Synthesis method of new 1,2,3-triazole lincomycin analogs

• Main Authors: XU FENGBO, REN XINXIA, ZHOU XIUXIU, LIU TINGTING, WANG WENHU
• Format: Patent
• Language: Chinese; English
• Published: 05.06.2013
• Subjects: CHEMISTRY; CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION ORPROCESSING OF GOODS; DERIVATIVES THEREOF; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; METALLURGY; NUCLEIC ACIDS; NUCLEOSIDES; NUCLEOTIDES; ORGANIC CHEMISTRY; SUGARS; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS; TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINSTCLIMATE CHANGE

The invention relates to new 1,2,3-triazole lincomycin analogs and a synthesis method thereof, belonging to the field of organic synthesis. The method comprises the following steps: azidating amino group on lincosamide II, protecting hydroxy group with benzyl bromide to obtain a compound IV, removing azido group with triphenylphosphine to obtain aminated saccharide V, amidating the aminated saccharide V to obtain VI, carrying out [3+2] cycloaddition reaction on the compound VI and different azides to obtain benzylated 1,2,3-triazole lincomycin analogs VIII, and debenzylating to obtain a series of now 1,2,3-triazole lincomycin analogs IX with potential antibacterial activity, wherein the lincosamide II can be prepared by carrying out alkalization and hydrazinolysis on lincomycin hydrochloride.