120104-34-9Relevant academic research and scientific papers
Formation of septanoses from hexopyranosides via 5,6-exo-glycals
Jackowski, Olivier,Chretien, Francoise,Didierjean, Claude,Chapleur, Yves
, p. 93 - 103 (2012/08/08)
Methyl d-hexo-5-ulosides are obtained in high yield by dihydroxylation of 5,6-exo-glucal compounds. The bicyclic structure (1,6-anhydropyrano-5-ulose) of the products is adopted in solution and in solid state in a 4C 1 conformation.
Intramolecular 1,8-hydrogen-atom transfer reactions in (1→4)-O- disaccharide systems: Conformational and stereochemical requirements
Francisco, Cosme G.,Herrera, Antonio J.,Kennedy, Alan R.,Martin, Angeles,Melian, Daniel,Perez-Martin, Ines,Quintanal, Luis M.,Suarez, Ernesto
supporting information; experimental part, p. 10369 - 10381 (2009/10/16)
The stereochemical and conformational factors controlling the intramolecular hydrogen-atom transfer (HAT) reaction between the two pyranose units in a (1→4)-O-disaccharide when promoted by a primary 6-O-yl radical are studied. Models with α-D-Glcp-(1→4)-β-D-Glcp, α-L-Rhamp-(1→ 4)-α-D-Galp or α-D-Manp-(1→4)-β- L-Gulp skeletons led exclusively to the abstraction of the hydrogen from H-C-5' and the formation, through a nine-membered transition state, of a 1,3,5-trioxocane ring system in a stable boat-chair conformation. Notwithstanding, derivatives of α-L-Rhamp-(1→4)-α-D-Glcp or α-D-Manp-(1→4)-α-D-Galp exclusively abstract the hydrogen from H-C-1' through a seven-membered transition state and, therefore, lead to an interglycosidic spiro ortho ester.
Syntheses of 6-Deoxyhex-5-enopyranosides from 6-Bromo-6-deoxy- or 6-O-p-Tolylsulfonylhexopyranosides by the Use of DBU in DMSO
Sato, Ken-ichi,Kubo, Noriyuki,Takada, Ritsuko,Sakuma, Shogo
, p. 1156 - 1165 (2007/10/02)
Various kinds of nonbranched and methyl-branched 6-deoxyhex-5-enopyranoside derivatives were prepared from 6-bromo-6-deoxy or 6-O-p-tolylsulfonylhexopyranoside in a one-pot procedure by a successive treatment with iodide anion and 1,8-diazabicyclou
