163564-92-9

Basic information

• Product Name: RATJADONE A
• Synonyms: RATJADON;RATJADONE;RATJADONE A
• CAS NO: 163564-92-9
• Molecular Formula: C28H40O5
• Molecular Weight: 456.6142
• Mol File: 163564-92-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 640.8°C at 760 mmHg
• Flash Point: 206.8°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 4.02E-19mmHg at 25°C
• Refractive Index: 1.587
• CAS DataBase Reference: RATJADONE A(CAS DataBase Reference)
• NIST Chemistry Reference: RATJADONE A(163564-92-9)
• EPA Substance Registry System: RATJADONE A(163564-92-9)

Safety Data

• Hazardous Substances Data: 163564-92-9(Hazardous Substances Data)

Usage

Uses

Ratjadone A, Synthetic is a cell-permeable polyketide that inhibits cell proliferation.

InChI:InChI=1/C28H40O5/c1-6-9-26-22(5)25(30)18-27(33-26)24(29)12-7-10-19(2)16-21(4)17-20(3)14-15-23-11-8-13-28(31)32-23/h6-10,12-15,17,21-27,29-30H,11,16,18H2,1-5H3/b9-6+,12-7+,15-14+,19-10+,20-17-/t21-,22+,23-,24-,25-,26+,27+/m1/s1

Upstream product

• 321994-96-1 cis-5,6-dihydro-6-(hydroxymethyl)-2-methoxy-2H-pyran 
• 343262-80-6 (5S,10S,16S)-(6E,8Z,12E,14E)-3-benzenesulfonyl-16-(tert-butyldimethylsilanoxy)-16-[(E)-(2R,4S,5S,6R)-4-(tert-butyldimethylsilanoxy)-5-methyl-6-propenyltetrahydropyranyl]-5-triethylsilanoxy-8,10,12-trimethylhexadeca-6,8,12,14-tetraen-1-ol 
• 343263-00-3 (5S,10S,16S)-(6E,8Z,12E,14E)-3-benzenesulfonyl-16-(tert-butyldimethylsilanoxy)-16-[(E)-(2R,4S,5S,6R)-4-(tert-butyldimethylsilanoxy)-5-methyl-6-propenyltetrahydropyranyl]-5-triethylsilanoxy-8,10,12-trimethylhexadeca-6,8,12,14-tetraen-1-al 
• 343262-79-3 (2R,3S,4S,6R)-6-[(1S,7S,12S)-(2E,4E,8Z,10E)-14-benzenesulfonyl-1-(tert-butyldimethylsilanoxy)-12-triethylsilanoxy-5,7,9-trimethyltetradeca-2,4,8,10-tetraenyl]-4-(tert-butyldimethylsilanoxy)-3-methyl-2-E-propenyltetrahydropyran 
• 343262-78-2 2,2-dimethylpropionic acid (1S,6S,12S)-(2E,4Z,8E,10E)-1-(2-benzenesulfonylethyl)-12-(t-butyldimethylsilanoxy)-12-((E)-(2R,4S,5S,6R)-5-methyl-6-propenyl-4-(t-butyldimethylsilanoxy)-tetrahydropyran-2-yl)-4,6,8-trimethyldodeca-2,4,8,10-tetraenyl ester 
• 343263-02-5 (6S)-4-benzenesulfonyl-6-{(5S,11S)-(1E,3Z,7E,9E)-11-(tert-butyldimethylsilanoxy)-11-[(E)-(2R,4S,5S,6R)-4-(tert-butyldimethylsilanoxy)-5-methyl-6-propenyltetrahydropyran-2-yl]-3,5,7-trimethylundeca-1,3,7,9-teraenyl}-tetrahydropyran-2-one 
• 343263-01-4 (6S)-4-benzenesulfonyl-6-{(5S,11S)-(1E,3Z,7E,9E)-11-(tert-butyldimethylsilanoxy)-11-[(E)-(2R,4S,5S,6R)-4-(tert-butyldimethylsilanoxy)-5-methyl-6-propenyltetrahydropyran-2-yl]-3,5,7-trimethylundeca-1,3,7,9-teraenyl}-tetrahydropyran-2-ol 
• 343262-99-7 (1S,6S,12S)-(2E,4Z,8E,10E)-1-(2-benzenesulfonylethyl)-12-(t-butyldimethylsilanoxy)-12-((E)-(2R,4S,5S,6R)-5-methyl-6-propenyl-4-(t-butyldimethylsilanoxy)-tetrahydropyran-2-yl)-4,6,8-trimethyldodeca-2,4,8,10-tetraen-1-ol 
• 343262-88-4 2,2-dimethylpropionic acid (E)-(2S,3S,5S,6R,7R)-7-(tert-butyldiphenylsilanoxy)-2,3-epoxy-5-(4-methoxybenzyloxy)-6-methyldeca-8-enyl ester 
• 343262-59-9 (E)-(2S,3S,5S,6R,7R)-7-(tert-butyldiphenylsilanoxy)-2,3-epoxy-5-(4-methoxybenzyloxy)-6-methyldeca-8-en-1-ol 
• 343262-84-0 (E)-(4S,5R,6S)-6-(tert-butyldiphenylsilanoxy)-4-(4-methoxybenzyloxy)-5-methylnon-7-ene-1,2-diol 
• 343262-86-2 (2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-dienoic acid methyl ester 
• 343262-87-3 (2E,8E)-(5S,6R,7S)-7-(tert-butyldiphenylsilanoxy)-5-(4-methoxybenzyloxy)-6-methyldeca-2,8-dien-1-ol 
• 343262-81-7 (4S)-3-[(E)-(2S,3S)-3-(tert-butyldiphenylsilanoxy)-2-methyl-1-oxo-4-hexen-1-yl]-4-(phenylmethyl)-1,3-oxazolidin-2-one 

Relevant articles and documents

The first total synthesis of (+)-ratjadone

The first total synthesis of ratjadone was achieved using a highly convergent approach joining three subunits together with a Wittig olefination and a selective Heck reaction as the pivotal steps. Besides establishing a robust and reliable route for the synthesis of this orphan ligand, the configuration of unknown stereocenters could also be determined. This synthesis not only provides an additional access to a biologically important compound but also enables the synthesis structural analogues for biological target identification.

Total synthesis of (+)-ratjadone

The coupling of three fragmeats by a wittig olefination and a subsequent selective Heck reaction are the pivotal steps in the the first total synthesis of ratjadone (see picture), a cytotoxic as well as antibiotically effective polyketide. This synthesis enabled the elucidation of the absolute configuration of the natural product. In this way it should also be possible to synthesize structural analogues with which the various cellular processes mediated by ratjadone can be studied.