128947-19-3

Usage

Uses

Used in Pharmaceutical Industry:
N-Propionyl-(2S)-bornane-10,2-sultam is used as an intermediate in the synthesis of drugs for its potential applications in central nervous system activity. Its unique structure allows for the development of novel therapeutic agents that can target specific neurological disorders or conditions.
Used in Agrochemical Industry:
N-Propionyl-(2S)-bornane-10,2-sultam is utilized as an intermediate in the production of agrochemicals, contributing to the development of effective and targeted pest control solutions.
Used in Organic Synthesis:
N-Propionyl-(2S)-bornane-10,2-sultam is used as a chiral building block in organic synthesis, enabling the creation of enantiomerically pure compounds with specific biological activities. Its chiral center plays a crucial role in the development of asymmetric synthesis methods, which are essential for producing optically active compounds with desired properties.
Used in Asymmetric Synthesis:
N-Propionyl-(2S)-bornane-10,2-sultam is employed in asymmetric synthesis as a key component, facilitating the production of enantiomerically enriched compounds. This is particularly important in the pharmaceutical industry, where the stereochemistry of a drug can significantly impact its efficacy and safety.

Upstream product

• 79-03-8 propionyl chloride 
• 108448-77-7 (+)-camphorsultam 

Downstream Products

• 108448-77-7 (+)-camphorsultam 
• 404890-70-6 Thiocarbonic acid O-[(1R,2S)-1-((2S,6R)-6-allyl-tetrahydro-pyran-2-ylmethyl)-3-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-methyl-3-oxo-propyl] ester O-phenyl ester 
• 943154-64-1 (2S)-N-{(2R)-2-[(dibenzylamino)methyl]propanoyl}camphorsultam 
• 947696-83-5 C₃₁H₄₉NO₆SSi 
• 947696-82-4 C₂₅H₃₅NO₆S 
• 899798-75-5 (2S,3R,4R,5S)-7-Benzyloxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2,4-dimethyl-heptan-1-one 
• 899798-74-4 (2S,3R,4S,5S)-7-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-1-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-3-hydroxy-2,4-dimethyl-heptan-1-one 

Relevant academic research and scientific papers

Optimization of globomycin analogs as novel gram-negative antibiotics

Discovery of novel classes of Gram-negative antibiotics with activity against multi-drug resistant infections is a critical unmet need. As an essential member of the lipoprotein biosynthetic pathway, lipoprotein signal peptidase II (LspA) is an attractive target for antibacterial drug discovery, with the natural product inhibitor globomycin offering a modestly-active starting point. Informed by structure-based design, the globomycin depsipeptide was optimized to improve activity against E. coli. Backbone modifications, together with adjustment of physicochemical properties, afforded potent compounds with good in vivo pharmacokinetic profiles. Optimized compounds such as 51 (E. coli MIC 3.1 μM) and 61 (E. coli MIC 0.78 μM) demonstrate broad spectrum activity against gram-negative pathogens and may provide opportunities for future antibiotic discovery.

CYCLIC PEPTIDE ANTIBIOTICS

Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of lipoprotein signal peptidase II (LspA), a key protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.

CYCLIC PEPTIDE ANTIBIOTICS

Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of lipoprotein signal peptidase II (LspA), a key protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.

Stereoselective synthesis of the C3-C12 subunit of laulimalide

A stereoselective synthesis of the C3-C12 subunit of the tumor growth inhibitors laulimalide is disclosed. The key steps of the synthesis include asymmetric alkylation using Oppolzer's protocol and an asymmetric hetero-Diels-Alder reaction using Jacobsen'

Stereoselective synthesis of stable isotope-labeled L-α-amino acids: Electrophilic amination of oppolzer's acyl sultams in the synthesis of L-[15N]alanine, L-[15N]valine, L-[15N]leucine, L-[15N]phenylalanine and

Using 1-chloro-1-[15N]nitrosocyclohexane, we have prepared five L-[α-15N]amino acids. The stereoselective electophillic hydroxyamination of (S)-acylbornane-10,2-sultams, followed by Zn(o)/H+ reduction, and alkaline cleavag

CONTROLLING STEREOCHEMISTRY IN RADICAL ADDITION AND CYCLIZATION REACTIONS WITH OPPOLZER'S CAMPHOR SULTAM

Acrylate derivatives of Oppolzer's camphor sultam exhibit good to excellent levels of stereoselectivity in typical radical allylations and alkene and alkyne cyclizations.

Asymmetric Synthesis of α-Amino Acids and α-N-Hydroxyamino Acids from N-Acylbornane-10,2-sultams: 1-Chloro-1-nitrosocyclohexane as a Practical +> Equivalent

Successive treatment of N-acylsultams 3 with sodium hexamethyldisilazide, 1-chloro-1-nitrosocyclohexane (1), and aq.HCl gave diastereoisomerically pure, crystalline N-hydroxyamino-acid derivatives 5.These were converted into various amino acids 7, N-hydroxyamino acids 8, and an N-Boc-amino acid 9. (S,S)-Isoleucine (17) and (S,S)-2-acetamido-3-phenylbutyric acid (23) were obtained from N-crotonoylsultam 15 via 1,4-addition of an organomagnesium or organocopper reagent followed by enolate 'amination' with 1.