76704-35-3Relevant academic research and scientific papers
Synthetic strategies directed towards 5a-carbahexopyranoses and derivatives based on 6-endo-trig radical cyclizations
Gomez, Ana M.,Uriel, Clara,Company, Maria D.,Lopez, J. Cristobal
experimental part, p. 7116 - 7132 (2012/01/06)
Several synthetic strategies directed towards 5a-carbahexopyranoses and based on 6-endo-trig radical cyclization of unsaturated carbohydrate derivatives have been devised. Three elements for regiocontrol to optimize the 6-endo/5-exo ratio have been incorporated, and their efficiencies in directing 6-endo cyclizations have been evaluated. These elements - namely: i) the incorporation of a substituent at C-5 (radical numbering), ii) the use of a vinyl (rather than alkyl) radical, and iii) the inclusion of ring strain in the system - have proved useful when used in combination. The simultaneous presence of two of them also results in 6-endo selectivity. On another topic, the ozonation of the ensuing alkenylstananes to afford diols seems to be based on a tin-oxygen rearrangement, similar to that reported for related vinylsilanes, rather than on remarkable stabilities of tin-containing primary ozonides as we had previously suggested.
Controlled reduction of acarbose: Conformational analysis of acarbose and the resulting saturated products
Bock,Meldal,Refn
, p. 1 - 16 (2007/10/02)
Saturation of the double bond in the non-reducing terminal unit of the tetrasaccharide amylase inhibitor, acarbose (1), with Raney nickel as the catalyst and at pH 8, gave 57% of a ~1:1 mixture of the 5a-carba-gluco (2) and -ido (3) isomers together with
