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High-Throughput Five Minute Microwave Accelerated Glycosylation Approach to the Synthesis of Nucleoside Libraries

All Rights Reserved. High-Throughput Five Minute Microwave Accelerated Glycosylation Approach to the Synthesis of Nucleoside Libraries. Bookser, Brett C.; Raffaele, Nicholas B. (Metabasis Therapeutics, Incorporated, La Jolla, CA 92037, USA). Journal of Organic Chemistry, 72(1), 173-179 (English) 2007 American Chemical Society. CODEN: JOCEAH. ISSN: 0022-3263. DOCUMENT TYPE: Journal CA Section: 33 (Carbohydrates) The Vorbruggen glycosylation reaction was adapted into a one-step 5 min/130 °C microwave assisted reaction.Some commonly used reagents like 68-94-0 is used in this experiment. Triethanolamine in acetonitrile contg. 2% water was detd. to be optimal for the neutralization of trimethylsilyl triflate allowing for direct MPLC purifn. of the reaction mixt. When coupled with a NH3/methanol deprotection reaction, a high-throughput method of nucleoside library synthesis was enabled. The method was demonstrated by examg. the ribosylation of 48 nitrogen contg. heteroarom. bases that included 25 purines, four pyrazolopyrimidines, two 8-azapurines, one 2-azapurine, two imidazopyridines, two benzimidazoles, three imidazoles, three 1,2,4-triazoles, two pyrimidines, two 3-deazapyrimidines, one quinazolinedione, and one alloxazine. Of these, 32 yielded single regioisomer products, and six resulted in separable mixts. Seven examples provided inseparable regioisomer mixts. of -two to three compds. (16 nucleosides), and three examples failed to yield products. For the 45 single isomers isolated, the av. two-step overall yield ± SD was 26 ± 16%, and the av. purity ± SD was 95 ± 6%. A total of 58 different nucleosides were prepd. of which 15 had not previously been accessed directly from glycosylation/deprotection of a readily available base. .