Gusperimus hydrochloride, Deoxyspergualin hydrochloride, BMY-42215-1, BMS-181173, NSC-356894, NKT-01, DSG, Spanidin

合成路线:2) By an acid catalyzed condensation of 7-guanidinoheptanamide (IX) with an equivalent amount of glyoxylspermidine (X) in the presence of glutaric acid at 60 C for 8 h.Purification of the reaction mixture gives DSG in 39% yield.

参考文献标题:(-)-15-Deoxyspergualin,process for the preparation thereof,and intermediate of the same
文献作者:Umezawa,H.; Takeuchi,T.; Kondo,S.(Microbial Chemistry Research Foundation)
参考来源:US 4525299


合成路线:1) By a stepwise conversion of spergualin to DSG in the following sequence:a) Protecting the primary and secondary amines of spergualin with N-(benzyloxycarbonyloxy)suc cinimide to form the N,N'-benzyloxycarbonyl derivative (I);b) protecting the 11-hydroxy group with 3,4-dihydro-2H-pyran to the 11-O tetrahydropyranyl derivative (II);c) converting the 1,5-hydroxy function of (II) to a 1,5-mesylate (III);d) halogenation of (III) with sodium iodide,followed by catalytic hydrogenation,to give 15-deoxy-1-O-tetrahydropyranylspergualin (IV);e) hydrolysis of (IV) with p-toluenesulfonic acid in water to yield 1,5-deoxyspergualin.The overall yield of DSG is 1.8%,based on the amount of spergualin used.

参考文献标题:(-)-15-Deoxyspergualin,a process for the preparation of the same,an intermediate of the same,and its use as medicament
文献作者:Kondo,S.; Takeuchi,T.; Umezawa,H.(Microbial Chemistry Research Foundation)
参考来源:EP 0094632


合成路线:2) By an acid catalyzed condensation of 7-guanidinoheptanamide (IX) with an equivalent amount of glyoxylspermidine (X) in the presence of glutaric acid at 60 C for 8 h.Purification of the reaction mixture gives DSG in 39% yield.

参考文献标题:N-[4-(3-Aminopropyl)aminobutyl]-2,2-dihydroxyethanamide and process for its synthesis
文献作者:Ikeda,D.; Nakamura,T.; Fujii,A.; Umezawa,H.; Kondo,S.; Iinuma,H.; Takeuchi,T.(Microbial Chemistry Research Foundation)
参考来源:DE 3217693; GB 2100253


合成路线:2) By an acid catalyzed condensation of 7-guanidinoheptanamide (IX) with an equivalent amount of glyoxylspermidine (X) in the presence of glutaric acid at 60 C for 8 h.Purification of the reaction mixture gives DSG in 39% yield.

参考文献标题:Method for producing glyoxylspermidine and the use thereof for the production of 15-deoxy spergualin-related cpds.
文献作者:Takeuchi,T.; Fujii,A.; Nakamura,T.; Umeda,Y.; Moriguchi,M.; Umezawa,H.(Nippon Kayaku Co.,Ltd.; Takara Shuzo Co.,Ltd.)
参考来源:DE 3506330; US 4603015


合成路线:2) By an acid catalyzed condensation of 7-guanidinoheptanamide (IX) with an equivalent amount of glyoxylspermidine (X) in the presence of glutaric acid at 60 C for 8 h.Purification of the reaction mixture gives DSG in 39% yield.

参考文献标题:(S)-7-Guanidino-3-hydroxyheptanamide and its synthesis method
文献作者:Takeuchi,T.; Umezawa,H.; Kondo,S.; Nakamura,T.; Iinuma,H.; Ikeda,T.; Fujii,A.(Microbial Chemistry Research Foundation)
参考来源:JP 1982188562


合成路线:2) By an acid catalyzed condensation of 7-guanidinoheptanamide (IX) with an equivalent amount of glyoxylspermidine (X) in the presence of glutaric acid at 60 C for 8 h.Purification of the reaction mixture gives DSG in 39% yield.

参考文献标题:Purification method of spergualin or its derivs.
文献作者:Suzuki,M.; Nishizawa,R.; Takei,M.; Yoshida,M.(Nippon Kayaku Co.,Ltd.)
参考来源:JP 1984029652