251089-75-5

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 251089-74-4 (8-hydroxymethyl-7-methoxy-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)-carbamic acid benzyl ester 
• 286372-25-6 6-benzyloxycarbonylamino-7-methoxy-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-8-carboxylic acid methyl ester 
• 286372-23-4 2-methoxy-6-methoxycarbonylmethylsulfanyl-3,5-dinitro-benzoic acid methyl ester 
• 286372-24-5 6-amino-7-methoxy-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-8-carboxylic acid methyl ester 
• 251089-58-4 2-fluoro-6-methoxy-3,5-dinitro-benzoic acid methyl ester 
• 178747-79-0 methyl 2-fluoro-6-methoxybenzoate 

Downstream Products

• 286372-63-2 C₃₈H₅₁N₃SO₈C₂H₄O 
• 165337-97-3 (+)-thiazinotrienomycin E 
• 251089-76-6 6-amino-8-benzenesulfonylmethyl-7-hydroxy-4H-benzo[1,4]thiazin-3-one 
• 286372-29-0 8-(1-benzenesulfonyl-4-{6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pent-3-enyl)-6-[(tert-butyl-dimethyl-silanyl)-amino]-7-(tert-butyl-dimethyl-silanyloxy)-4H-benzo[1,4]thiazin-3-one 
• 251089-60-8 (8-benzenesulfonylmethyl-7-methoxy-3-oxo-3,4-dihydro-2H-benzo[1,4]thiazin-6-yl)-carbamic acid benzyl ester 

Relevant academic research and scientific papers

Total synthesis of the ansamycin antibiotic (+)-thiazinotrienomycin E

The first total synthesis of (+)-thiazinotrienomycin E (1), member of a novel class of cytotoxic ansamycin antibiotics, has been achieved. Key features of the synthetic strategy include (a) the efficient construction of sulfone 7 incorporating TBS protection of the aniline, (b) an improved synthesis of allyl chloride (-)-6, the advanced intermediate employed in our trienomycins A and F total syntheses, (c) application of the Kocienski modified Julia protocol to elaborate the E,E,E-triene subunit in a stereo- controlled fashion, (d) an efficient union of sulfone 7 with advanced iodide 62, and (e) Mukaiyama macrolactamization to access the thiazinotrienomycin macrocyclic ring.

Total synthesis of (+)-thiazinotrienomycin E

(equation presented) The first total synthesis of (+)-thiazinotrienomycin E (1), member of a novel class of cytotoxic ansamycin antibiotics, has been achieved. The synthesis features a highly efficient construction of the aromatic fragment 3 incorporating