116087-59-3Relevant academic research and scientific papers
Regioselective Synthesis of Difluorinated C-Furanosides Involving a Debenzylative Cycloetherification
Delbrouck, Julien A.,Bochatay, Valentin N.,Tikad, Abdellatif,Vincent, Stéphane P.
supporting information, p. 5562 - 5566 (2019/08/01)
A highly regioselective synthesis of valuable gem-difluorinated C-furanosides from unprotected aldoses via a debenzylative cycloetherification (DBCE) reaction induced by diethylaminosulfur trifluoride is descibed. The scope and limitations of this DBCE reaction are described using a series of commercially available pentoses and hexoses to afford, without selective protection/deprotection sequences, the corresponding gem-difluorinated C-furanosides in moderate to good yields.
Synthesis of sialic acid derivatives based on chiral substrate-controlled stereoselective aldol reactions using pyruvic acid oxabicyclo[2.2.2]octyl orthoester
Norimura, Yusuke,Yamamoto, Daisuke,Makino, Kazuishi
supporting information, p. 640 - 648 (2017/01/25)
The synthesis of sialic acids and their analogs was accomplished based on substrate-controlled asymmetric aldol reactions between sterically complicated aldehydes easily prepared from commercially available carbohydrates and a novel pyruvic acid oxabicyclo[2.2.2]octyl orthoester. Systematic aldol reaction studies using chiral aldehydes revealed that α,β,γ-benzyloxy-substituted aldehydes with an α,β-anti relative configuration preferentially provided the Felkin products with the 4,5-anti configuration with high diastereoselectivity. The relative β,γ-configuration in α,β,γ-benzyloxy-substituted aldehydes with an α,β-syn arrangement exerted a secondary effect on the diastereoselectivity of the stereogenic center formed in aldol reactions, and α,β-syn-β,γ-anti benzyloxyaldehyde exhibited superior diastereoselectivity to α,β-syn-β,γ-syn benzyloxyaldehyde to yield the Felkin products.
Condensation of D-mannosaldehyde derivatives with ethyl diazoacetate. An easy and stereoselective chain elongation methodology for carbohydrates: Application to new syntheses for KDO and 2-deoxy-β-KDO
Lopez-Herrera, Fidel J.,Sarabia-Garcia, Francisco
, p. 3325 - 3346 (2007/10/03)
(3R and 3S) β-Hydroxy-α-diazocarbonyl compounds 4 (100%, 3:2), 9 (35%, 100:0), 14 (74%, 7:2) and 18 (100%, 100:0), prepared from 2,3,4,5,6-penta-O-acetyl-(3), penta-O-benzyl- (8), 2,3:5,6-di-O-isopropylidene-4-O-(tert-butyldimethylsilyl)- (13), and 2,3:5,6-di-O-isopropylidene-4-O-acetyl-D-mannosaldehyde (17), respectively, were acetylated, and the resulting β-3cetoxy-α-diazocarbonyl compounds treated with rhodium diacetate to give the corresponding α-enol esters, 6 (100%). 11 (35%), 16 (100%) and 20 (100%) which are potentially α-keto eaters. Molecular mechanics calculations were used in order to justify the stereoselectivity observed in the initial addition process: The problematic removal of the projecting groups from the α-enol esters is discussed. Finally, hydrazinolysis of the a-enol acetates (to quench the labile resulting α-keto ester as the corresponding and less reactive hydrazines), mild oxidation to the corresponding α-diazoesters, deprotection, and final oxidation of the diazo group with m-chloroperbenzoic acid, gave KDO in good yield. Intermediate products were used in the completely stereoselective synthesis of 2-deoxy-β-KDO, a potent inhibitor for CMP-KDO synthetase.
SHORT SYNTHESIS OF C-ARYL-GLUCOPYRANOSIDES OF THE PAPULACANDIN TYPE
Schmidt, Richard R.,Frick, Wendelin
, p. 7163 - 7170 (2007/10/02)
The aryllithium species 5a-A and 5b-A generated via bromine/lithium exchange reaction, afforded with the per-O-benzylated D-glucose 6 the adducts 9a,b; subsequent oxidation furnished the corresponding ketones 10a,b.Compound 10a was also obtained from 5a-A
