Diosgenyl 2-amino-2-deoxy-β-D-galactopyranoside: synthesis, derivatives and antimicrobial activity
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منابع مشابه
Diosgenyl 2-amino-2-deoxy-β-D-galactopyranoside: synthesis, derivatives and antimicrobial activity
The synthesis of diosgenyl 2-amino-2-deoxy-β-D-galactopyranoside is presented for the first time. This synthetic saponin was transformed into its hydrochloride as well as N-acyl, 2-ureido, N-alkyl, and N,N-dialkyl derivatives. Antifungal and antibacterial studies show that some of the obtained compounds are active against Gram-positive bacteria and Candida type fungi.
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Diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside is a synthetic saponin exhibiting attractive pharmacological properties. Different pathways tested by us to obtain this glycoside are summarized here. Moreover, the synthesis of N-alkyl and N,N-dialkyl derivatives of the glucopyranoside is presented. Evaluation of antibacterial and antifungal activities of these derivatives indicates that they have ...
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Efficient syntheses of three [C]methyl 2-[N]amino-2-deoxy-D-glucopyranoside derivatives are described. Amination of the D-glucal with (saltmen)Mn(N) proceeded with 11:1 stereoselectivity favoring the gluco configuration; subsequent methylation of the [N]lactol using [C]iodomethane and silver(I) oxide afforded the doubly labeled glucoside in high yield. This compound served as the common precurs...
متن کاملMethyl 2-acetamido-2-deoxy-β-D-glucopyranoside dihydrate and methyl 2-formamido-2-deoxy-β-D-glucopyranoside.
Methyl 2-acetamido-2-deoxy-β-D-glucopyranoside (β-GlcNAcOCH(3)), (I), crystallizes from water as a dihydrate, C(9)H(17)NO(6)·H(2)O, containing two independent molecules [denoted (IA) and (IB)] in the asymmetric unit, whereas the crystal structure of methyl 2-formamido-2-deoxy-β-D-glucopyranoside (β-GlcNFmOCH(3)), (II), C(8)H(15)NO(6), also obtained from water, is devoid of solvent water molecul...
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ژورنال
عنوان ژورنال: Beilstein Journal of Organic Chemistry
سال: 2017
ISSN: 1860-5397
DOI: 10.3762/bjoc.13.227