147438-27-5

Basic information

• Product Name: 2-Piperidinecarboxylicacid,1-[2-oxo-2-[(2R,3R,6S)-tetrahydro-2-hydroxy-6-[(2S,3E,5E,7E,9S,11R,13R,14R,15E,17R,19E,21R)-14-hydroxy-22-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-2,13-dimethoxy-3,9,11,15,17,21-hexamethyl-12,18-dioxo-3,5,7,15,19-docosapentaen-1-yl]-3-methyl-2H-pyran-2-yl]acetyl]-,(2E,4R,6E,8R)-
• Synonyms: 2-Piperidinecarboxylicacid, 1-[oxo[(2R,3R,6S)-tetrahydro-2-hydroxy-6-[(2S,3E,5E,7E,9S,11R,13R,14R,15E,17R,19E,21R)-14-hydroxy-22-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-2,13-dimethoxy-3,9,11,15,17,21-hexamethyl-12,18-dioxo-3,5,7,15,19-docosapentaenyl]-3-methyl-2H-pyran-2-yl]acetyl]-(9CI); 2-Piperidinecarboxylic acid,1-[oxo[tetrahydro-2-hydroxy-6-[14-hydroxy-22-(4-hydroxy-3-methoxycyclohexyl)-2,13-dimethoxy-3,9,11,15,17,21-hexamethyl-12,18-dioxo-3,5,7,15,19-docosapentaenyl]-3-methyl-2H-pyran-2-yl]acetyl]-,[2R-[2a,2(S*),3a,6b[2S*,3E,5E,7E,9S*,11R*,13R*,14R*,15E,17R*,19E,21R*,22(1S*,3R*,4R*)]]]-;Secorapamycin A
• CAS NO: 147438-27-5
• Molecular Formula: C51H79 N O13
• Molecular Weight: 914.187
• Mol File: 147438-27-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-Piperidinecarboxylicacid,1-[2-oxo-2-[(2R,3R,6S)-tetrahydro-2-hydroxy-6-[(2S,3E,5E,7E,9S,11R,13R,14R,15E,17R,19E,21R)-14-hydroxy-22-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-2,13-dimethoxy-3,9,11,15,17,21-hexamethyl-12,18-dioxo-3,5,7,15,19-docosapentaen-1-yl]-3-methyl-2H-pyran-2-yl]acetyl]-,(2E,4R,6E,8R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Piperidinecarboxylicacid,1-[2-oxo-2-[(2R,3R,6S)-tetrahydro-2-hydroxy-6-[(2S,3E,5E,7E,9S,11R,13R,14R,15E,17R,19E,21R)-14-hydroxy-22-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-2,13-dimethoxy-3,9,11,15,17,21-hexamethyl-12,18-dioxo-3,5,7,15,19-docosapentaen-1-yl]-3-methyl-2H-pyran-2-yl]acetyl]-,(2E,4R,6E,8R)-(147438-27-5)
• EPA Substance Registry System: 2-Piperidinecarboxylicacid,1-[2-oxo-2-[(2R,3R,6S)-tetrahydro-2-hydroxy-6-[(2S,3E,5E,7E,9S,11R,13R,14R,15E,17R,19E,21R)-14-hydroxy-22-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-2,13-dimethoxy-3,9,11,15,17,21-hexamethyl-12,18-dioxo-3,5,7,15,19-docosapentaen-1-yl]-3-methyl-2H-pyran-2-yl]acetyl]-,(2E,4R,6E,8R)-(147438-27-5)

Safety Data

• Hazardous Substances Data: 147438-27-5(Hazardous Substances Data)

Usage

General Description

2-Piperidinecarboxylic acid, 1-[2-oxo-2-[(2R,3R,6S)-tetrahydro-2-hydroxy-6-[(2S,3E,5E,7E,9S,11R,13R,14R,15E,17R,19E,21R)-14-hydroxy-22-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-2,13-dimethoxy-3,9,11,15,17,21-hexamethyl-12,18-dioxo-3,5,7,15,19-docosapentaen-1-yl]-3-methyl-2H-pyran-2-yl]acetyl]-, (2E,4R,6E,8R)- is a complex chemical compound with a long and intricate chemical structure. It contains various functional groups such as carboxylic acid, ketone, hydroxyl, and methyl groups. The compound is a derivative of piperidinecarboxylic acid and contains a pyran-2-yl acetyl group. The compound's stereochemistry is indicated by the presence of (2R,3R,6S), (2S,3E,5E,7E,9S,11R,13R,14R,15E,17R,19E,21R), and (2E,4R,6E,8R) configurations. The molecule is highly complex and potentially biologically active due to the presence of multiple functional groups and stereochemical features.

Upstream product

• 53123-88-9 sirolimus 

Downstream Products

• 155257-20-8 (S)-1-{2-[(2R,3R,6S)-6-((3E,5E,7E)-(2S,9S,11R)-2,13-Dimethoxy-3,9,11-trimethyl-12-oxo-trideca-3,5,7-trienyl)-2-hydroxy-3-methyl-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid (2-cyclohex-1-enyl-ethyl)-amide 
• 155257-16-2 C₅₉H₉₂N₂O₁₂ 

Relevant articles and documents

An intramolecular ionic hydrogen bond stabilizes a cis amide bond rotamer of a ring-opened rapamycin-degradation product

Rapamycin (1), a macrolide immunosuppressant, undergoes degradation into ring-opened acid products 2 and 3 under physiologically relevant conditions. The unsaturated product (3) was isolated and studied in this work. Unlike 1, which has its amide primarily in a trans conformation in solution, 3 has both cis and trans conformations in approximately a 1:1 ratio in dimethyl sulfoxide (DMSO). The amount of cis rotamer was increased dramatically in the presence of an organic base such as triethylamine. The detailed NMR results indicate that the cis rotamer is stabilized through an intramolecular ionic hydrogen bond of the carboxylate anion with the tertiary alcohol as part of a nine-membered ring system. This hydrogen bond was characterized further in organic media and the trans-cis rotamer equilibria were used to estimate the relative bond strengths in several solvents. The additional stabilization arising from this ionic hydrogen bond in the cis rotamer was determined to be 1.4 kcal mol-1 in DMSO-d6, 2.0 kcal mol-1 in CD3CN and 1.1 kcal mol-1 in CD3OD. Copyright

Degradation of rapamycin: Synthesis of a rapamycin derived fragment containing the tricarbonyl and triene sectors

A degradation of rapamycin involving retro-Michael and retro-aldol steps retrieves the entire C1-C27 subunit.