136949-08-1

Basic information

• Product Name: 7-O-<(R)-α-Methoxy-α-(trifluoromethyl)phenylacetyl>daunomycinone
• CAS NO: 136949-08-1
• Molecular Weight: 614.529
• Mol File: 136949-08-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 7-O-<(R)-α-Methoxy-α-(trifluoromethyl)phenylacetyl>daunomycinone(CAS DataBase Reference)
• NIST Chemistry Reference: 7-O-<(R)-α-Methoxy-α-(trifluoromethyl)phenylacetyl>daunomycinone(136949-08-1)
• EPA Substance Registry System: 7-O-<(R)-α-Methoxy-α-(trifluoromethyl)phenylacetyl>daunomycinone(136949-08-1)

Safety Data

• Hazardous Substances Data: 136949-08-1(Hazardous Substances Data)

Upstream product

• 136949-07-0 (7S,9S)-9-Ethynyl-7,8,9,10-tetrahydro-6,9,11-trihydroxy-4-methoxy-7-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)naphthacene-5,12-dione 
• 136949-06-9 (6aR,7S,10aR)-6a,7,8,9,10,10a-Hexahydro-5,12-dihydroxy-4-methoxy-7-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)naphthacene-6,9,11-trione 
• 137036-35-2 (7S,9S)-9-Ethynyl-7,8,9,10-tetrahydro-6,7,9,11-tetrahydroxy-4-methoxynaphthacene-5,12-dione 
• 21794-55-8 (+)-Daunomycinone 
• 39637-99-5 (S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride 

Relevant articles and documents

Studies Related to Anthracyclines. Part 3. Stereoselective Synthesis of (+)-Daunomycinone

The title compound 2b was prepared by a seven-step sequence from (+/-)-4a,9a-epoxy-4a,9a-dihydro-5-methoxyanthracene-1,4,9,10-tetraone 3b/3c and (E)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-trimethylsilyloxybuta-1,3-diene 4.Acidic hydrolysis of the crude Diels-Alder cycloadducts of compounds 3b/3c and 4 led, after fractional crystallisation, to the isolation of (5aS,6aR,7S,10aR,11aR)-5a,11a-epoxy-4-methoxy-5a,6a,7,8,9,10,10a,11a-octahydro-7-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)naphthacene-5,6,9,11,12-pentaone 6b.The last-cited compound was transformed into (+)-daunomycinone 2b by reduction, ethynylation, oxida tion, hydrolysis and hydration steps.