1211774-37-6

Basic information

• Product Name: C₆₉H₁₀₈Cl₃N₁₁O₂₃S
• CAS NO: 1211774-37-6
• Molecular Weight: 1598.1
• Mol File: 1211774-37-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₆₉H₁₀₈Cl₃N₁₁O₂₃S(CAS DataBase Reference)
• NIST Chemistry Reference: C₆₉H₁₀₈Cl₃N₁₁O₂₃S(1211774-37-6)
• EPA Substance Registry System: C₆₉H₁₀₈Cl₃N₁₁O₂₃S(1211774-37-6)

Safety Data

• Hazardous Substances Data: 1211774-37-6(Hazardous Substances Data)

Upstream product

• 1211774-29-6 C₁₈H₃₀Cl₃N₅O₈S 
• 1146698-92-1 tert-butyl 5-O-[5-tert-butoxycarbonylamino-5-deoxy-2,3-O-(3-pentylidene)-β-D-ribo-pentofuranosyl]-6-deoxy-6-(3-isocyanopropyl)amino-2,3-O-isopropylidene-1-(uracil-1-yl)-β-D-glycelo-L-talo-heptofuranuronate 
• 20781-20-8 2,4-Dimethoxybenzylamine 
• 1119-16-0 isocaproic aldehyde 
• 590-86-3 isovaleraldehyde 

Relevant articles and documents

Mechanistic analysis of muraymycin analogues: A guide to the design of MraY inhibitors

The systematic structure-activity relationship (SAR) of the muraymycins (MRYs) using an Ugi four-component reaction (U4CR) was investigated. The impact of the lipophilic substituent on antibacterial activity was significant, and the analogues 8 and 9 having a lipophilic side chain exhibited good activity against a range of Gram-positive bacterial pathogens, including MRSA and VRE. Further investigation of compounds 8 and 9 revealed these analogues to be selective inhibitors of the MraY transferase and nontoxic to HepG2 cells. The SAR of the accessory urea-peptide moiety indicated that it could be simplified. Our SAR study of the MRYs suggests a probable mechanism for inhibition of the MraY, where the inner moiety of the urea-dipeptide motif interacts with the carbohydrate recognition domain in the cytoplasmic loop 5. The predicted binding model would provide further direction toward the design of potent MraY inhibitors. This study has set the stage for the generation of novel antibacterial "lead" compounds based on MRYs. (Figure presented)

Total synthesis of (-)-muraymycin D2 and its epimer

Chemical Equetion Presentation Full details of the first total synthesis of (-)-muraymycin (MRY) D2 and its epimer, the antibacterial nucleoside natural product, are described. Key strategic elements of the approach include the preparation of the urea dipeptide moiety found in the muraymycins containing an L-epi-capreomycidine via a nitrene C-H insertion of the sulfamate 10 and the fully protected muraymycin skeleton at a late stage by an Ugi four-component reaction. Thus, the nitrene C-H insertion of the sulfamate 10 with 10 mol % of Rh2(esp)2 catalyst gave the cyclic sulfamates 11a and 11b in 47% yield (11a:11b = 1:2.0). Construction of the cyclic guanidine skeleton was effected through the HgBr2-promoted cyclization of 42 followed by desulfonylation upon acetolysis of the oxathiazinane ring to give 43 in good yield. The amine obtained by selective removal of the Cbz group of the alcohol 44 was reacted with MeSC(=O)-L-Val-O-t-Bu (38) to provide 45, which was oxidized to the carboxylic acid 46. Reaction of 46, isonitrile 51, isovaleraldehyde, and 2,4-dimethoxybenzylamine furnished the desired Ugi products, the final deprotection of which successfully afforded (-)-MRY D2 and epi-MRY D2 (53) after HPLC separation of the diastereomers. This approach would afford ready access to a range of analogues simply by altering each component.