58871-10-6Relevant academic research and scientific papers
(2-Benzyloxyphenyl)acetyl (BnPAc): A Participating Relay Protecting Group for Diastereoselective Glycosylation and the Synthesis of 1,2-trans Glycosyl Esters
Weber, Julia,Krauter, Simon,Schwarz, Theresa,Hametner, Christian,Mikula, Hannes
, p. 2265 - 2268 (2018)
The (2-benzyloxyphenyl)acetyl group has been identified as a new protecting group for hydroxyl functions. Various alcohols could be easily protected with high yields, and deprotection was achieved by a relay approach using Pd/H 2 in combination with 1,8-bis(dimethylamino)naphthalene, conditions that are orthogonal to ester groups. The new protecting group is stable in glycosylation reactions demonstrating an effective neighboring group participation leading to the exclusive formation of 1,2-trans glycosides and glycosyl esters.
Carbocyclic Substrate Analogues Reveal Kanosamine Biosynthesis Begins with the α-Anomer of Glucose 6-Phosphate
Vetter, Natasha D.,Jagdhane, Rajendra C.,Richter, Brett J.,Palmer, David R. J.
, p. 2205 - 2211 (2020/09/01)
NtdC is an NAD-dependent dehydrogenase that catalyzes the conversion of glucose 6-phosphate (G6P) to 3-oxo-glucose 6-phosphate (3oG6P), the first step in kanosamine biosynthesis in Bacillus subtilis and other closely-related bacteria. The NtdC-catalyzed r
MOLECULAR PROBES FOR ANALYSIS OF METABOLISM OF GLYCOLYSIS INHIBITORS PRODRUGS AND SYNTHESIS METHODS THEREFORE
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Page/Page column 8; 10, (2020/03/05)
The present invention relates to compounds according to structure (I) whereby one of R1 to R3 is -OCOCD3 and the other two are either hydroxyl or OAc, their synthesis and their use in for the analysis of the metabolism of glycolysis inhibitors.
A Synthetic Bioinspired Carbohydrate Polymer with Mucoadhesive Properties
Balijepalli, Anant S.,Sabatelle, Robert C.,Chen, Mingfu,Suki, Bela,Grinstaff, Mark W.
, p. 704 - 710 (2019/12/11)
Mucoadhesive polymers are of significant interest to the pharmaceutical, medical device, and cosmetic industries. Polysaccharides possessing charged functional groups, such as chitosan, are known for mucoadhesive properties but suffer from poor chemical d
NOVEL ACETATES OF 2-DEOXY MONOSACCHARIDES WITH ANTICANCER ACTIVITY
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Paragraph 0096; 0102; 0103, (2017/04/01)
Novel compounds and methods of using the same to inhibit glycolysis and treat cancer and other diseases are provided herein.
Direct C-H Trifluoromethylation of Glycals by Photoredox Catalysis
Wang, Bang,Xiong, De-Cai,Ye, Xin-Shan
supporting information, p. 5698 - 5701 (2015/12/01)
A mild, efficient, and practical transformation for the direct C-H trifluoromethylation of glycals under visible light has been reported for the first time. This reaction employed fac-Ir3+(ppy)3 as the photocatalyst, Umemoto's reagent as the CF3 source, and a household blue LED or sunlight as the light source. Glycals bearing both electron-withdrawing and -donating protective groups performed this reaction smoothly. This visible light-mediated trifluoromethylation reaction was highlighted by the trifluoromethylation of the biologically important Neu2en moiety.
Improved and large-scale synthesis of different protected d-glucuronals
Mikula, Hannes,Matscheko, Dominik,Schwarz, Markus,Hametner, Christian,Fr?hlich, Johannes
, p. 19 - 23 (2013/04/23)
Although different protected d-glucuronals are used as precursors for the preparation of many compounds, standard procedures and large-scale syntheses are still not described in the literature. In the course of the development of different protected d-glucuronyl donors we developed several versatile methods that can be used for fast and reproducible preparation of large amounts of the key intermediates. d-Glucuronolactone was converted to methyl 3,4-di-O-acetyl-d-glucuronal applying a novel one-pot protocol, which allowed for large-scale synthesis. Introduction of silyl and benzyl groups was achieved using optimized procedures. Furthermore 3,4,6-tri-O-acetyl-d-glucal was used as starting material for an improved preparation of benzyl protected d-glucuronal, which significantly accelerates and simplifies similar methods described in the literature.
Selective deprotection method of N -phenylcarbamoyl group
Akai, Shoji,Tanaka, Rika,Hoshi, Hidekazu,Sato, Ken-Ichi
, p. 8802 - 8808 (2013/09/24)
We report an improved method for the selective deprotection of the N-phenylcarbamoyl group, which yields the corresponding alcohol without affecting other protecting groups. Deprotection was performed using di-tert-butyl dicarbonate and tetra-n-butylammon
Synthesis and preliminary biological evaluation of carba analogues from Neisseria meningitidis A capsular polysaccharide
Gao, Qi,Zaccaria, Cristina,Tontini, Marta,Poletti, Laura,Costantino, Paolo,Lay, Luigi
scheme or table, p. 6673 - 6681 (2012/09/22)
The Gram-negative encapsulated bacterium Neisseria meningitidis type A (MenA) is a major cause of meningitis in developing countries, especially in the sub-Saharan region of Africa. The development and manufacture of an efficient glycoconjugate vaccine ag
Synthesis of pyranoid and furanoid glycals from glycosyl sulfoxides by treatment with organolithium reagents
Gomez, Ana M.,Casillas, Marta,Barrio, Aitor,Gawel, Anna,Lopez, J. Cristobal
experimental part, p. 3933 - 3942 (2009/04/08)
Glycosyl sulfoxides can be conveniently transformed into pyranoid or furanoid glycals by treatment with organolithium reagents. The more likely reaction pathway involves a sulfoxide/metal exchange reaction to generate a glycosyllithium derivative that und
