as a direct coupling between an aglycone and free sugars.

  在钪三氟甲磺酸盐催化下，对各种醇与未保护和非活化的单糖进行了直接的糖苷化反应。当使用1-丁基-3-甲基咪唑三氟甲磺酸盐作为绿色溶剂时，糖苷化的反应速率和产率得到了显著提高。该离子液体可至少回收使用三次而不会失去活性。在离子液体中进行反应时，可以显著减少催化剂的用量（低至1 mol%）和糖苷的用量（低至1当量），这为O-糖苷化的直接耦合提供了新的前景，能够在糖苷和游离糖之间实现直接连接。
• Green glycosylation promoted by reusable biomass carbonaceous solid acid: an easy access to β-stereoselective terpene galactosides
  作者：Bala Kishan Gorityala、Jimei Ma、Kalyan Kumar Pasunooti、Shuting Cai、Xue-Wei Liu

  DOI：10.1039/c0gc00883d

  日期：——

  An efficient green protocol has been developed for the atom economic glycosylation of unprotected, unactivated glycosyl donors and glycosylation of glycosyl trichloroacetimidates with the aid of reusable eco-friendly biomass carbonaceous solid acid as catalyst.

  开发了一种高效的绿色协议，用于无保护、未活化的糖苷供体的原子经济糖苷化，以及在可重复使用的环保生物质碳酸固体酸催化剂的帮助下对糖苷三氯乙酰亚胺的糖苷化。
• Biphasic Catalysis with Disaccharide Phosphorylases: Chemoenzymatic Synthesis of α-<scp>d</scp>-Glucosides Using Sucrose Phosphorylase
  作者：Karel De Winter、Tom Desmet、Tim Devlamynck、Lisa Van Renterghem、Tom Verhaeghe、Helena Pelantová、Vladimír Křen、Wim Soetaert

  DOI：10.1021/op400302b

  日期：2014.6.20

  this work, a buffer/ethyl acetate ratio of 5:3 was identified to be the optimal solvent system, allowing the use of SP in biphasic systems. Careful optimization of the reaction conditions enabled the synthesis of a range of α-d-glucosides, such as cinnamyl α-d-glucopyranoside, geranyl α-d-glucopyranoside, 2-O-α-d-glucopyranosyl pyrogallol, and series of alkyl gallyl 4-O-α-d-glucopyranosides. The usefulness

  由于其广泛的受体特异性，蔗糖磷酸化酶（SP）已被用于将葡萄糖转移至多种受体分子。不幸的是，SP对这些受体的亲和力低（K m > 1 M）通常促使添加助溶剂，助溶剂通常不能溶解足够的底物或逐渐引起酶抑制和变性。在这项工作中，确定缓冲液/乙酸乙酯的比例为5：3是最佳溶剂系统，从而允许在双相系统中使用SP。的反应条件的仔细优化启用的范围α-的合成d -glucosides，如肉桂α- d吡喃葡萄糖苷，香叶基α- d吡喃葡萄糖苷，2- ö-α- d吡喃葡萄糖基邻苯三酚，和烷基gallyl 4-系列ö -α- d -glucopyranosides。通过在辅助溶剂和双相反应系统中比较邻苯三酚的葡萄糖基化进一步说明了双相催化的有用性。前者的受体收率仅达到17.4％，而使用双相催化时，大约60％的初始邻苯三酚会转化。