152964-70-0Relevant articles and documents
Synthesis of Glucuronoxylan Hexasaccharides by Preactivation-Based Glycosylations
B?hm, Maximilian,Madsen, Robert,Underlin, Emilie N.,d'Errico, Clotilde
supporting information, (2020/05/16)
The synthesis of two glucuronoxylans is described, which both consist of a pentaxylan backbone and a glucuronic acid linked to the 2 position in the fourth xylose residue from the reducing end. The two target molecules differ in the 4 position of the glucuronic acid where one is unsubstituted while the other contains a methyl ether. The pentaxylan backbone is assembled in four glycosylation reactions with phenyl thioglycoside donors. The couplings are performed by preactivation of the donor with in-situ-generated p-nitrobenzenesulfenyl triflate prior to addition of the acceptor. The glucuronic acids are then attached by Koenigs-Knorr glycosylations followed by deprotections. The syntheses employ a total of 8 steps from monosaccharide building blocks and afford the two glucuronoxylans in 12 and 15 % overall yield. The hexasaccharide products are valuable substrates for investigating the activity and specificity of glucuronoxylan-degrading enzymes.
Picoloyl protecting group in synthesis: Focus on a highly chemoselective catalytic removal
Bandara, Mithila D.,Demchenko, Alexei V.,Geringer, Scott A.,Mannino, Michael P.
, p. 4863 - 4871 (2020/07/13)
The picoloyl ester (Pico) has proven to be a versatile protecting group in carbohydrate chemistry. It can be used for the purpose of stereocontrolling glycosylations via an H-bond-mediated Aglycone Delivery (HAD) method. It can also be used as a temporary protecting group that can be efficiently introduced and chemoselectively cleaved in the presence of practically all other common protecting groups used in synthesis. Herein, we will describe a new method for rapid, catalytic, and highly chemoselective removal of the picoloyl group using inexpensive copper(ii) or iron(iii) salts. This journal is
High-yield total synthesis of (-)-strictinin through intramolecular coupling of gallates
Michihata, Naoki,Kaneko, Yuki,Kasai, Yusuke,Tanigawa, Kotaro,Hirokane, Tsukasa,Higasa, Sho,Yamada, Hidetoshi
, p. 4319 - 4328 (2013/06/27)
This paper describes a total synthesis of (-)-strictinin, an ellagitannin that is 1-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl (HHDP)-β-d-glucose. In the study, total efficiency of the synthesis was improved to produce a 78% overall yield in 13 steps from d-glucose. In the synthesis, formation of the 4,6-(S)-HHDP bridge including the 11-membered bislactone ring was a key step, in which intramolecular aryl-aryl coupling was adopted. The coupling was oxidatively induced by CuCl2-n-BuNH2 with perfect control of the axial chirality, and the reaction conditions of this coupling were optimized thoroughly to achieve the quantitative formation of the bridge.
4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene] acetals. Improved second-generation acetals for the stereoselective formation of β-D-mannopyranosides and regioselective reductive radical fragmentation to β-D-rhamnopyranosides. Scope and limitations
Crich, David,Bowers, Albert A.
, p. 3452 - 3463 (2007/10/03)
The [1-cyano-2-(2-iodophenyl)]ethylidene group is introduced as an acetal-protecting group for carbohydrate thioglycoside donors. The group is easily introduced under mild conditions, over short reaction times, and in the presence of a wide variety of oth
Influence of the 4,6-O-benzylidene, 4,6-O-phenylboronate, and 4,6-O-polystyrylboronate protecting groups on the stereochemical outcome of thioglycoside-based glycosylations mediated by 1-benzenesulfinyl piperidine/triflic anhydride and N-iodosuccinimide/t
Crich, David,De la Mora, Marco,Vinod
, p. 8142 - 8148 (2007/10/03)
The effect of 4,6-O-benzylidene acetals, 4,6-O-phenylboronate esters, and 4,6-O-polystyrylboronate esters on the stereoselectivity of couplings to galacto-, gluco-, and mannopyranosyl thioglycosides, otherwise protected with benzyl ethers, has been invest
Synthesis of neomycin analogs to investigate aminoglycoside-RNA interactions
Seeberger, Peter H.,Baumann, Michael,Zhang, Guangtao,Kanemitsu, Takuya,Swayze, Eric E.,Hofstadler, Steven A.,Griffey, Richard H.
, p. 1323 - 1326 (2007/10/03)
A series of novel aminoglycoside oligosaccharide analogs containing a 2,5-dideoxystreptamine core scaffold was prepared to study aminoglycoside binding to the small subunit of 16S rRNA. A set of monosaccharide building blocks carrying amino groups in diff
A two-directional approach for the solid-phase synthesis of trisaccharide libraries
Zhu, Tong,Boons, Geert-Jan
, p. 1898 - 1900 (2007/10/03)
Without protecting groups, polymer-bound thioglycosyl sugars can undergo two successive glycosylation reactions, once as a donor and once as an acceptor, to give trisaccharides such as 1. Trisaccharide libraries prepared by this strategy have a known suga
The Stereoselective Synthesis of Cyclomaltopentaose. A Novel Cyclodextrin Homologue with D.P. Five.
Nakagawa, Toshio,Ueno, Koji,Kashiwa, Mariko,Watanabe, Junko
, p. 1921 - 1924 (2007/10/02)
A key intermediate 15 was prepared via successive glycosidations of 1,6-anhydro maltose derivative 8 with glycosyl donors 6 and then with 11, cyclized under a diluted condition, and deprotected to give the title compound.Every glycosidation, including the
PARTIAL SUBSTITUTION OF THIOGLYCOSIDES BY PHASE TRANSFER CATALYZED BENZOYLATION AND BENZYLATION
Garegg, Per J.,Kvarnstroem, Ingemar,Niklasson, Annika,Niklasson, Gunilla,Svensson, Stefan C. T.
, p. 933 - 954 (2007/10/02)
Partial substitution by phase transfer catalysis giving monobenzoylated and monobenzylated products from 2,3- and from 4,6-diols in ethyl 1-thio-D-hexopyranosides with the β-gluco, β-galacto- and α-manno-configurations are described.Two disaccharide thiog
