668-72-4

Basic information

• Product Name: Virginiamycin S₁
• CAS NO: 668-72-4
• Molecular Weight: 823.903
• Mol File: 668-72-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Virginiamycin S₁(CAS DataBase Reference)
• NIST Chemistry Reference: Virginiamycin S₁(668-72-4)
• EPA Substance Registry System: Virginiamycin S₁(668-72-4)

Safety Data

• Hazardous Substances Data: 668-72-4(Hazardous Substances Data)

Upstream product

• 102410-74-2 Fmoc-Thr(H-MePhe-4Kps-Phg-)-D-Abu-Pro-OH*HCl 
• 102410-73-1 Fmoc-Thr(Boc-MePhe-4Kps-Phg-)-D-Abu-Pro-OBu^t 
• 102410-80-0 Pic(3-OH)-Thr(Boc-MePhe-4Kps-Phg-)-D-Abu-Pro-OBu^t 
• 102410-75-3 ((3S,6S,15S,16R,19S,22S)-3-Benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-15-yl)-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 102410-81-1 Pic(3-OH)-Thr(H-MePhe-4Kps-Phg-)-D-Abu-Pro-OH*2HCl 
• 874-24-8 3-hydroxypyridine-2-carboxylic acid 
• 102410-76-4 (3S,6S,15S,16R,19S,22S)-15-Amino-3-benzyl-12-ethyl-4,16-dimethyl-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacosane-2,5,11,14,18,21,24-heptaone 
• 137407-83-1 Carbonic acid 2-((3S,6S,12R,15S,16R,19S)-3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-15-ylcarbamoyl)-pyridin-3-yl ester tert-butyl ester 
• 127092-11-9 3-(2,4-Dinitro-phenoxy)-pyridine-2-carboxylic acid (3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-15-yl)-amide 
• 127106-17-6 Carbonic acid 2-(3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-15-ylcarbamoyl)-pyridin-3-yl ester 2,2,2-trichloro-ethyl ester 
• 127106-16-5 Carbonic acid allyl ester 2-(3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-15-ylcarbamoyl)-pyridin-3-yl ester 
• 117505-35-8 2-({1-[2-(2-[(3-Hydroxy-pyridine-2-carbonyl)-amino]-3-{2-[(4-oxo-piperidine-2-carbonyl)-amino]-2-phenyl-acetoxy}-butyrylamino)-butyryl]-pyrrolidine-2-carbonyl}-methyl-amino)-3-phenyl-propionic acid; compound with trifluoro-acetic acid 

Downstream Products

• 127092-08-4 3-(2-Oxo-2-phenyl-ethoxy)-pyridine-2-carboxylic acid (3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-15-yl)-amide 
• 127092-09-5 C₅₁H₅₅N₇O₁₁ 
• 129412-73-3 virginiamycin S aminoethyloxime 
• 129446-51-1 [3-Benzyl-12-ethyl-15-[(3-hydroxy-pyridine-2-carbonyl)-amino]-4,16-dimethyl-2,5,11,14,18,21-hexaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-(24E)-ylideneaminooxy]-acetic acid 
• 129446-53-3 3-Hydroxy-pyridine-2-carboxylic acid {24-[(E)-2-acetylamino-ethoxyimino]-3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21-hexaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-15-yl}-amide 
• 129446-56-6 {2-[3-Benzyl-12-ethyl-15-[(3-hydroxy-pyridine-2-carbonyl)-amino]-4,16-dimethyl-2,5,11,14,18,21-hexaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-(24E)-ylideneaminooxy]-ethyl}-carbamic acid methyl ester 
• 129446-55-5 3-Hydroxy-pyridine-2-carboxylic acid {3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21-hexaoxo-19-phenyl-24-[(E)-2-(2,2,2-trifluoro-acetylamino)-ethoxyimino]-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-15-yl}-amide 
• 127106-16-5 Carbonic acid allyl ester 2-(3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-15-ylcarbamoyl)-pyridin-3-yl ester 
• 129446-58-8 3-Hydroxy-pyridine-2-carboxylic acid {3-benzyl-24-[(E)-2-(3,3-dimethyl-ureido)-ethoxyimino]-12-ethyl-4,16-dimethyl-2,5,11,14,18,21-hexaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-15-yl}-amide 
• 127106-17-6 Carbonic acid 2-(3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentaaza-tricyclo[20.4.0.0^6,10]hexacos-15-ylcarbamoyl)-pyridin-3-yl ester 2,2,2-trichloro-ethyl ester 
• 127092-10-8 C₄₆H₅₀Cl₃N₇O₁₂ 
• 137407-72-8 C₅₁H₅₇N₇O₁₃ 
• 137407-73-9 C₅₁H₅₈N₈O₁₂ 
• 137407-77-3 C₅₂H₆₅N₇O₁₅ 

Relevant articles and documents

UNIQUE 1'-O-BOC PROTECTION OF VIRGINIAMYCIN S AND RESULTING RESISTANCE AGAINST SODIUM HYDROXIDE

The picolinic hydroxyl in Virginiamycin S1 (VS%1; 1a) can be protected with di-tert-butyloxycarbonate affording the tert-butyloxycarbonyl derivative thus yielding VS1-1'-O-Boc (1b) in a fast and quantitative conversion without concomitant betaine (1c) formation.Once protected however, the lactone bond in 1b can no longer be cleaved under mild alkaline conditions.A possible explanation is given.

A SEARCH FOR PHENOLIC PROTECTION IN VIRGINIAMYCIN S

In order to be able to mask the hydroxyl grouping of the pipecolic acid residue in Virginiamycin during alkaline (NaOH) and acidic (Tfa) break-down procedures and to use peptidic fragments coming thereof for further reconstitution by classical peptide synthesis procedures, we have investigated several candidates for protection/deprotection.Thus the phenacyl derivatives (4 and 5), the allyloxycarbonyl derivative (6), the trichloroethyloxycarbonyl derivatives (8 and 9) and the 2,4-dinitrophenyl derivative (10) have been prepared.Among these none were stable in aqueous basic conditions.The Alloc- (6) the Troc- (8) and Dnp-derivative (10) may have some applications under acidic conditions.