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Efficient Synthesis of Glycosylated Matijin‐Su Derivatives via Ultrasonic Irradiation
Author(s) -
Liang Guangping,
Hu Zhanxing,
Yuan Jie,
Liang Guangyi,
Xu Bixue
Publication year - 2016
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.201600468
Subject(s) - chemistry , combinatorial chemistry , dipeptide , hepatitis b virus , phenylalanine , ultrasound , virus , amino acid , biochemistry , virology , biology , physics , acoustics
Matijin‐Su ( 1 ) is a phenylalanine dipeptide compound with anti‐hepatitis B virus (HBV) activity. Previous reports suggest that the synthesis of glycosylated Matijin‐Su derivatives needs at least 10 steps. To simplify the synthetic procedure, we have developed a shorter and more efficient method for the preparation via ultrasound irradiation. Two galactopyranosylated ( 2 ) and two glucopyranosylated ( 3 ) derivatives were synthesized in 6 or 7 steps. The overall yields for the total synthesis of galactopyranosylated derivatives were markedly increased to 39% ( 2a ) or 22% ( 2b ). And the yields for glucopyranosylated derivatives also reached 29% ( 3a ) or 16% ( 3b ).
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