cyclohexyl 2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranoside | 69247-28-5

• 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 2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranoside
• 英文别名: cyclohexyl 3,4,6-tri-O-acetyl-2-deoxy-D-galactopyranoside；[(2R,3R,4R,6S)-3,4-diacetyloxy-6-cyclohexyloxyoxan-2-yl]methyl acetate
• CAS: 69247-28-5
• 化学式: C₁₈H₂₈O₈
• 分子量: 372.416
• InChiKey: GWXAXDWFEWBWIY-ZJPYXAASSA-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：

  beta-D-半乳糖五乙酸酯 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 2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranoside
  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

• Perfluorophenylboronic acid-catalyzed direct α-stereoselective synthesis of 2-deoxygalactosides from deactivated peracetylated <scp>d</scp>-galactal
  作者：Madhu Babu Tatina、Ziad Moussa、Mengxin Xia、Zaher M. A. Judeh

  DOI：10.1039/c9cc06151g

  日期：——

  Perfluorophenylboronic acid 1c catalyzes the direct stereoselective addition of alcohol nucleophiles to deactivated peracetylated d-galactal to give 2-deoxygalactosides in 55-88% yield with complete α-selectivity. The unprecedented results reported here also enable the synthesis of disaccharides containing the 2-deoxygalactose moiety directly from the deactivated peracetylated d-galactal. This convenient and metal-free

  全氟苯基硼酸1c催化将醇亲核试剂直接立体选择性加成到失活的过乙酰化d-半乳糖上，以55-8％的收率得到2-deoxygalactosides，具有完全的α-选择性。这里报道的空前的结果还使得能够直接从失活的过乙酰化的d-半乳糖合成包含2-脱氧半乳糖部分的二糖。这种方便且无金属的糖基化方法可与多种醇亲核试剂作为受体配合使用，并能耐受多种官能团，而不会形成Ferrier副产物，也无需大量过量的亲核试剂或添加剂。该方法对于合成多种α-2-脱氧半乳糖苷可能是有用的。
• Catalytic ceric ammonium nitrate mediated synthesis of 2-deoxy-1-thioglycosides
  作者：Somak Paul、Narayanaswamy Jayaraman

  DOI：10.1016/j.carres.2004.07.010

  日期：2004.9

  Synthesis of 2-deoxy-1-thioglycosides from glycals, mediated by catalytic amounts of ceric ammonium nitrate is reported. Apart from the 2-deoxy-1-thioglycosides, formation of the 2,3-unsaturated enose, corresponding to the Ferrier product, is also observed, especially for the glucal substrates. A radical oxocarbenium ion and a thiolate intermediates are most likely to mediate the reaction. Upon synthesis

  据报道由催化量的硝酸铈铵介导的由糖类合成2-脱氧-1-硫代糖苷。除了2-脱氧-1-硫代糖苷以外，还观察到形成了对应于Ferrier产物的2,3-不饱和烯键，特别是对于葡萄糖底物。氧羰基自由基离子和硫醇盐中间体最有可能介导该反应。在合成2-脱氧-1-硫代糖苷时，几乎没有与糖基和糖基受体一起进行代表性的糖基化反应，并且仅获得α-异头2-脱氧糖苷。
• Ferrier Rearrangement and 2-Deoxy Sugar Synthesis from d-Glycals Mediated by Layered α-Zirconium Sulfophenylphosphonate-Methanphosphonate as Heterogeneous Catalyst
  作者：Ornelio Rosati、Massimo Curini、Federica Messina、Maria Carla Marcotullio、Giancarlo Cravotto

  DOI：10.1007/s10562-012-0932-z

  日期：2013.2

  conditions in short time and good yields. Notably, the combination of α-zirconium sulfophenylphosphonate-methanphosphonate and lithium bromide change the regioselectivity of this process affording 2-deoxy sugars in good yields.Graphical Abstract

  层状 α-磺基苯基膦酸锆 - 甲膦酸是一种固体酸催化剂，可在温和的反应条件下，在短时间内和良好的产率催化 d-乙二醇和醇类亲核试剂的费里尔重排。值得注意的是，α-磺基苯基膦酸锆-甲膦酸锆和溴化锂的组合改变了该过程的区域选择性，以良好的收率提供了 2-脱氧糖。
• 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.
• Dehydrative glycosidations of 2-deoxysugar derivatives catalyzed by an arylboronic ester
  作者：Sanjay Manhas、Mark S. Taylor

  DOI：10.1016/j.carres.2018.10.002

  日期：2018.12

  An N-methylpyridinium-4-boronic ester acts as a catalyst for dehydrative glycosidations of 2-deoxy sugar-derived hemiacetals. The catalytic protocol is tolerant of functionalized acceptors, including alcohols bearing isopropylidene ketal, tert-butyl carbamate or benzyl carbamate groups. The results demonstrate that organoboron- catalyzed substitution reactions of alcohols, which have previously been conducted on p-activated (benzylic, allylic or propargylic) substrates, can also be used to achieve C-O bond formation from carbohydratederived hemiacetals.