143164-83-4

Upstream product

• 143164-82-3 4,4'-dibenzyloxy-3-<(S)-2-(tert-butoxycarbonylamino)-2-methoxycarbonyl-(R)-1-hydroxyethyl>biphenyl-3'-carbaldehyde 
• 24424-99-5 di-tert-butyl dicarbonate 
• 121124-94-5 2-benzyloxy-5-bromobenzaldehyde 
• 134038-89-4 2-benzyloxy-5-iodobenzaldehyde 
• 121124-96-7 2-(2-(benzyloxy)-5-bromophenyl)-1,3-dioxane 
• 146335-32-2 2-benzyloxy-5-iodobenzoic acid 
• 143164-81-2 4,4'-dibenzyloxy-3'-<(S,S)-N-(tert-butoxycarbonyl)-4-(methoxycarbonyl)-2-oxo-1,3-oxazolidin-5-yl>biphenyl-3-carbaldehyde 
• 146335-34-4 (R)-5-(2-benzyloxy-5-bromo)phenyl-3-tert-butoxycarbonyl-(S)-4-(methoxycarbonyl)oxazolidin-2-thione 
• 143164-80-1 (R)-5-(2-benzyloxy-5-bromo)phenyl-3-tert-butoxycarbonyl-(S)-4-(methoxycarbonyl)oxazolidin-2-one 
• 146335-33-3 (R)-5-(2-benzyloxy-5-bromo)phenyl (S)-4-(methoxycarbonyl)oxazolidin-2-thione 
• 61172-70-1 dimethyl 2-(tert-butoxycarbonylamino)malonate 
• 61172-71-2 2-(tert-butoxycarbonylamino)-3-methoxy-3-oxopropanoic acid 
• 134038-88-3 2-(trimethylsilyl)ethyl α-(dimethoxyphosphoryl)-N-(benzyloxycarbonyl)glycinate 
• 142602-44-6 3-(4,4'-Bis-benzyloxy-3'-formyl-biphenyl-3-yl)-2-tert-butoxycarbonylamino-3-hydroxy-propionic acid methyl ester 

Downstream Products

• 143164-84-5 3-<(S)-2-(benzyloxycarbonylamino)-2-(trimethylsilylethoxycarbonyl)ethyl>-3'-<(S)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)-(R)-1-hydroxyethyl>-4,4'-dibenzyloxybiphenyl 
• 1027532-24-6 (2S,3R)-2-Amino-3-{4,4'-bis-benzyloxy-3'-[(S)-2-benzyloxycarbonylamino-2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-biphenyl-3-yl}-3-hydroxy-propionic acid methyl ester 
• 146388-29-6 (2S,3R)-2-((2S,4R)-5-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-4-hydroxy-pentanoylamino)-3-[4,4'-bis-benzyloxy-3'-((S)-2-benzyloxycarbonylamino-2-pentafluorophenyloxycarbonyl-ethyl)-biphenyl-3-yl]-3-hydroxy-propionic acid methyl ester 
• 146388-31-0 (7R,8S,11S,14S)-5,17-Bis-benzyloxy-14-benzyloxycarbonylamino-11-((R)-3-benzyloxycarbonylamino-2-hydroxy-propyl)-7-hydroxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]henicosa-1⁽¹⁹⁾,2⁽²¹⁾,3,5,16⁽²⁰⁾,17-hexaene-8-carboxylic acid 
• 146388-30-9 (7R,8S,11S,14S)-5,17-Bis-benzyloxy-14-benzyloxycarbonylamino-11-((R)-3-benzyloxycarbonylamino-2-hydroxy-propyl)-7-hydroxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]henicosa-1⁽¹⁹⁾,2⁽²¹⁾,3,5,16⁽²⁰⁾,17-hexaene-8-carboxylic acid methyl ester 
• 871206-25-6 (2S,3R)-2-((2S,4R)-2-Amino-5-benzyloxycarbonylamino-4-hydroxy-pentanoylamino)-3-[4,4'-bis-benzyloxy-3'-((S)-2-benzyloxycarbonylamino-2-pentafluorophenyloxycarbonyl-ethyl)-biphenyl-3-yl]-3-hydroxy-propionic acid methyl ester 
• 143164-86-7 C₆₇H₈₀N₄O₁₅Si 
• 143164-87-8 (2R,3S)-2-((2S,4R)-5-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-4-hydroxy-pentanoylamino)-3-{4,4'-bis-benzyloxy-3'-[(S)-2-benzyloxycarbonylamino-2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-biphenyl-3-yl}-3-hydroxy-propionic acid methyl ester 
• 143164-87-8 (2S,3R)-2-((2S,4R)-5-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-4-hydroxy-pentanoylamino)-3-{4,4'-bis-benzyloxy-3'-[(S)-2-benzyloxycarbonylamino-2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-biphenyl-3-yl}-3-hydroxy-propionic acid methyl ester 

Relevant academic research and scientific papers

The Synthesis of Biphenomycin A

Biphenomycin A, a highly potent antibiotic against Gram-positive, β-lactam-resistant bacteria, which was previously isolated from culture filtrates of Streptomyces griseorubiginosus No. 43708, has now been synthesized.

Total synthesis of the biphenomycins; V. Synthesis of biphenomycin A

The total synthesis of biphenomycin A is described. Two of the five stereogenic centres were formed by enantioselective hydrogenation of the corresponding didehydroamino acids using the rhodium-DIPAMP catalyst and the two stereogenic centres of the α-amin

Diastereoselective formation of (Z)-didehydroamino acid esters

The rearrangement of (E)-didehydroamino acid derivatives to the corresponding Z-derivatives under acid or basic catalysis as well as under the influence of radicals has been investigated. The condensation of N-benzyloxycarbonyl or N-tert-butoxycarbonyl protected alkyl 2-amino-2-(dimethoxyphosphoryl)acetates with aldehydes or ketones in dichloromethane in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene furnishes (Z)-didehydroamino acid ester derivatives diastereoselectively in excellent yields and with high purity.