192328-45-3

Basic information

• Product Name: C₃₉H₅₀BrN₃O₁₁Si
• Synonyms: C₃₉H₅₀BrN₃O₁₁Si
• CAS NO: 192328-45-3
• Molecular Weight: 844.829
• Mol File: 192328-45-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: C₃₉H₅₀BrN₃O₁₁Si(CAS DataBase Reference)
• NIST Chemistry Reference: C₃₉H₅₀BrN₃O₁₁Si(192328-45-3)
• EPA Substance Registry System: C₃₉H₅₀BrN₃O₁₁Si(192328-45-3)

Safety Data

• Hazardous Substances Data: 192328-45-3(Hazardous Substances Data)

Upstream product

• 174146-43-1 methyl (2S,3R)-2-amino-3-[(4-fluoro-3-nitro)phenyl]-3-[(tert-butyldimethylsilyl)oxy]propionate 
• 174146-45-3 (2S,3R)-2-[(R)-2-(3-Bromo-4-methoxy-phenyl)-2-tert-butoxycarbonylamino-acetylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester 
• 192328-54-4 (R)-(3-Bromo-4-methoxy-phenyl)-[(R)-2-tert-butoxycarbonylamino-2-(3,5-dihydroxy-4-methoxy-phenyl)-acetylamino]-acetic acid methyl ester 
• 174146-46-4 (2S,3R)-2-[(R)-2-Amino-2-(3-bromo-4-methoxy-phenyl)-acetylamino]-3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester 
• 192328-56-6 (R)-(3-Bromo-4-methoxy-phenyl)-[(R)-2-tert-butoxycarbonylamino-2-(3,5-dihydroxy-4-methoxy-phenyl)-acetylamino]-acetic acid 
• 192328-47-5 methyl (R)-N-(tert-butoxycarbonyl)-2-(3-bromo-4-methoxyphenyl)glycinate 
• 174146-44-2 (R)-(3-Bromo-4-methoxy-phenyl)-tert-butoxycarbonylamino-acetic acid 
• 192328-48-6 (R)-Amino-(3-bromo-4-methoxy-phenyl)-acetic acid methyl ester 
• 174146-42-0 (2S,3R)-2-Amino-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionic acid methyl ester 
• 139517-62-7 (2R)-2-(3-bromo-4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid 
• 223652-65-1 C₃₉H₄₉BrN₄O₁₃Si 
• 174146-48-6 (2S,3R)-2-{(R)-2-(3-Bromo-4-methoxy-phenyl)-2-[(R)-2-tert-butoxycarbonylamino-2-(3,5-dihydroxy-4-methoxy-phenyl)-acetylamino]-acetylamino}-3-(tert-butyl-dimethyl-silanyloxy)-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester 

Relevant articles and documents

Total Synthesis of the Ristocetin Aglycon

The first total synthesis of the ristocetin aglycon is described employing a modular and highly convergent strategy. An effective 12-step (12% overall) synthesis of the ABCD ring system 3 from its amino acid subunits sequentially features an intramolecular aromatic nucleophilic substitution reaction for formation of the diaryl ether and closure of the 16-membered CD ring system (65%), a respectively diastereoselective (3:1, 86%) Suzuki coupling for installation of the AB biaryl linkage on which the atropisomer stereochemistry can be further thermally adjusted, and an effective macrolactamization (51%) for closure of the 12-membered AB ring system. A similarly effective 13-step (14% overall) synthesis of the 14-membered EFG ring system 4 was implemented employing a room-temperature intermolecular SNAr reaction of an o-fluoronitroaromatic for formation of the FG diaryl ether (69%) and a key macrolactamization (92%) with formation of the amide linking residues 1 and 2. The two key fragments 3 and 4 were coupled, and the remaining 16-membered DE ring system was closed via diaryl ether formation to provide the ristocetin tetracyclic ring system (15 steps, 8% overall) enlisting an unusually facile (25 °C, 8 h, DMF, ≥95%) and diastereoselective (≥15:1) aromatic nucleophilic substitution reaction that benefits from substrate preorganization.