Acetoxy lanostanone
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| Category | Others |
| Catalog number | BBF-04941 |
| CAS | 13553-26-9 |
| Molecular Weight | 484.75 |
| Molecular Formula | C32H52O3 |
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Specification
| Synonyms | Lanost-8-en-24-one, 3β-hydroxy-, acetate (7CI,8CI); (3β)-3-(Acetyloxy)lanost-8-en-24-one; 3β-Acetoxylanost-8-en-24-one |
| IUPAC Name | (3S,5R,10S,13R,14R,17R)-4,4,10,13,14-pentamethyl-17-((R)-6-methyl-5-oxoheptan-2-yl)-2,3,4,5,6,7,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate |
Properties
| Boiling Point | 535.2±50.0°C (Predicted) |
| Density | 1.02±0.1 g/cm3 (Predicted) |
Reference Reading
1. Remote Arylative Substitution of Alkenes Possessing an Acetoxy Group via β-Acetoxy Elimination
Kazuma Muto, Takaaki Kumagai, Fumitoshi Kakiuchi, Takuya Kochi Angew Chem Int Ed Engl. 2021 Nov 8;60(46):24500-24504. doi: 10.1002/anie.202111396. Epub 2021 Oct 13.
Palladium-catalyzed remote arylative substitution was achieved for the reaction of arylboronic acids with alkenes possessing a distant acetoxy group to provide arylation products having an alkene moiety at the remote position. The use of β-acetoxy elimination as a key step in the catalytic cycle allowed for regioselective formation of unstabilized alkenes after chain walking. This reaction was applicable to various arylboronic acids as well as alkene substrates.
2. 3β-Acetoxy-21α-H-hop-22(29)ene, a novel multitargeted phytocompound against SARS-CoV-2: in silico screening
Simna Siddique, R Pradeep Kumar J Biomol Struct Dyn. 2022 Apr 4;1-8. doi: 10.1080/07391102.2022.2058094. Online ahead of print.
The present pandemic disease COVID-19 demands an urgent need for more efficient antiviral drugs against SARS-CoV-2. Computational drug designing and discovery enable us to explore ethnomedicinal plants as a source of various lead molecules that can be used against present and future pathogens. Adiantum latifolium Lam., a common fern, is resistant to pathogens mainly due to the presence of various phytochemicals having antimicrobial properties. In our previous study, 3β-acetoxy-21α-H-hop-22(29)ene, a terpenoid has been characterized from the methanol extract of leaves of A. latifolium. The manuscript evaluates the antiviral potency of the compound against SARS-CoV-2 through molecular docking method. Proteins essential for SARS-CoV-2 multiplication in host cells are the target sites. The study revealed strong binding affinity of the compound for all the ten proteins selected, including seven nonstructural proteins, two structural proteins and one receptor protein, with a binding energy of -4.67 to -8.76 kcal/mol. MDS and MMPBSA analysis of the best ranked complex further confirmed the results. The multitargeted compound can be considered as a natural lead molecule in drug designing against COVID-19, but requires wet-lab experimentation and clinical trials.Communicated by Ramaswamy H. Sarma.
3. Chemoenzymatic enantioselective route to get (+) and (-) 4-acetoxy-azetidin-2-one by lipase-catalysed kinetic resolution and their applications
Giulia Martelli, Martina Cirillo, Valentina Giraldi, Daria Giacomini Bioorg Chem. 2022 Mar;120:105580. doi: 10.1016/j.bioorg.2021.105580. Epub 2021 Dec 31.
4-Acetoxy-azetidin-2-one is an extremely useful intermediate widely applied for the synthesis of several biologically active β-lactam compounds. However, it is available as a racemic mixture that could limit its application in the synthesis of enantiopure products. Herein we evaluated the use of lipases in a kinetic resolution (KR) process to finally obtain 4-acetoxy-zetidin-2-one as separated pure enantiomers. From a preliminary screening on a set of commercial enzymes, Pseudomonas fluorescens emerged as the most suitable lipase that allowed to obtain good conversions and excellent enantiomeric excesses. On the enantiomerically pure 4-acetoxy-azetidin-2-ones some nucleophilic substitutions and N-thio-alkylation reactions were tested in order to evaluate the stereochemical integrity at the C-4 position.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
