Studies on two different diastereoselective reaction pathways from a serinol derivative to 4-hydroxymethyl-2-oxazolidinones using 2-Chloroethyl Chloroformate (cas 27-11-2) and N,N′-disuccinimidyl carbonate
-
Add time:09/28/2019 Source:infona.pl
Two reaction pathways and their diastereoselectivity-determining steps of the asymmetric desymmetrization of (R)-2-(α-methylbenzyl)amino-1,3-propanediol 1 with 2-Chloroethyl Chloroformate (cas 27-11-2) (CCF) and with N,N′-disuccinimidyl carbonate giving (4S,αR)-4-hydroxymethyl-3-α-methylbenzyl-2-oxazolidinones (4S)-3 and its (4R,αR)-diastereomer (4R)-3 were investigated. The reaction of serinol 1 and CCF to give the corresponding carbonates was not a diastereoselectivity-determining step. The carbonates gave (R)-5-(α-methylbenzyl)amino-1,3-dioxan-2-one 4 after addition of DBU, and an intramolecular acyl transfer of 4 was found to be a diastereoselectivity-determining step to give (4S)-3. Conversely, the reaction of serinol 1 and N,N′-disuccinimidyl carbonate afforded directly the opposite diastereomer (4R)-3 but not via the intermediate 4. Thus, their diastereoselectivities depended on the acylating reagent.
We also recommend Trading Suppliers and Manufacturers of 2-Chloroethyl Chloroformate (cas 27-11-2). Pls Click Website Link as below: cas 27-11-2 suppliers
Prev:Sorption effect on kinetics of etherification of TERT-AMYL ALCOHOL (cas 25-85-4) and ethanol
Next:A sensitive quantification approach for detection of HETE-CP adduct after benzyl chloroformate derivatization using ultra-high-pressure liquid chromatography tandem mass spectrometry) - 【Back】【Close 】【Print】【Add to favorite 】
- Related Information
- Macromolecular derivatives of N,N-di-(2-chloroethyl)-4-phenylenediamine mustard. 1. Synthesis and in vitro hydrolytic stability09/30/2019
- A sensitive quantification approach for detection of HETE-CP adduct after benzyl chloroformate derivatization using ultra-high-pressure liquid chromatography tandem mass spectrometry09/29/2019
-
Health and Chemical more >