107819-86-3

Upstream product

• 98433-13-7 7-aminoheptanamide 
• 25508-20-7 N,N'-dibenzyloxycarbonyl-(S)-methyl-isothiourea 
• 929-17-9 7-aminoheptanoic acid 
• 189245-00-9 N,N′-(bis-Cbz-guanidino)heptanoic acid 

Downstream Products

• 189245-01-0 C₂₇H₃₄N₄O₈ 
• 107819-88-5 ω-bis(benzyloxycarbonyl)guanidino-α-(methoxymethyl ester) 
• 189245-01-0 7-[N,N'-bis(benzyloxycarbonyl)-N-(guanidinoheptanoyl)]-α-hydroxyglycine 
• 326854-53-9 C₂₉H₃₆N₄O₉ 
• 189245-02-1 7-[N,N'-bis(benzyloxycarbonyl)guanidino]heptanoyl-(RS)-2-[(R)-sec-phenethoxy]glycine methyl ester 

Relevant academic research and scientific papers

Efficient synthesis of (S)-(-)- and (R)-(+)-enantiomers of 15-deoxyspergualin (15-DSG)

An efficient synthesis of the (S)-(-)- and (R)-(+)-enantiomers of 15-deoxyspergualin (15-DSG) is reported. The synthesis involves preparative HPLC separation and subsequent hydrogenolysis of two diastereoisomers 10a and 10b of fully protected 15-DSG penultimates. Alternatively, diastereomerically pure amide 10b (97% de) was also prepared from acid 8b (97% de), which was obtained via crystallization of a 1:1 diastereomeric mixture of 8a and 8b. Copyright (C) 2000 Elsevier Science Ltd.

Total Synthesis of (+/-)-15-Deoxyspergualin

The synthesis of (+/-)-7-N-butyl>amino>-1-hydroxy-2-oxoethyl>heptanamide trihydrochloride, (+/-)-15-deoxyspergualin, 2b, a potent antitumor and antibiotic spermidine alkaloid, is reported.The synthesis is predicated on the development of the protected spermidine N1,N4-bis(tert-butoxycarbonyl)spermidine (12) and guanidine reagent N,N'-bis(tert-butoxycarbonyl)-S-methylisothiourea (18).The sensitive alkanolamide moiety of (+/-)-15-deoxyspergualin ( C-11 in 2b ) is formed and then protected as its tert-butyldimethylsilyl ether in 21.The reactive ester group of 21 undergoes aminolysis with 12 to from protected deoxyspergualin 22.All of the protecting groups in 22 are removed by trifluoroacetic acid to furnish final product 2b.