316828-42-9

Basic information

• Product Name: C₅₀H₄₅N₅O₈
• Synonyms: C₅₀H₄₅N₅O₈
• CAS NO: 316828-42-9
• Molecular Weight: 843.936
• Mol File: 316828-42-9.mol

Chemical Properties

• CAS DataBase Reference: C₅₀H₄₅N₅O₈(CAS DataBase Reference)
• NIST Chemistry Reference: C₅₀H₄₅N₅O₈(316828-42-9)
• EPA Substance Registry System: C₅₀H₄₅N₅O₈(316828-42-9)

Safety Data

• Hazardous Substances Data: 316828-42-9(Hazardous Substances Data)

Upstream product

• 118-92-3 anthranilic acid 
• 422319-55-9 (2S,9R,9aS)-9-Hydroxy-2-isobutyl-9-[(R)-2-methoxycarbonyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-ethyl]-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester 
• 316828-36-1 N_in-L-benzyloxycarbonylleucyl-N_a-2,2,2-trichloroethoxycarbonyl-2-iodo-D-tryptophan methyl ester 
• 316828-38-3 (2S,9R)-9-Hydroxy-2-isobutyl-9a-methoxy-9-[(R)-2-methoxycarbonyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-ethyl]-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester 
• 316828-34-9 methyl (αR,2S)-2,3-dihydro-2-(2-methylpropyl)-3-oxo-1-[(phenylmethoxy)carbonyl]-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1H-imidazo(1,2-a)indole-9-propanoate 
• 316828-39-4 C₃₂H₃₂N₄O₆ 
• 316828-32-7 N_in-L-benzyloxycarbonylleucyl-N_a-2,2,2-trichloroethoxycarbonyl-D-tryptophan methyl ester 
• 316828-41-8 C₂₈H₂₈Cl₃N₃O₇ 
• 316828-59-8 3-(2,3-dihydro-1H-indol-3-yl)-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionic acid methyl ester 
• 14907-27-8 (R)-(+)-tryptophan methyl ester hydrochloride 
• 2018-66-8 Z-Leu-OH 
• 316828-40-7 C₅₀H₄₇N₅O₉ 
• 316828-30-5 N_α-2,2,2-trichloroethoxycarbonyl-D-tryptophan methyl ester 

Downstream Products

• 316828-43-0 N-19-benzyloxycarbonyl-fumiquinazoline I 

Relevant articles and documents

Total synthesis of (-)-fumiquinazolines A, B, C, E, H, and I. Approaches to the synthesis of fiscalin A

The first syntheses of (-)-fumiquinazolines A, B, and I, which proceed in 14 steps from protected tryptophan, anthranilic acid, leucine, and alanine in 7% overall yield, are described. Tricycle 30 was formed by a palladium-catalyzed cyclization. Oxidation of 30a with saccharine-derived oxaziridine 21 for fumiquinazolines A and B and oxidation of 30b with dimethyldioxirane for fumiquinazoline I selectively formed the appropriate imidazoindolone stereoisomers. Application of the Ganesan-Mazurkiewicz cyclization completed the syntheses. Efficient 14-step syntheses of (-)-fumiquinazolines C (7) and E (3) and a 15-step synthesis of (-)-fumiquinazoline H (8) using FmocNHCH(CH2SePh)CO2H as a dehydroalanine precursor that spontaneously eliminated benzeneselenol without oxidation under the cyclization conditions are also reported. Model 86 for fiscalins A with the H and OH anti to each other has been prepared, but the procedure that worked for the model failed with the fully functionalized side chain.

Total syntheses of (-)-fumiquinazolines A, B, and I.

[structure] The first total syntheses of (-)-fumiquinazolines A, B, and I have been accomplished efficiently using the Pd-catalyzed cyclization of an iodoindole carbamate to construct the imidazoindolone moiety and the dehydrative cyclization of a diamide