14347-78-5Relevant articles and documents
L-(S)-ERYTHRULOSE A NOVEL PRECURSOR TO L-2,3-O-ISOPROPYLIDENE-C3 CHIRONS
Wilde, H. De,Clercq, P. De,Vandewalle, M.,Roeper, H.
, p. 4757 - 4758 (1987)
Starting from L-(S)-erythrulose, now available in larger quantities, the preparation of L-(S)-glyceraldehyde, L-(R)-glycerol and L-(S)-methyl glycerate acetonides, via the protected L-(S)-3,4-O-isopropylideneerythrulose, is described.
Kinetic resolution of (R,S)-1,2-isopropylidene glycerol (solketal) ester derivatives by lipases
MacHado, Antonio C.O.,Da Silva, Angelo A.T.,Borges, Cristiano P.,Simas, Alessandro B.C.,Freire, Denise M.G.
, p. 42 - 46 (2011)
A study on the enantioselective hydrolysis of (R,S)-1,2-isopropylidene glycerol (4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane, solketal) octanoate catalyzed by different lipases was carried out. Among them, Pseudomonas sp. lipase proved to be the most effective. It was shown that the ester bearing the longer octanoyl acyl chain is a more suitable substrate for this lipase compared to the acetate counterpart. By properly combining enzyme load, temperature and reaction time, either the (S)-alcohol or the remaining ester could be obtained in moderate to high selectivities. Ethyl acetate was found to be the best solvent for the kinetic resolutions effected by such lipase but our results show that toluene may prove useful.
Synthesis of (R)- and (S)-isopropylidene glycerol
Pallavicini,Valoti,Villa,Piccolo
, p. 5 - 8 (1994)
The preparation of (R)- and (S)-isopropylidene glycerol 1 of high enantiomeric excess (> 98%) was accomplished through salt formation between their hydrogen phthalates with (S)- and (R)-1-methylbenzylamine [MBA] respectively, selective crystallization of these salts and subsequent regeneration of optically active compounds 1 by saponification. The progress of resolution was followed by HPLC analysis on Chiralcel OJ, after converting the hydrogen phthalates into the corresponding mono methyl esters by diazomethane.
Optically active monoacylglycerols: Synthesis and assessment of purity
Chen, Chao-Yuan,Han, Wei-Bo,Chen, Hui-Jun,Wu, Yikang,Gao, Po
, p. 4311 - 4318 (2013/07/26)
Despite their simple structures, synthesis of 1(or 3)-acyl-sn-glycerols remains a challenge that cannot be ignored because of facile acyl migrations, which not only complicate the synthesis but also make direct GC or HPLC analysis unfeasible. Assessment of the optical purity of monoacylglycerols has, to date, relied almost exclusively on specific rotation data, which are small in value and thus insensitive to impurities. Now, a simple means to "magnify" the small specific rotations has been found, along with practical methods for the measurement of both 1,2-and 1,3-acyl migrations, which offer a convenient and straightforward alternative to Mori's NMR analysis of Mosher esters. With the aid of these methods, a range of conditions for deacetonide removal were examined en route to the synthesis of two natural monoacylglycerols. Refined hydrolysis conditions, along with useful knowledge about the solubility and reactivity of substrates with an ultra long alkyl chain are also presented. Copyright
Asymmetric synthesis of (4S,5S)-2-oxo-4-phenyloxazolidine-5-carboxylic acid using a 1,2-addition of PhMgBr to an N-sulfinimine derived from (R)-glyceraldehyde acetonide and (S)-t-BSA
Babu, K. Chandra,Vysabhattar, Raman,Srinivas,Nigam, Satish,Madhusudhan,Mukkanti
experimental part, p. 2619 - 2624 (2011/01/05)
We report an asymmetric synthesis of (4S,5S)-2-oxo-4-phenyloxazolidine-5- carboxylic acid via stereoselective addition of phenylmagnesium bromide (PhMgBr) to an N-sulfinimine derived from (R)-glyceraldehyde acetonide. (S)- and (R)-Glyceraldehyde acetonides, important chiral synthons in synthetic organic chemistry, are prepared from the corresponding epichlorohydrin using an identical synthetic methodology.