1256121-14-8

Basic information

• Product Name: C₁₆H₁₆F₅NO₄
• Synonyms: C₁₆H₁₆F₅NO₄
• CAS NO: 1256121-14-8
• Molecular Weight: 381.299
• Mol File: 1256121-14-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₁₆H₁₆F₅NO₄(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₆H₁₆F₅NO₄(1256121-14-8)
• EPA Substance Registry System: C₁₆H₁₆F₅NO₄(1256121-14-8)

Safety Data

• Hazardous Substances Data: 1256121-14-8(Hazardous Substances Data)

Upstream product

• 146553-06-2 tert-butyl {(S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl}carbamate 
• 79069-50-4 Boc-Ala-H 
• 14533-84-7 pentafluorophenyl trifloroacetate 
• 142723-69-1 [L-(trans)]-4-[(t-butoxycarbonyl)amino]-2-pentenoic acid 
• 15761-38-3 L-N-Boc-Ala 

Relevant articles and documents

Total synthesis and antimalarial activity of symplostatin 4

The first total synthesis of symplostatin 4, a marine cyanobacterium- derived natural product, is described. Notable features of the route include the efficient preparation of three key fragments and final assembly to the natural product via sequential imide and amide couplings. Symplostatin 4 was also demonstrated to possess significant antimalarial activity (ED50 of 74 nM against Plasmodium falciparum, strain 3D7).

Total synthesis, stereochemical assignment, and antimalarial activity of gallinamide A

The total synthesis and stereochemical assignment of gallinamideA, an antimalarial depsipeptide of cyanobacterial origin, is described. Synthesis of the four possible N-terminal diastereoisomers of gallinamideA (including the natural product symplostatin4) was achieved using a divergent strategy from a common imide fragment. The natural product and corresponding diastereoisomers were synthesized in 30-33% overall yield in a longest linear sequence of 8 steps. Comparative NMR spectroscopic studies of the four synthetic diastereoisomers with the isolated natural product demonstrated that gallinamideA possesses a dimethylated L-isoleucyl residue at the N-terminus. As such, we have shown that gallinamideA is structurally and stereochemically identical to symplostatin4. GallinamideA and its N-terminal diastereoisomers were also shown to possess significant antimalarial activity with IC 50 values in the nanomolar range against the 3D7 strain of Plasmodium falciparum. Naturally active: The total synthesis of gallinamideA, a cyanobacterium-derived depsipeptide, is described. Four N-terminal diastereoisomers of gallinamide A were prepared by using two key fragments (see scheme). Spectroscopic comparison to the isolated natural product enabled the absolute configuration of the N,N-dimethylated isoleucyl residue to be determined as 25S, 26S. GallinamideA (and its diastereoisomers) were also shown to possess potent antimalarial activity. Copyright