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Efficient Synthesis of Glycosylated Matijin-Su Derivatives via Ultrasonic Irradiation

Efficient Synthesis of Glycosylated Matijin-Su Derivatives via Ultrasonic Irradiation
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摘要 Matijin-Su (1) is a phenylalanine dipeptide compound with anti-hepatitis B virus (HBV) activity. Previous re- ports suggest that the synthesis of glycosylated Matijin-Su derivatives needs at least 10 steps. To simplify the syn- thetic 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). Matijin-Su (1) is a phenylalanine dipeptide compound with anti-hepatitis B virus (HBV) activity. Previous re- ports suggest that the synthesis of glycosylated Matijin-Su derivatives needs at least 10 steps. To simplify the syn- thetic 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).
出处 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2016年第12期1353-1359,共7页 中国化学(英文版)
关键词 Matijin-Su DIPEPTIDE GLYCOSYLATION ultrasonic irradiation Matijin-Su, dipeptide, glycosylation, ultrasonic irradiation
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