90021-48-0Relevant academic research and scientific papers
The direct synthesis of 6-amino-6-deoxyaldonic acids as monomers for the preparation of polyhydroxylated nylon 6
Chaveriat, Ludovic,Stasik, Imane,Demailly, Gilles,Beaupere, Daniel
, p. 1349 - 1354 (2007/10/03)
6-Azido-6-deoxy-d-galactitol and d-mannitol were obtained quantitatively via the reduction of the corresponding 6-azido-6-deoxy-d-hexono-1,4-lactones, and 6-azido-6-deoxy-d-glucitol was obtained by the reduction of 6-azido-6-deoxyglucose in good yields. The reduction of monoazidodeoxyhexitols by catalytic hydrogenation gave the monoaminohexitol analogues in 95-98% yields. Oxidation of these afforded the corresponding 6-amino-6-deoxy-d-aldonic acids in moderate yields. Alternatively, saponification of 6-azido-6-deoxy-d-hexonolactones gave 6-azido-6-deoxyaldonic acid salts which, after reduction followed by neutralization, led to the expected compounds in 82-88% overall yields.
Acyloxonium ions in the high-yielding synthesis of oxolanes from alditols, hexoses, and hexonolactones catalysed by carboxylic acids in anhydrous hydrogen fluoride
Defaye, Jacques,Gadelle, Andree,Pedersen, Christian
, p. 191 - 202 (2007/10/02)
Treatment of D-glucono-1,5- or D-mannono-1,4-lactone with anhydrous hydrogen fluoride catalysed by formic or acetic acid yields 3,6-anhydro-D-glucono- and -D-mannono-1,4-lactone, respectively.Similarly, D-mannitol is converted into 1,4-anhydro-D-mannitol and subsequently into the 1,4:3,6-dianhydride, whereas D-glucitol forms exclusively the 3,6-anhydride and, on further reaction, 1,4:3,6-dianhydro-D-glucitol.D-Glucose and 2-acetamido-2-deoxy-D-glucose are also converted into the corresponding 3,6-anhydrides by reaction with hydrogen fluoride and formic acid.13C-N.m.r. spectroscopy indicates that the reactions involve intermediate dioxolanyium ions.
