81203-58-9

Upstream product

• 51757-14-3 rifamycin S-O₂₁,O₂₃ acetonide 
• 76123-33-6 C₄₄H₅₇NO₁₄ 
• 76123-20-1 (2Z,4E)-(R)-6-[(4R,5S,6S)-6-((1S,2S,3S,4R)-2-Acetoxy-4-methoxy-1,3-dimethyl-6-methylsulfanyl-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-2-methyl-hepta-2,4-dienoic acid methyl ester 
• 76123-32-5 (2Z,4E)-(R)-6-[(4R,5S,6S)-6-((1S,2S,3S,4R)-2-Acetoxy-6-chloro-4-methoxy-1,3-dimethyl-6-methylsulfanyl-hexyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-2-methyl-hepta-2,4-dienoic acid methyl ester 
• 6998-60-3 rifamycin SV 
• 13929-35-6 Rifamycin B 
• 14487-05-9 rifamycin O 
• 14897-39-3 monosodium rifamycin SV 
• 6998-60-3 C₃₇H₄₇NO₁₂ 

Downstream Products

• 4075-42-7 3-Pyrrolidinomethyl-rifamycin SV 
• 4267-47-4 3-Piperidinomethyl-rifamycin SV 
• 4075-44-9 3-<4-Methyl-piperazinomethyl>-rifamycin SV 
• 17555-08-7 3-(4-methyl-piperazin-1-yl)-rifamycin 
• 4075-49-4 3--rifamycin SV 
• 4075-47-2 3-<4-Methyl-piperidinomethyl>-rifamycin SV 
• 4233-83-4 3--rifamycin SV 
• 33397-70-5 3-(4-phenyl-piperidin-1-yl)-rifamycin 
• 37839-20-6 3-(4-benzyl-piperidin-1-yl)-rifamycin 
• 33024-15-6 3-(4-cyclohexyl-piperidin-1-yl)-rifamycin 
• 31692-65-6 8-Acetylrifamycin S 
• 52608-24-9 3-(2-methoxy-anilino)-O¹,O⁴-didehydro-rifamycin 
• 19306-01-5 3-cyclohexylamino-O¹,O⁴-didehydro-rifamycin 
• 37839-24-0 3-(4-dicyclohexylmethyl-piperidin-1-yl)-rifamycin 

Relevant academic research and scientific papers

Highly Efficient Synthesis of a Staphylococcus aureus Targeting Payload to Enable the First Antibody–Antibiotic Conjugate

A practical synthesis of the complex payload for an anti-Staphylococcus aureus THIOMABTM antibody–antibiotic conjugate (TAC) is described. The route takes advantage of a delicate oxidative condensation, achieved using a semi-continuous flow procedure. It allows for the generation of kilogram quantities of a key intermediate to enable a mild nucleophilic aromatic substitution to the tertiary amine free drug. The linker component is introduced as a benzylic chloride, which allows formation of the quaternary ammonium salt linker-drug. This chemical process surmounts numerous synthetic challenges and navigates deeply colored and unstable compounds to support clinical studies to counter S. aureus bacterial infections.

Deciphering the late steps of rifamycin biosynthesis

Rifamycin-derived drugs, including rifampin, rifabutin, rifapentine, and rifaximin, have long been used as first-line therapies for the treatment of tuberculosis and other deadly infections. However, the late steps leading to the biosynthesis of the industrially important rifamycin SV and B remain largely unknown. Here, we characterize a network of reactions underlying the biosynthesis of rifamycin SV, S, L, O, and B. The two-subunit transketolase Rif15 and the cytochrome P450 enzyme Rif16 are found to mediate, respectively, a unique C-O bond formation in rifamycin L and an atypical P450 ester-to-ether transformation from rifamycin L to B. Both reactions showcase interesting chemistries for these two widespread and well-studied enzyme families.

Process Investigations on the One-Pot Synthesis of Rifamycin S Avoiding Chlorinated Solvents

The facile synthesis of rifamycin S from rifamycin B, a member of the ansamycin family of antibiotics, via the oxidation of rifamycin B was developed. Currently on an industrial scale, this oxidation is performed using harsh pH conditions and chlorinated solvents. With the development of a suitable buffer/methanol system, a similar yield and space-time-yield in comparison to the current process can be obtained renouncing chlorinated solvents. Employment of methanol as a reaction medium in this process is crucial for attaining high yields under mild reaction conditions. With this method a space-time-yield of 189 g L-1 h-1 of rifamycin S was achieved in one step.

Process for preparing rifamycin S by hydrolysis of rifamycin O

A process for preparing rifamycin S from rifamycin O. Rifamycin O is dissolved in a mixture of an organic solvent and an alcohol at room temperature. The rifamycin O is then hydrolyzed with a mineral acid and the thus obtained rifamycin S is purified by crystallization.