propargyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside | 194088-19-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: propargyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-2-ynoxyoxane
• CAS: 194088-19-2
• 化学式: C₃₇H₃₈O₆
• 分子量: 578.705
• InChiKey: ATGYINYFSVYATO-MANRWTMFSA-N

物化性质

• 沸点：
  693.8±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  propargyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 在 potassium carbonate 、 重水 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以99%的产率得到(2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(3-deuteroprop-2-ynyloxy)tetrahydro-2H-pyran
  参考文献：
  名称：

  Mild Reaction Conditions for the Terminal Deuteration of Alkynes

  摘要：

  Routinely employed syntheses of terminally deuterated alkynes often utilize strong bases (i.e., LDA, n-BuLi, or Grignard reagents) or low (i.e., -78 degrees C) or elevated (i.e., 56 degrees C) reaction temperatures; furthermore many of these procedures afford average yields and in some cases less than optimum deuterium incorporation. Herein we report the application of alternative extremely mild reaction conditions that readily afford quantitative yields of terminally deuterated alkynes in a matter of minutes with exceptional isotope incorporation at ambient temperature.

  DOI：

  10.1021/ol2029178
• 作为产物：
  描述：

  propargyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 在 gold(III) bromide 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以51%的产率得到propargyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  2-C-支链碳水化合物的金催化反应：轻度糖苷化和选择性异构化

  摘要：

  2-C-支链甲基糖苷在金催化下与各种醇反应生成转糖基化产物。该方法适用于方便的双糖合成。在没有亲核试剂的情况下，会发生选择性异构化，从而首先获得 α-构型的 2-C-硝基甲基糖苷。结果对于金催化糖苷化的机制很有趣。

  DOI：

  10.1002/ejoc.201100134

文献信息

• Propargyl Glycosides as Stable Glycosyl Donors:  Anomeric Activation and Glycoside Syntheses
  作者：Srinivas Hotha、Sudhir Kashyap

  DOI：10.1021/ja062425c

  日期：2006.8.1

  The advantages of stable glycosyl donors for saccharide coupling are many, and we describe herein the utility of propargyl glycosides for anomeric activation and glycoside synthesis exploiting the alkynophilicity of AuCl3. Various aglycones were reacted with propargyl glycosides, resulting in the formation of an α,β-mixture of glycosides and disaccharides in good yields.

  用于糖偶联的稳定糖基供体的优点有很多，我们在本文中描述了炔丙基糖苷在利用 AuCl 3 的亲炔性进行异头活化和糖苷合成中的用途。各种苷元与炔丙基糖苷反应，以良好的产率形成糖苷和二糖的α,β-混合物。
• Click Inspired Synthesis of 1,2,3-Triazole-linked 1,3,4-Oxadiazole Glycoconjugates
  作者：Divya Kushwaha、Vinod K. Tiwari

  DOI：10.1002/jhet.2845

  日期：2017.7

  azide–alkyne cycloaddition. A series of glycosyl alkynes 1b–i, obtained from various commercial sugars, were treated with azide functionalized 1,3,4‐oxadiazole using click chemistry to access triazole‐linked glycosylated 1,3,4‐oxadiazoles 10b–i in good yields. The structure of the developed glycoconjugates has been ascertained by extensive spectroscopic analysis (1H &13C NMR, IR, and MS).

  通过Cu（I）催化的叠氮化物-炔烃环加成反应描述了具有生物学优势的1,3,4-恶二唑支架的糖缀合。使用叠氮化物官能化的1,3,4-恶二唑，通过单击化学处理，将从叠氮化物官能化的1,3,4-恶二唑中得到的一系列糖基炔1b – i，以高收率获得三唑连接的糖基化的1,3,4-恶二唑10b – i。已通过广泛的光谱分析（1 H和13 C NMR，IR和MS）确定了开发的糖缀合物的结构。
• Substoichiometric FeCl3 Activation of Propargyl Glycosides for the Synthesis of Disaccharides and Glycoconjugates
  作者：Jianbo Zhang、Guosheng Sun、Yue Wu、Anqi Liu、Saifeng Qiu、Wan Zhang、Zhongfu Wang

  DOI：10.1055/s-0036-1591525

  日期：2018.3

  Glycosides as glycosyl donors using FeCl3 have been described. Under optimal reaction conditions, three kinds of propargyl glycosides were found to react with steroids and sugar-derived glycosyl acceptors to afford the corresponding disaccharides and glycoconjugates in good to excellent yields (66–91%). Meanwhile, the method can also realize one-pot synthesis of disaccharides, making it an effective

  已经描述了使用 FeCl3 作为糖基供体的糖苷。在最佳反应条件下，发现三种炔丙基糖苷与类固醇和糖衍生的糖基受体反应，以良好至极好的收率（66-91%）提供相应的二糖和糖缀合物。同时，该方法还可实现双糖的一锅法合成，是一种高效、经济、绿色的糖基化方法。
• Gold mediated glycosylations: selective activation of propargyl 1,2-orthoesters in the presence of aglycones containing a propargyl moiety
  作者：Gopalsamy Sureshkumar、Srinivas Hotha

  DOI：10.1039/b806707d

  日期：——

  Selective activation of propargyl 1,2-orthoesters in the presence of propargyl glycosides and propargyl ethers was studied; a catalytic amount of AuBr3 activated the propargyloxy group of the 1,2-orthoester thereby giving access to disaccharides with the propargyl group at the reducing end; furthermore, propargyl ethers were unaffected under the reaction conditions.

  在存在炔丙基糖苷和炔丙基醚的情况下，对炔丙基1,2-邻酯的选择性活化进行了研究；少量AuBr3催化剂可活化1,2-邻酯的炔丙氧基团，从而获得在还原端具有炔丙基团的双糖；此外，在反应条件下炔丙基醚不受影响。
• Tris(pentafluorophenyl)borane-Promoted Stereoselective Glycosylation with Glycosyl Trichloroacetimidates under Mild Conditions
  作者：Kunj Bihari Mishra、Adesh Kumar Singh、Jeyakumar Kandasamy

  DOI：10.1021/acs.joc.8b00215

  日期：2018.4.6

  Tris(pentafluorophenyl)borane-promoted stereoselective glycosylation with trichloroacetimidate glycosyl donors is described. The reactions proceed efficiently with a wide range of acceptors, from sugar to nonsugar, under mild conditions in the presence of a catalytic amount of B(C6F5)3. The perbenzylated glucosyl α-imidate provides β-selective glycosides in 70–92% yields.

  描述了用三氯乙酰亚胺酸酯糖基供体的三（五氟苯基）硼烷促进的立体选择性糖基化。在催化量的B（C 6 F 5）3存在下，在温和条件下，反应可利用各种受体（从糖到非糖）有效地进行。过苄基化的葡萄糖基α-亚氨酸酯以70-92％的产率提供β-选择性糖苷。