N,N,N-Trimethyl-N-(methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranosid-5-yl)ammonium 4-methylbenzenesulfonate sesquihydrate

Abstract

Key indicators: single-crystal X-ray study; T = 200 K; mean (C-C) = 0.005 Å; some non-H atoms missing; disorder in main residue; R factor = 0.051; wR factor = 0.139; data-to-parameter ratio = 15.8.The structure of the title compound, [C 12 H 24 NO 4 ][C 7 H 7 O 3 S]Á-1.5H 2 O, contains alternating layers parallel to (001) of hydrophobic and polar character, stabilized by C-HÁ Á ÁO hydrogen bonding. The furan ring adopts an envelope conformation with the C(OMe) atom as the flap, and the dioxolane ring is twisted about one of the O-C(methine) bonds. A comparison to related compounds is presented. The tosylate-O atoms were disordered over two positions with the major component having a site occupancy factor = 0.566 (12). The structure was refined as a rotary twin with regard to rotation about the c axis with the contribution of the second component being 0.0048 (6). Solvate water molecules are highly disordered and were removed using the SQUEEZE procedure; the unit cell characteristics take into account the presence of the disordered solvent. High-resolution 1 H and 13 C NMR spectroscopic data are also presented. Related literature

Sugar-Based Ionic Liquids: Multifaceted Challenges and Intriguing Potential

“…Among them, d -ribose, one of the main components of RNA that can be obtained on a large-scale by fermentation [ 114 ] of d -glucose, is the most commonly employed building block. Its use for synthesizing ILs was reported in two articles from 2011 to now [ 21 , 115 ]. The same strategy was followed in both papers: The initial selective protection of the secondary hydroxyl groups was followed by transforming the free primary alcohol into a leaving group.…”

“…A very similar strategy was used by Dmochowska et al in 2013 [ 115 ]: Once the protected sugar 165 was obtained [ 116 ], the free hydroxyl group was converted into a mesylate group, and the final product 168 was obtained through an S N 2 reaction with Nme 3 ( Scheme 35 ). This approach presents the above-discussed advantages and limitations.…”

“…Finally, a great number of papers deal with the synthesis and characterization of sugar-derived ionic liquids, like the study of their reduced toxicity, due to the introduction of a sugar unity [ 17 ], the determination of their mutagenic activity [ 32 ], the measurement of their cell viability and cytotoxicity [ 99 ], the investigation of their physicochemical properties [ 34 , 38 , 43 , 65 , 66 , 68 , 82 , 115 ], and their interactions with common solvents [ 46 ].…”

“… Sugar Core Physical State Melting Point (°C) Ref. 167a d -ribose Light brown color solid 157–160 [ 21 ] 167b d -ribose Yellow color solid 124–126 [ 21 ] 167c d -ribose Oily liquid [ 21 ] 167d d -ribose Oily liquid [ 21 ] 167e d -ribose Colorless solid 96–98 [ 21 ] 167f d -ribose Oily liquid [ 21 ] 168 d -ribose Solid 75–78 [ 115 ] 177a …”