168037-64-7Relevant academic research and scientific papers
Total Synthesis of the Repeating Unit of Streptococcus pneumoniae Zwitterionic Polysaccharide Sp1
Ghosh, Antara,Kulkarni, Suvarn S.
, p. 18292 - 18299 (2021/12/13)
Reported herein is the total synthesis of the trisaccharide repeating unit of Streptococcus pneumoniae zwitterionic polysaccharide Sp1 containing a rare sugar, 2-acetamido-4-amino-2,4,6-trideoxy-d-galactose (AAT), and three consecutive 1,2-cis-glycosidic linkages. The total synthesis was completed via highly stereoselective glycosylations and late-stage oxidation as key steps involving a longest linear sequence of 21 steps with 4.4% overall yield.
C-Glycosyl amino acids through hydroboration-cross-coupling of exo-glycals and their application in automated solid-phase synthesis
Koch, Stefan,Schollmeyer, Dieter,L?we, Holger,Kunz, Horst
supporting information, p. 7020 - 7041 (2013/07/05)
O-Glycosylation is one of the most important post-translational modifications of proteins. The attachment of carbohydrates to the peptide backbone influences the conformation as well as the solubility of the conjugates and can even be essential for binding to specific ligands in cell-cell interactions or for active transport over membranes. This makes glycopeptides an interesting class of compounds for medical applications. To enhance the long-term availability of these molecules in vivo, the stabilization of the glycosidic bond between the amino acid residue and the carbohydrate is of interest. The described modular approach affords β-linked C-glycosyl amino acids by a sequence of Petasis olefination of glyconolactones, stereoselective hydroboration and a mild B-alkyl-Suzuki coupling reaction. The coupling products were transformed to C-glycosyl amino acid building-blocks suitable for solid-phase synthesis and successfully incorporated into a partial sequence of the tumor-associated MUC1-glycopeptide. The resulting C-glycopeptides are candidates for the development of long-term stable mimics of O-glycopeptide vaccines. Copyright
Glycosylation catalyzed by a chiral bronsted acid
Cox, Daniel J.,Smith, Martin D.,Fairbanks, Antony J.
supporting information; experimental part, p. 1452 - 1455 (2010/06/20)
"Chemical equation presented" The use of a chiral Bronsted acid catalyst for the activation of trichloroacetimidate glycosyl donors has been demonstrated for the first time. In toluene the chirality of the acid catalyst is seen to influence the stereochem
A mild and general method for preparation of α-glycosyl chlorides
Chang, Chih-Wei,Chang, Shih-Sheng,Chao, Chin-Sheng,Mong, Kwok-Kong T.
supporting information; experimental part, p. 4536 - 4540 (2009/12/03)
A mild and efficient chlorination method for production of glycosyl chlorides is first described which employs inexpensive trichlorotriazine (TCT) and DMF as a chlorination reagent and is compatible with typical acid-labile hydroxyl protecting functions. The scope and limitations, reaction mechanism and its application in the sequential glycosylations are discussed.
Total synthesis of α-galactosyl cerebroside
Figueroa-Perez, Santiago,Schmidt, Richard R.
, p. 95 - 102 (2007/10/03)
A highly convergent synthetic approach was developed to obtain α- galactosyl cerebroside O-(α-D-galactopyranosyl)-2-hexacosylamino-D-ribo- 1,3,4-octadecantriol, which has previously been demonstrated to have immunostimulatory activity. Known 4,6-O-benzyli
Stereochemical Control in Hex-5-enyl Radical Cyclizations: From Carbohydrates to Carbocycles. 3
RajanBabu, T. V.,Fukunaga, Tadamichi,Reddy, G. S.
, p. 1759 - 1769 (2007/10/02)
The hex-5-enyl radical cyclization reaction was applied to prepare highly oxygenated cyclopentanoids from aldopyranose sugars.The Wittig reaction of the sugars readily provides hex-5-en-1-ols which were converted to hex-5-enyl radicals via one of the vari
