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Synthesis of Novel Guanidinogalactosides
Author(s) -
Yang JinFeng,
Cao LingHua
Publication year - 2009
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200900057
Subject(s) - chemistry , acetylation , isothiocyanate , yield (engineering) , adduct , amine gas treating , nucleophile , proton nmr , elemental analysis , phenyl isothiocyanate , primary (astronomy) , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis , biochemistry , materials science , physics , astronomy , metallurgy , gene
This paper involves the preparation of thioureas, which couple with per‐ O ‐acetylated galactosyl isothiocyanate 1 and 2‐aminobenzothiazole 2 to give incorporating galactosylthiourea derivatives 3. Nucleophilic addition of active primary amine to 3 in the presence of HgCl 2 afforded the per‐ O ‐acetylated guanidinogalactoside 4a‐4d, 5a‐5d, 6a‐6d, 7a‐7d in good yield. These adducts were subjected to deacetylation in MeOH/NaOMe and furnished the corresponding unprotected guanidinogalactosides 8a‐8d, 9a‐9d, 10a‐10d, 11a‐11d. The structures of all newly synthesized compounds were established by IR, 1 H NMR, MS and elemental analysis.
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