173775-54-7

Basic information

• Product Name: D-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-3-nitro-
• CAS NO: 173775-54-7
• Molecular Formula: C14H17FN2O6
• Molecular Weight: 328.297
• Mol File: 173775-54-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: D-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-3-nitro-(CAS DataBase Reference)
• NIST Chemistry Reference: D-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-3-nitro-(173775-54-7)
• EPA Substance Registry System: D-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-3-nitro-(173775-54-7)

Safety Data

• Hazardous Substances Data: 173775-54-7(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 459-57-4 4-fluorobenzaldehyde 
• 178217-05-5 (R)-2-(Benzhydrylidene-amino)-3-(4-fluoro-3-nitro-phenyl)-propionic acid tert-butyl ester 
• 42564-51-2 4-fluoro-3-nitrobenzaldehyde 
• 20274-69-5 (4-fluoro-3-nitrophenyl)methanol 
• 188624-30-8 (R)-N-trifluoroacetyl-4-fluoro-3-nitrophenylalanine methyl ester 
• 188624-24-0 (RS)-N-trifluoroacetyl-4-fluoro-3-nitrophenylalanine methyl ester 
• 20367-99-1 ethyl 2-(acetylamino)-2-(ethoxycarbonyl)-3-(4'-fluoro-3'-nitrophenyl)propanoate 
• 169825-20-1 (3R,6S)-2,5-dimethoxy-6-isopropyl-3-(4-fluoro-3-nitrophenyl)-3,6-dihydro-1,4-pyrazine 
• 169825-21-2 D-(4-fluoro-3-nitrophenyl)glycine methyl ester 
• 15017-52-4 4-(bromomethyl)-1-fluoro-2-nitrobenzene 
• 331731-26-1 (R)-N-(tert-butoxycarbonyl)-4-fluoro-3-nitrophenylalanine methyl ester 

Downstream Products

• 178217-07-7 (R)-[(S)-2-[(R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-2-(3,5-dimethoxy-phenyl)-acetylamino]-(3-hydroxy-4-methoxy-phenyl)-acetic acid methyl ester 
• 178744-34-8 C₄₅H₄₉F₂N₇O₁₆ 
• 178744-44-0 (S)-2-[(R)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-propionic acid 
• 173775-56-9 [(8R,11S,14R)-8-Hydroxymethyl-11-(3-isopropoxy-phenyl)-19-nitro-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaen-14-yl]-carbamic acid tert-butyl ester 
• 173775-58-1 2-(3-Fluoro-4-nitro-phenyl)-N-[(8R,11S,14R)-8-hydroxymethyl-11-(3-hydroxy-phenyl)-19-nitro-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaen-14-yl]-acetamide 
• 173775-57-0 (8R,11S,14R)-14-Amino-8-hydroxymethyl-11-(3-hydroxy-phenyl)-19-nitro-2-oxa-9,12-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-10,13-dione 
• 331731-45-4 [1-({{3-[5-(2-benzyloxy-1-tert-butoxycarbonylamino-ethyl)-2-methoxy-phenoxy]-5-methoxy-phenyl}-[1-(3,5-dihydroxy-4-methoxy-phenyl)-2-hydroxy-ethylcarbamoyl]-methyl}-carbamoyl)-2-(4-fluoro-3-nitro-phenyl)-ethyl]-carbamic acid tert-butyl ester 
• 331731-41-0 {3-[5-(2-benzyloxy-1-tert-butoxycarbonylamino-ethyl)-2-methoxy-phenoxy]-5-methoxy-phenyl}-[2-tert-butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-acetic acid 
• 331731-34-1 {2-benzyloxy-1-[3-(3-{1-[2-tert-butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-2-hydroxy-ethyl}-5-methoxy-phenoxy)-4-methoxy-phenyl]-ethyl}-carbamic acid tert-butyl ester 
• 312305-13-8 [1-[1-({[4-allyloxy-3-bromo-5-(tert-butyl-dimethyl-silanyloxy)-phenyl]-methylcarbamoyl-methyl}-carbamoyl)-ethylcarbamoyl]-2-(4-fluoro-3-nitro-phenyl)-ethyl]-carbamic acid tert-butyl ester 
• 203311-03-9 methyl N-[N-(tert-butyloxycarbonyl)-L-(3,4-dihydroxyphenylalanyl)]-D-4-fluoro-3-nitrophenylalaninate 

Relevant articles and documents

First and second generation-total synthesis of the teicoplanin aglycon

Full details of studies leading to the total synthesis of the teicoplanin aglycon are provided. Key elements of the first generation approach (26 steps from constituent amino acids, 1% overall) include the coupling of an EFG tripeptide precursor to the common vancomycin/teicoplanin ABCD ring system and sequential DE macrocyclization of the 16-membered ring with formation of the diaryl ether via a phenoxide nucleophilic aromatic substitution of an o-fluoronitroaromatic (80%, 3:1 atropisomer diastereoselection) followed by 14-membered FG ring closure by macrolactamization (66%). Subsequent studies have provided a second generation total synthesis which is shorter, more convergent, and highly diastereoselective (22 steps, 2% overall). This was accomplished by altering the order of ring closures such that FG macrolactamization (95%) preceded coupling of the EFG tripeptide to the ABCD ring system and subsequent DE ring closure. Notably, DE macrocyclization via diaryl ether formation on substrate 57, the key intermediate in the latter approach incorporating the intact FG ring system, occurred with exceptional diastereoselection for formation of the natural atropisomer (> 10:1, 76%) without problematic C23 epimerization provided the basicity of the reaction is minimized.

Synthetic studies towards glycopeptide antibiotics: Synthesis of the 16-membered cyclic tripeptide (DOEG ring) system of teicoplanin

The synthesis of the 16-membered cyclic DOEG ring system of teicoplanin, which forms the binding pocked for the carboxylate region of terminal D-Ala-D-Ala of the bacterial cell wall via macroetherification of linear tripeptide 20 is described.