173532-18-8Relevant articles and documents
Structure-property relationships of ribose based ionic liquids
Jopp, Stefan,Komabayashi, Mirai,Stiller, Tanja
, (2021)
The authors of this work have successfully synthesized a broad choice of new ribose based ionic liquids, using several varying protecting groups (methyl, ethyl, allyl and benzyl) at the various positions of the carbohydrate, as well as different quarternised N-heterocycles and different anions. These consistent variations of the carbohydrate based ionic liquids (CHILs) enabled an extensive structure-property relationship study of thermal properties, allowing the authors to prove existing trends and to find a correlation between the decomposition temperature and the structure of the CHILs.
Dipyrrolidinomethylaminophosphoric acid triamide (DPMPA) as an activator for the samarium diiodide-mediated reduction of alkyl and aryl halides
McDonald, Chriss E.,Ramsey, Jeremy R.,Sampsell, David G.,Anderson, Laura A.,Krebs, Jordan E.,Smith, Samantha N.
, p. 2947 - 2953 (2013/04/23)
The use of the conjugate base of dipyrrolidinomethylaminophosphoric triamide (DPMPA-) as an activator of samarium diiodide is reported. This phosphoramidate has been shown to be a very potent ligand, allowing for the efficient, low-temperature reduction of alkyl and aryl chlorides. Reductive cyclizations of haloalkenylnaphthalenes are also reported.
Synthesis of C-(D-glycopyranosyl)ethylamines and C-(D-glycofuranosyl)methylamines as potential glycosidase inhibitors
Abdel-Rahman, Adel A.-H.,El Ashry, El Sayed H.,Schmidt, Richard R.
, p. 106 - 116 (2007/10/03)
The C-glucosyl aldehyde, 2-C-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)ethanal was prepared from the C-glucopyranosyl propene precursor by ozonolysis. Reductive amination of the C-glucosyl aldehyde and subsequent deprotection gave 1-anilino-2-C-(α-D-glucopyranosyl)ethane. The E and Z isomers of the oxime derivative, 1-C-(α-D-arabinofuranosyl)methanal oxime were prepared by treating their aldehyde precursor with hydroxylamine. Acetylation of the oxime, followed by catalytic hydrogenation and deprotection, gave the corresponding 1-C-(α-D-arabinofuranosyl)methylamine. Reductive amination of ethyl 2,3-O-isopropylidene-α-D-lyxo-pentodialdo-1,4-furanoside using aniline gave ethyl 5-anilino-5-deoxy-D-lyxo-furanoside. Inhibition studies with these compounds on β-D-glucosidase from sweet almond, using o-nitrophenyl D-glucopyranoside as substrate, were carried out. Copyright (C) 1999 Elsevier Science Ltd.
2,3-Aziridino-2,3-dideoxy-D-ribono-γ-lactone 5-Phosphonate: Stereocontrolled Synthesis from D-Lyxose and Unusual Aziridine Ring Opening
Dauban, Philippe,Dodd, Robert H.
, p. 4277 - 4284 (2007/10/03)
The synthesis of (1R,4S,5S)-N-(benzyloxycarbonyl)-4-[(diethoxyphosphinyl)methyl]-3-oxa-6- azabicyclo[3.1.0]hexan-2-one (23), a new member of the 2,3-aziridino γ-lactone family of compounds, was achieved in 15 steps from D-lyxose. Like all aziridino γ-lactones known so far, 23 reacted with a soft nucleophile (ethanethiol) to give exclusively the product of aziridine ring opening at C-2 (24). On the other hand, hard nucleophiles (alcohols) did not react directly with the aziridine ring of 23 but appeared to promote intramolecular attack of the aziridine ring at C-3 by the C-5 phosphonate group, resulting, after hydrolytic workup, in formation of the 2-amino-3-hydroxy-D-ribono-1,4-lactone derivatives 25 and 26, instead of the expected 2-amino-3-alkoxy-D-xylono-1,4-lactone derivatives.
