165875-03-6Relevant academic research and scientific papers
Highly Functionalized Cyclopentanes by Radical Cyclization of Unsaturated Bromolactones. 2. A Facile Synthesis of the First Carbaaldohexofuranoses and Their Conversion to Carbapentofuranoses
Horneman, Anne Marie,Lundt, Inge
, p. 1919 - 1928 (1998)
A novel type of carbasugars, carbaaldohexofuranoses, has been prepared using a 5-exo-trig radical cyclization of C-2 substituted 2,3-unsaturated 7-bromoheptono-1,4-lactones as the key step. During the cyclization step, two stereogenic centers were formed with high stereoselectivity. The lactone moieties of the cyclopentane derivatives were reduced to the alcohols, and the following carbahexofuranoses were synthesized: carba-β-D-mannofuranose, carba-α-L-glucofuranose and 5-amino5-deoxycarba-α-L-glucofuranose. Side chain degradation of the two former compounds gave the carbapentofuranoses: carba-α-L-xylofuranose and carba-β-D-lyxofuranose.
Synthesis of 4a-Carba-d-lyxofuranose Derivatives and Their Evaluation as Inhibitors of GH38 α-Mannosidases
Zaji?ková, Mária,Monco?, Ján,?esták, Sergej,Kóňa, Juraj,Koó?, Miroslav,Bella, Maro?
, p. 1114 - 1124 (2019/01/24)
A synthetic approach to 4a-carba-d-lyxofuranose derivatives starting from d-lyxose is described. The protected 4a-carba-β-d-lyxofuranose was employed as the key intermediate for the synthesis of 4a-carba-d-lyxofuranose derivatives including novel 1-amino-1-deoxy-4a-carba-d-lyxofuranoses. Synthesized 4a-carba-d-lyxofuranoses were evaluated as inhibitors of GH38 α-mannosidases, namely, the Golgi (GMIIb) and lysosomal (LManII) α-mannosidases from Drosophila melanogaster and commercial Jack bean α-mannosidase (JBMan) from Canavalia ensiformis. The biochemical evaluation revealed that only 1-amino-1-deoxy-4a-carba-β-d-lyxofuranose exhibited reasonable inhibitory activity against GMIIb (IC50 = 200 μm). In addition, the results of biological evaluation were discussed by means of molecular modelling.
A new approach to cyclopentitols using CrCl2 mediated domino reaction and ring closing metathesis. the synthesis of 4a-carba-β-d- arabinofuranose and 4a-carba-β-d-lyxofuranose
Mishra, Girija Prasad,Rao, Batchu Venkateswara
experimental part, p. 812 - 817 (2011/08/06)
An efficient method for the syntheses of cyclopentitols from d-ribose is described using Nozaki-Hiyama-Kishi conditions and ring closing metathesis. In this transformation ω-deoxy-ω-iodo ribofuranoside undergoes reductive elimination in the presence of CrCl2 to give the corresponding olefin-aldehyde, which was trapped by a nucleophile under the same conditions to afford the desired diolefinic species. The ring closing metathesis reaction on the diolefinic species with a Grubbs second generation catalyst produced the required carbocycles.
Synthesis of all stereoisomeric carbapentofuranoses
Marschner,Baumgartner,Griengl
, p. 5224 - 5235 (2007/10/02)
All carbocyclic analogs of the pentofuranoses were synthesized starting from norborn-5-en-2-one (1). By using either base- or acid-catalyzed Baeyer- Villiger reaction of 1, the central intermediates 2 and 3 were obtained. The required functionalization of the olefinic double bond was achieved either by cis-hydroxylation in the case of the ribo, lyxo, and α-xylo derivatives or by epoxidation and subsequent opening with aqueous perchloric acid. In the latter case, a pronounced selectivity for opening the epoxy alcohol in the 3- position was found. I an epoxy acetate with both functions on the same side of the ring was used, the eposide was opened in the 2-position by neighboring group participation of the acetate. The requisite side chain degradation was accomplished either by conversion of the ester into an olefin and subsequent dihydroxylation/cleavage reaction or by Curtius rearrangement to the amine and its conversion into an acetate.
