A short synthesis of d-[1-(14) C]-serine of high enantiomeric purity.
نویسندگان
چکیده
Herein, we report a short, three-step synthesis of d-[1-(14) C]-serine (4) in high enantiomeric purity. Starting from [(14) C]-KCN and 2-(benzyloxy)acetaldehyde, Strecker reaction using (R)-1-phenylethylamine as the chiral auxiliary gave two diastereomeric aminonitriles 1 and 2 in the ratio of 4:3, which were conveniently separated and purified chromatographically. Following hydrolysis and subsequent hydrogenolysis, the purified major diastereomer 1, was smoothly converted to d-[1-(14) C]-serine (4) in an enantiomeric excess of >99%, thus circumventing time intensive chiral HPLC enantiomeric resolution.
منابع مشابه
EFFECT OF FABRICATION PARAMETERS ON SYNTHESIS OF Ti2AlC AND Ti3AlC2MAX PHASES BY MASHS
Mechanically Activated Self-propagating High temperature Synthesis (MASHS) is the method which is used to promote self-propagating synthesis by increasing activity of reactants and increase the purity of products. In this study Ti 2 AlC and Ti3AlC2 max phases were synthesized by using mechanically activated self-propagating high temperature synthesis (MASHS) and samples reactivity and phase str...
متن کاملA new approach for the synthesis of 3,4-dihydropyrano[c]chromenes and biscoumarins using {[2,2’-BPyH][C(CN)3]2} as a bifunctional nanostructured ionic liquid catalyst
[2,2'-Bipyridine]-1,1'-diium tricyanomethanide {[2,2'-BPyH][C(CN)3]2} as a bifunctional nanostructured ionic liquid catalyst (0.5 mol%) was used for the synthesis of 3,4-dihydropyrano[c]chromenes (14 examples) under solvent-free condition at room temperature in high yield (82-91%) and short reaction time. In addition, the described ionic liquid catalyst was also applied for the synthesis of bis...
متن کاملDetermination of the enantiomeric purity of mevalonolactone via NMR using a chiral lanthanide shift reagent.
Simple methods for determining the enantiomeric purity of mevalonolactone and linalool by NMR using the chiral shift reagent Eu(hfc)3 are reported. These methods are more reliable than polarimetry and require only a few milligrams of sample to detect as little as 2% of the minor enantiomer. The accuracy of these methods is limited primarily by spectral resolution for samples of high enantiomeri...
متن کاملFumarase-Catalyzed Synthesis of t-threo-Chloromalic Acid and lts Conversion to 2-Deoxy-D-ribose and D-erythro-Sphingosine
These enzyrnes are indisputably valuable but have certain disadvantages, among which is often imperfect enantioselectivity. The standards in enantioselective synthesis are now very high: for most applications, an enantiomeric excess (ee) in an enantioselective step of less than 90% is essentially useless, and values of ee >99% are very desirable.a It is often difficult to achieve broad substrat...
متن کاملRational design and synthesis of homochiral azole antifungal agents*
The first synthesis of both enantiomers of the antifungal drug bifonazole (1a) and related imidazole compounds 1i and 5b,c is described, starting from enantiomerically pure or enriched amines 6a–d. Construction of the imidazole ring on amines 6a–d was performed in a straightforward manner affording the final compounds in good overall yield and with very high enantiomeric purity, as determined b...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Journal of labelled compounds & radiopharmaceuticals
دوره 58 4 شماره
صفحات -
تاریخ انتشار 2015