Glycosylation of Stannyl Ceramides Promoted by Modified Montmorillonite in Supercritical Carbon Dioxide

被引:3
作者
Antonio Morales-Serna, Jose [1 ]
Nguyen, Bao N. [2 ]
Garcia-Rios, Erendira [3 ]
Gavino, Ruben [3 ]
Cardenas, Jorge [3 ]
Garcia de la Mora, Gustavo [4 ]
机构
[1] Univ Autonoma Metropolitana Iztapalapa, Dept Quim, Av San Rafael Atlixco 186, Ciudad De Mexico 09340, Mexico
[2] Univ Leeds, Sch Chem, Leeds LS2 9JT, W Yorkshire, England
[3] Univ Nacl Autonoma Mexico, Inst Quim, Ciudad Univ, Ciudad De Mexico 04510, Mexico
[4] Univ Nacl Autonoma Mexico, Dept Quim Organ, Fac Quim, Ciudad Univ, Ciudad De Mexico 04510, Mexico
来源
SYNTHESIS-STUTTGART | 2018年 / 50卷 / 03期
关键词
glycosylation; beta-glycolipids; iGB3; supercritical carbon dioxide; montmorillonite; FLUID EXTRACTION; GREEN SOLVENTS; ACID; GLYCOSIDATION; CATALYSIS; SUGAR; CO2; GLYCOLIPIDS; SOLUBILITY; EFFICIENT;
D O I
10.1055/s-0036-1591515
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The direct glycosylation of ceramides in supercritical carbon dioxide (scCO(2)) successfully proceeded to produce beta-glycolipids in high yield and with full stereoselectivity. The reaction is promoted by montmorillonite modified with a superacid (CF3SO3H). The value of this protocol was demonstrated in the efficient synthesis of isoglobotrihexosylceramide (iGB(3)).
引用
收藏
页码:593 / 598
页数:6
相关论文
共 46 条
[31]   A novel procedure for the isolation of glycolipids from Bifidobacterium adolescentis 94 BIM using supercritical carbon dioxide [J].
Novik, G ;
Gamian, A ;
Francisco, JD ;
Dey, ES .
JOURNAL OF BIOTECHNOLOGY, 2006, 121 (04) :555-562
[32]   Homogeneous Metal-Based Catalysis in Supercritical Carbon Dioxide as Reaction Medium [J].
Olmos, Andrea ;
Asensio, Gregorio ;
Perez, Pedro J. .
ACS CATALYSIS, 2016, 6 (07) :4265-4280
[33]   Supercritical carbon dioxide: a solvent like no other [J].
Peach, Jocelyn ;
Eastoe, Julian .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 :1878-1895
[34]   An Alternative Reaction Course in O-Glycosidation with O-Glycosyl Trichloroacetimidates as Glycosyl Donors and Lewis Acidic Metal Salts as Catalyst: Acid-Base Catalysis with Gold Chloride-Glycosyl Acceptor Adducts [J].
Peng, Peng ;
Schmidt, Richard R. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (39) :12653-12659
[35]   Peracetylated sugar derivatives show high solubility in liquid and supercritical carbon dioxide [J].
Potluri, VK ;
Xu, JH ;
Enick, R ;
Beckman, E ;
Hamilton, AD .
ORGANIC LETTERS, 2002, 4 (14) :2333-2335
[36]   Application of supercritical carbon dioxide(scCO2) for the extraction of glycolipids from Lactobacillus plantarum B-01 [J].
Rakhuba, Dzianis ;
Novik, Galina ;
Dey, Estera Szwajcer .
JOURNAL OF SUPERCRITICAL FLUIDS, 2009, 49 (01) :45-51
[37]   Mechanism of Chemical Glycosylation: Focus on the Mode of Activation and Departure of Anomeric Leaving Groups [J].
Ranade, Sneha C. ;
Demchenko, Alexei V. .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 2013, 32 (01) :1-43
[38]   Polar attributes of supercritical carbon dioxide [J].
Raveendran, P ;
Ikushima, Y ;
Wallen, SL .
ACCOUNTS OF CHEMICAL RESEARCH, 2005, 38 (06) :478-485
[39]   Sugar acetates as novel, renewable CO2-philes [J].
Raveendran, P ;
Wallen, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (25) :7274-7275
[40]   Supercritical Fluid Extraction Using CO2: Main Applications and Future Perspectives [J].
Souza Machado, Bruna Aparecida ;
Pereira, Camila Gambini ;
Nunes, Silmar Baptista ;
Padilha, Francine Ferreira ;
Umsza-Guez, Marcelo Andres .
SEPARATION SCIENCE AND TECHNOLOGY, 2013, 48 (18) :2741-2760