866336-41-6Relevant academic research and scientific papers
Formation and selective rupture of 1,4-anhydroseptanoses
Vannam, Raghu,Pote, Aditya R.,Peczuh, Mark W.
supporting information, p. 418 - 425 (2017/01/03)
Formation 1,4-anhydroseptanose sugars via intramolecular attack of a benzyl ether oxygen onto an anomeric electrophile is reported. The regioselectivity of the cyclization was confirmed by NMR spectroscopy and an X-ray structure of a glucose-derived 1,4-anhydroseptanose. The transformation is relatively general and was applied to septanoses derived from glucose, mannose, xylose, and galactose. Regioselective opening of the 1,4-anhydro species to give septanose glycosides in preference to furanoses is also demonstrated.
Synthesis of C-septanosides from pyranoses via vinyl addition and electrophilic cyclization
Vannam, Raghu,Peczuh, Mark W.
supporting information, p. 4122 - 4125 (2013/09/12)
A two-step synthesis of C-septanosides from pyranoses is reported. Vinyl addition to tetra-O-benzyl d-glucose, d-galactose, and d-mannose gave the corresponding allylic alcohols. Electrophilic cyclization followed by treatment with iodine gave iodomethyl C-septanosides suitable for substitution reactions. The cyclizations were diastereoselective, giving cis-1,2 configured C-septanosides. Selectivity is rationalized through a model for electrophilic additions that invokes the conformation of the allylic system. This new approach should be generally applicable to the synthesis of a variety of C-septanosides.
Glycosylations with a septanosyl fluoride donor lacking a C2 protecting group
Saha, Jaideep,Peczuh, Mark W.
supporting information, p. 5667 - 5670 (2012/11/07)
Septanosyl fluorides, prepared from protected pyranoses, were used as donors in glycosylation reactions. The fluorides were synthesized by the addition of vinyl Grignard to the pyranoses followed by ozonolysis and then DAST-mediated fluorination. Activation in the presence of nucleophiles then provided the product glycosides. High α-stereoselectivity was observed for glycosylations using a donor that had a free C2 hydroxyl group; a model where the hydroxyl group participates to guide the stereochemical outcome is proposed.
On the synthesis of vinyl and phenyl C-furanosides by stereospecific debenzylative cycloetherification
Cribiù, Riccardo,Eszter Borbas,Cumpstey, Ian
experimental part, p. 2022 - 2031 (2009/07/18)
Open-chain benzyl-ether-protected polyols in which one of the alcohols is either allylic or benzylic are synthesised by addition of organometallic vinyl or phenyl reagents to benzyl-ether-protected carbohydrate hemiacetals. The diastereoselectivity of add
Stereospecific debenzylative cycloetherification of carbohydrate-derived allylic alcohols, ethers and esters to form vinyl C-furanosides
Cribiu, Riccardo,Cumpstey, Ian
, p. 1246 - 1248 (2008/12/21)
Benzyl ether protected polyhydroxylated alkene compounds containing allylic alcohol, ether or ester functionality undergo a stereospecific cyclisation reaction upon treatment with TFA-acetonitrile-toluene with inversion of configuration at the allylic position and loss of a benzyl ether to give tetrahydrofurans. The Royal Society of Chemistry.
Studies on the synthesis of valienamine and 1-epi-valienamine starting from d-glucose or l-sorbose
Cumpstey, Ian,Gehrke, Sebastian,Erfan, Sayeh,Cribiu, Riccardo
, p. 1675 - 1692 (2008/12/21)
Two synthetic routes to a carbocyclic precursor to valienamine are reported, starting from either d-glucose or l-sorbose and using ring-closing metathesis as a key step. A low-yielding synthesis of 1-epi-valienamine is reported. Results from an abortive third possible route to valienamine based on an early introduction of nitrogen are discussed.
