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Study on the alkylation reaction of guanine and N ‐acetylguanine and the synthesis of 1′‐ C alkylated carba‐DHPG analogues
Author(s) -
Liu YuGang,
Fei ChangPei,
Chan TakHang
Publication year - 1994
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.19940120112
Subject(s) - chemistry , alkylation , yield (engineering) , isopropyl , catalysis , regioselectivity , solvent , medicinal chemistry , alkyl , base (topology) , bromide , coupling reaction , guanine , organic chemistry , mathematical analysis , nucleotide , biochemistry , materials science , mathematics , metallurgy , gene
The alkylation reaction of guanine and N ‐acetylguanine with model compounds such as isopropyl bromide or 4‐heptyl tosylate were studied. The reaction conditions such as temperature, solvent, base, and catalyst were examined for their effects on the reaction rate, and the yield and regioselectivity of the coupling reaction. The highest yield was obtained by using DMSO as the solvent. The reaction proceeded in a homogenous manner to give higher yield of 9‐ N and 7‐ N substituted product in a mole ratio of 1:1. The ratio could be raised to 2:1 if dibenzo‐18‐crown‐6 was used as a catalyst. Using the above procedure, three carba‐DHPG analogues bearing different 1′‐C alkyl side chains were synthesized.