2946-01-2Relevant academic research and scientific papers
C-3 epimers of sugar amino acids as foldameric building blocks: improved synthesis, useful derivatives, coupling strategies
Nagy, Adrienn,Csordás, Barbara,Zsoldos-Mády, Virág,Pintér, István,Farkas, Viktor,Perczel, András
, p. 223 - 240 (2017/02/05)
To obtain key sugar derivatives for making homooligomeric foldamers or α/β-chimera peptides, economic and multigram scale synthetic methods were to be developed. Though described in the literature, the cost-effective making of both 3-amino-3-deoxy-ribofuranuronic acid (H–tX–OH) and its C-3 epimeric stereoisomer, the 3-amino-3-deoxy-xylofuranuronic acid (H–cX–OH) from d-glucose is described here. The present synthetic route elaborated is (1) appropriate for large-scale synthesis; (2) reagent costs reduced (e.g. by a factor of 400); (3) yields optimized are ~80% or higher for all six consecutive steps concluding –tX– or –cX– and (4) reaction times shortened. Thus, a new synthetic route step-by-step optimized for yield, cost, time and purification is given both for d-xylo and d-ribo-amino-furanuronic acids using sustainable chemistry (e.g. less chromatography with organic solvents; using continuous-flow reactor). Our study encompasses necessary building blocks (e.g. –X–OMe, –X–OiPr, –X–NHMe, Fmoc–X–OH) and key coupling reactions making –Aaa–tX–Aaa– or –Aaa–tX–tX–Aaa– type “inserts”. Completed for both stereoisomers of X, including the newly synthesized Fmoc–cX–OH, producing longer oligomers for drug design and discovery is more of a reality than a wish.
The carbohydrate-sesquiterpene interface. Directed synthetic routes to both (+)- and (-)-fomannosin from D-glucose
Paquette, Leo A.,Peng, Xiaowen,Yang, Jiong,Kang, Ho-Jung
, p. 4548 - 4558 (2008/09/21)
(Chemical Equation Presented) An enantiodivergent strategy for the total chemical synthesis of both naturally occurring (+)-fomannosin (1) and its (-)-antipode (ent-1) from α-D-glucose has been developed and successfully implemented. The key steps in the
Sulfuric acid immobilized on silica: an efficient reusable catalyst for selective hydrolysis of the terminal O-isopropylidene group of sugar derivatives
Rajput, Vishal Kumar,Roy, Bimalendu,Mukhopadhyay, Balaram
, p. 6987 - 6991 (2007/10/03)
Sulfuric acid immobilized on silica proved to be an efficient catalyst for selective hydrolysis of the terminal O-isopropylidene group of sugar derivatives. The method is very simple and economic for large-scale synthesis in which the catalyst is recovered and reused for several runs. Reactions with di-O-isopropylidene derivatives of d-glucose, d-mannose, d-fructose and l-sorbose led to the formation of the corresponding mono-O-isopropylidene derivatives in good to excellent yields.
Selective deprotection of terminal isopropylidene acetals and trityl ethers using HClO4 supported on silica gel
Agarwal, Aditi,Vankar, Yashwant D.
, p. 1661 - 1667 (2007/10/03)
Terminal isopropylidene acetals are selectively cleaved to the corresponding 1,2-diols in good to excellent yields in 6-24 h at room temperature by using the 'HClO4?SiO2' reagent system. Likewise, trityl ethers are readily cleaved to the corresponding alcohols in good to excellent yields within 2-3 h at room temperature. Work-up involves merely filtration of the reagent followed by purification of the crude product.
CBr4-photoirradiation protocol for chemoselective deprotection of acid labile primary hydroxyl protecting groups
Chen, Ming-Yi,Patkar, Laxmikant N.,Jan, Mi-Dan,Lee, Adam Shih-Yuan,Lin, Chun-Cheng
, p. 635 - 639 (2007/10/03)
CBr4-photoirradiation protocol was found to be a mild, highly efficient and selective method for deprotection of isopropylidene, benzylidene, triphenylmethyl and tert-butyldimethylsilyl protecting groups on sugar molecules. The conditions of this reaction can also be used to cleave peptides off from acid-labile resin linkers in solid-phase peptide synthesis.
Synthesis of an enantiomerically pure 2,2,4-trisubstituted cyclobutanone building block by zirconocene-promoted deoxygenative ring contraction of structurally modified 4-vinylfuranosides
Paquette, Leo A.,Kang, Ho-Jung
, p. 1353 - 1358 (2007/10/03)
A route to an enantiopure trisubstituted cyclobutanone has been devised. The pursuit of this building block begins with D-glucose and features a zirconocene-promoted ring contraction.
Synthesis of isoaristeromycin from D-glucose
Singha,Tripathi,Roy,Achari,Mandal
, p. 919 - 924 (2007/10/03)
Isoaristeromycin 1, an analogue of the nucleoside antibiotic aristeromycin, has been synthesized by the application of intermolecular nitrone cycloaddition (INC) reaction on a D-glucose derived substrate.
Yb(OTf)3·H2O: A novel reagent for the chemoselective hydrolysis of isopropylidene acetals
Yadav,Reddy, B. V. Subba,Reddy, K. Srinivasa
, p. 430 - 431 (2007/10/03)
A facile chemoselective hydrolysis of terminal isopropylidene acetals has been achieved using a catalytic amount of Yb(OTf)3·H2O in acetonitrile at ambient temperature.
Oxidation products of arachidonic acid. III. The synthesis of methyl 8R,9R,11R-, 8S,9R,11R-, and 8S,9S,11R-triacetoxyeicosa-5Z,12E,14Z-trienoate
Just, George,Luthe, Corinne
, p. 2286 - 2294 (2007/10/02)
A stereospecific synthesis of the title compounds, starting from readily available glucose derivatives, is described, and methods for differentiating them and the already reported 8R,9S,11R-eicosatrienoate are discussed.
