151519-02-7

Basic information

• Product Name: PIRONETIN
• Synonyms: PIRONETIN
• CAS NO: 151519-02-7
• Molecular Formula: C₁₉H₃₂O₄
• Molecular Weight: 324.45
• Product Categories: Antibiotic
• Mol File: 151519-02-7.mol

Chemical Properties

• Melting Point: 75-77 °C
• Boiling Point: 473.1 °C at 760 mmHg
• Flash Point: 160.3 °C
• Appearance: /
• Density: 0.993 g/cm³
• Vapor Pressure: 6.14E-11mmHg at 25°C
• Refractive Index: 1.478
• PKA: 14.28±0.20(Predicted)
• CAS DataBase Reference: PIRONETIN(CAS DataBase Reference)
• NIST Chemistry Reference: PIRONETIN(151519-02-7)
• EPA Substance Registry System: PIRONETIN(151519-02-7)

Safety Data

• Hazardous Substances Data: 151519-02-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Pironetin is used as an antifungal agent for its ability to inhibit the growth of fungi by disrupting their cell membranes and metabolic pathways.
Used in Oncology:
Pironetin is used as an antiproliferative agent for its potential to inhibit the growth of cancer cells, making it a candidate for the development of new drugs in oncology.
Used in Agricultural Industry:
Pironetin is used as a potential biocontrol agent for its antifungal properties, which can be applied to protect crops from fungal infections.

InChI:InChI=1/C19H32O4/c1-6-8-9-13(3)19(22-5)14(4)16(20)12-17-15(7-2)10-11-18(21)23-17/h6,8,10-11,13-17,19-20H,7,9,12H2,1-5H3/b8-6+/t13-,14-,15+,16+,17+,19+/m0/s1

Upstream product

• 172603-27-9 (5R,6R,2'R,3'R,4'R,5'S)-(7'E)-9'-5-Ethyl-5,6-dihydro-6-<4'-methoxy-2'-<(methoxymethyl)oxy>-3',5'-dimethyl-7'-nonenyl>-2H-pyran-2-one 
• 182744-62-3 (2Z,12E)-(4R,5R,7R,8R,9R,10S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-4-ethyl-9-methoxy-8,10-dimethyl-tetradeca-2,12-dienoic acid methyl ester 
• 191355-96-1 (2Z,4R,5R,7R,8S,9R,10S,12E)-4-ethyl-9-methoxy-8,10-dimethyl-2,12-tetradecadien-1,5,7-triol 
• 176109-74-3 acetic acid (E)-(1R,2S,3R,4S)-1-[(2R,3R)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-ylmethyl]-3-methoxy-2,4-dimethyloct-6-enyl ester 
• 943987-82-4 C₂₁H₃₆O₂Si 
• 943987-81-3 C₁₄H₃₀O₂Si 
• 943987-72-2 (3R,4R)-3-(tert-butyldimethylsilanyloxy)-4-ethyl-hex-5-enal 
• 1027084-13-4 C₁₂H₂₄OSi 
• 943987-73-3 C₂₅H₄₈O₄Si 
• 943987-74-4 C₂₆H₅₀O₄Si 
• 943987-76-6 acetic acid (E)-(1R,2S,3R,4S)-1-[(2R,3R)-3-ethyl-2-hydroxypent-4-enyl]-3-methoxy-2,4-dimethyloct-6-enyl ester 
• 943987-70-0 acrylic acid (E)-(1R,3R,4S,5R,6S)-3-acetoxy-1-[(R)-1-ethylallyl]-5-methoxy-4,6-dimethyldec-8-enyl ester 
• 1027312-06-6 C₁₅H₂₈N₂O 
• 943987-64-2 (E)-(S)-4-methyloct-6-en-3-one 

Relevant articles and documents

Stereoselective synthesis of (-) - Pironetin by an iterative prins cyclisation and reductive cleavage strategy

A stereoselective synthesis of pironetin, a natural product which is highly immunosuppressive and shows remarkable plant growth regulatory and antitumoral activities, is described. The approach avails successfully the high stereoselection of Prins cyclisation. The route relies, in addition, on the reductive opening of cyclic ethers, olefin metathesis, and lithium acetylide displacement of tosylate. Georg Thieme Verlag Stuttgart.

One-pot hydrosilylation-RCM-protodesilylation: Application to the synthesis of ω-alkenyl α,β-unsaturated lactones

A simple and efficient one-pot procedure has been developed for the synthesis of α,β-unsaturated lactones bearing a pendant E-olefin. This new methodology, which features a hydrosilylation, a ring-closing metathesis (RCM) and a protodesilylation reaction,

Asymmetric total synthesis of the immunosuppressant (-)-pironetin

(Chemical Equation Presented) A short, enantioselective total synthesis of the title compound 1 is described. The 14-step synthesis features a highly stereoselective Brown-type pentenylation and a onepot hydrosilylation/ring- closing metathesis (RCM)/prot

Asymmetric total synthesis of (-)-pironetin employing the SAMP/RAMP hydrazone methodology

A convergent asymmetric total synthesis of pironetin (1), a polyketide with immunosuppressive, antitumor, and plant-growth regulating activities is described. The synthesis was realized by coupling between the C 8-C14 2 and C7/

Catalytic asymmetric assembly of stereodefined propionate units: An enantioselective total synthesis of (-)-pironetin

Double diastereoselection in alkaloid-catalyzed acyl halide-aldehyde cyclocondensation (AAC) reactions provides a strategy for realizing syn- or anti-selective propionate aldol additions from a common reaction manifold. Matched AAC homologation of enantio

Total synthesis of the immunosupressant (-)-pironetin (PA48153C).

[reaction: see text]. Total synthesis of the immunosuppresant pironetin has been achieved by a synthetic route in which the connections between starting materials and the desired structure are readily discerned. Key steps include a diastereoselective Lewi

An efficient synthesis of pironetins employing a useful chiral building block, (1S, 5S, 6R)-5-hydroxybicyclo [4.1.0]heptan-2-one

A convergent total synthesis of pironetin 1 and related compound 2 using a chiral building block, (IS, 5S, 6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 5 is described. Both the dithiane 47 and the epoxide 32 with proper substituents were employed as coupling partners to construct the whole carbon skeleton 48, which was converted to (-)-pironetin 1 and (-)-2 in few steps. The usefulness of 5 for polyketide synthesis was demonstrated.

Total synthesis of (-)-pironetin

The convergent total synthesis of (-)-pironetin using a chiral building block, (1S, 5S, 6R)-5-hydroxybicyclo[4.1.0]heptan-2-one 5 is described. Both the dithiane 4 and the epoxide 2 with proper substituents were employed as coupling partners to construct the whole carbon skeleton 15, which was converted to pironetin 1 in a few steps.

Total synthesis of (-)-PA-48153C (pironetin) utilising L-quebrachitol as a chiral building block

The chiral and stereoselective synthesis of (-)-PA-48153C (pironetin) 1, a novel immunosuppressant, is described; the acyclic portion possessing four contiguous chiral centres in 1 was constructed stereoselectively from L-quebrachitol and the 2-pyranone m