23262-80-8Relevant academic research and scientific papers
Dimerization of aldosuloses and aldonolactones into branched higher carbon sugars
Zhao, Yachen,Wang, Shengyang,Yu, Biao
supporting information, p. 2020 - 2022 (2020/02/22)
Homo-dimerizations of a variety of aldosulose and aldonolactone derivatives via aldol and Claisen reactions have been achieved, leading to novel branched higher carbon sugars in a highly stereoselective manner.
Synthesis and use of 6,6,6-trifluoro-L-fucose to block core-fucosylation in hybridoma cell lines
McKenzie, Nicole C.,Scott, Nichollas E.,John, Alan,White, Jonathan M.,Goddard-Borger, Ethan D.
, p. 4 - 9 (2018/06/06)
Many monoclonal antibodies (mAbs) used in cancer immunotherapy mediate tumour cell lysis by recruiting natural killer (NK) cells; a phenomenon known as antibody-dependent cellular cytotoxicity (ADCC). Eliminating core-fucose from the N-glycans of a mAb enhances its capacity to induce ADCC. As such, inhibitors of fucosylation are highly desirable for the production of mAbs for research and therapeutic use. Herein, we describe a simple synthesis of 6,6,6-trifluoro-L-fucose (F3Fuc), a metabolic inhibitor of fucosylation, and demonstrate the utility of this molecule in the production of low-fucose mAbs from murine hybridoma cell lines.
C-Triazolyl β-d-furanosides as LpxC inhibitors: Stereoselective synthesis and biological evaluation
Jana, Sunit Kumar,L?ppenberg, Marius,Daniliuc, Constantin G.,Holl, Ralph
, p. 6569 - 6577 (2015/03/30)
C-Triazolyl β-d-furanosides 10a-f were synthesized in a stereocontrolled way, starting from d-mannose. In the key steps of the synthesis a diastereoselective reduction of hemiketal 14 and a Cu(I) catalyzed [3+2]-cycloaddition of central building block 18
Synthesis of C-spiro-glycoconjugates from sugar lactones via zinc mediated Barbier reaction
Lambu, Mallikharjuna Rao,Hussain, Altaf,Sharma, Deepak K.,Yousuf, Syed Khalid,Singh, Baldev,Tripathi, Anil. K.,Mukherjee, Debaraj
, p. 11023 - 11028 (2014/03/21)
Anomeric gem-diallylation, mono-β-crotylation and mono-β- propargylation of sugar 1,5 and 1,4 lactones have been achieved under Barbier reaction conditions using Zn powder and a catalytic amount of TMSCl as an activator. Ring closing olefin metathesis of the synthesized gem-diallyl derivatives furnished C-spiro cyclopentene glycosides. Finally, the cyclopentene rings were converted into carbohydrate based tricyclic morpholine fused triazole glycoconjugates as potential SGLT2 inhibitors.
CARBOHYDRATE PHOSPHONATE DERIVATIVES AS MODULATORS OF GLYCOSYLATION
-
Paragraph 0109, (2014/09/03)
Compounds of Formula (I) are useful as modulators of glycosylation. Compounds of Formula (I) have the following structure: (I) and the definitions of the other variables are provided herein.
Metal-free oxidative lactonization of carbohydrates using molecular iodine
Fusaro, Maxime B.,Chagnault, Vincent,Josse, Solen,Postel, Denis
, p. 5880 - 5883 (2013/07/25)
We describe herein the oxidative lactonization of fully or partially protected carbohydrates using molecular iodine. Oxidation of aldose hemiacetals is generally carried out by classical procedures, which are rarely chemo or regioselective. We recently re
Design and stereoselective synthesis of a C-aryl furanoside as a conformationally constrained CHIR-090 analogue
Oddo, Alberto,Holl, Ralph
, p. 59 - 64,6 (2020/08/31)
The UDP-3-O-[(R)-3-hydroxymyristoyl]-N-acetylglucosamine deacetylase (LpxC) is a promising target for the development of novel antibiotic substances against multidrug-resistant Gram-negative bacteria. The C-aryl glycoside 3 was designed as conformationally constrained analogue of the potent LpxC-inhibitor CHIR-090. The chiral pool synthesis of 3 started with d-mannose. The C-aryl glycoside 8 was synthesized stereoselectively by nucleophilic attack of 4-iodine-substituted phenyllithium and subsequent reduction with Et 3SiH. The ester 10 was obtained in a one-pot diol cleavage, CrO 3 oxidation, and esterification. A Sonogashira reaction of the aryl iodide 11 led to the alkyne 17 which was transformed with H2NOH into the hydroxamic acid 3.
Highly efficient synthesis of ketoheptoses
Waschke, Daniel,Thimm, Julian,Thiem, Joachim
supporting information; experimental part, p. 3628 - 3631 (2011/09/15)
A reliable, facile, high overall yielding and diastereoselective synthesis of ketoheptoses was developed and applied for preparation of the two most diabetogenic ketoheptoses as well as in a modified version for the synthesis of kamusol.
An oxepinone route to carbohydrate based oxepines
Castro, Steve,Johnson, Courtney S.,Surana, Bikash,Peczuh, Mark W.
experimental part, p. 7921 - 7926 (2009/12/03)
Oxepines are ring expanded analogs of glycals that can be used to prepare septanose carbohydrates. A?route to carbohydrate based oxepines that utilizes oxepinones as a key intermediate has been developed. The oxepinone intermediates were prepared via an a
exo-imino to endo-iminocyclitol rearrangement. A general route to five-membered antiviral azasugars
Moriarty, Robert M.,Mitan, Carmen I.,Branza-Nichita, Norica,Phares, Kenneth R.,Parrish, Damon
, p. 3465 - 3467 (2007/10/03)
A facile synthesis is reported for five-membered iminocyclitols which allows for variation in stereochemistry at all the chiral centers, diverse C1- and N-substitution, and the potential for a three-component combinatorial process. The key step
