78173-89-4

Basic information

• Product Name: methyl (1R,2R,4S)-2,4,5,7-tetrahydroxy-2-methyl-6,11-dioxo-3,4-dihydro -1H-tetracene-1-carboxylate
• Synonyms: methyl (1R,2R,4S)-2,4,5,7-tetrahydroxy-2-methyl-6,11-dioxo-3,4-dihydro -1H-tetracene-1-carboxylate;auramycinone;(1R)-1,2,3,4,6,11-Hexahydro-2α,4α,5,7-tetrahydroxy-2-methyl-6,11-dioxo-1-naphthacenecarboxylic acid methyl ester;(1R,2R,4S)-2-Methyl-1,2,3,4,6,11-hexahydro-2,4,5,7-tetrahydroxy-6,11-dioxo-1-naphthacenecarboxylic acid methyl ester
• CAS NO: 78173-89-4
• Molecular Formula: C21H18O8
• Molecular Weight: 398.3628
• Mol File: 78173-89-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 659.7°Cat760mmHg
• Flash Point: 236.7°C
• Appearance: /
• Density: 1.576g/cm³
• Vapor Pressure: 2.66E-18mmHg at 25°C
• Refractive Index: 1.702
• CAS DataBase Reference: methyl (1R,2R,4S)-2,4,5,7-tetrahydroxy-2-methyl-6,11-dioxo-3,4-dihydro -1H-tetracene-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (1R,2R,4S)-2,4,5,7-tetrahydroxy-2-methyl-6,11-dioxo-3,4-dihydro -1H-tetracene-1-carboxylate(78173-89-4)
• EPA Substance Registry System: methyl (1R,2R,4S)-2,4,5,7-tetrahydroxy-2-methyl-6,11-dioxo-3,4-dihydro -1H-tetracene-1-carboxylate(78173-89-4)

Safety Data

• Hazardous Substances Data: 78173-89-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H18O8/c1-21(28)7-12(23)14-9(16(21)20(27)29-2)6-10-15(19(14)26)18(25)13-8(17(10)24)4-3-5-11(13)22/h3-6,12,16,22-23,26,28H,7H2,1-2H3/t12-,16-,21+/m0/s1

Upstream product

• 95455-76-8 methyl (6a-SR,9-RS,10-RS,10a-RS)-12-t-butyldimethylsilyloxy-5,9-dihydroxy-4-methoxy-9-methyl-6-oxo-6,6a,7,8,9,10,10a,11-octahydronaphthacene-10-carboxylate 
• 95455-52-0 (+/-)-7-deoxy-5,7-di-O-ethyl auramycinone 
• 95455-86-0 (+/-)-4-O-methyl-7-deoxyauramycinone 
• 95455-99-5 methyl 4-(1'-t-butyldimethylsilyloxy-4'-hydroxy-5'-methoxy-3'-(5''-oxohexanoyl)naphth-2'-yl)-2-butenoate 
• 95456-10-3 3-(5,5-ethylenedioxy-2-hexenoyl)-1,5-dimethoxy-4-methoxymethoxynaphthalene 
• 95456-09-0 3-acetyl-1,5-dimethoxy-4-methoxymethoxynaphthalene 
• 95455-94-0 5-methoxy-3-(5-oxohexanoyl)-1,4-naphthoquinone 
• 81418-41-9 1-(1-hydroxy-4,8-dimethoxynaphthalen-2-yl)ethanone 
• 78173-93-0 (+/-)-7-deoxyauramycinone 

Relevant articles and documents

Synthesis of (+/-)-aklavinone and (+/-)-auramycinone via electrondeficient o-quinonoid pyrones

Dehydration of the formyl acid 3 (R = H) with acetic anhydride in benzene at 80 deg C generates the quinonoid pyrone 4 which can be trapped with norbornadiene, N-phenylmaleimide and enol silyl ethers; the adduct 6 (R = Me, P = TES) and its 9-epimer 10 from 2-(triethylsilyloxy)propene are readily transformed into (+/-)-auramycinone 2 (R = Me) whilst those from 2-(triethylsilyloxy)buta-1,3-diene are readily converted into the methyl ethers 24, 25, 33 and 34 of which 24, 33 and 34 are known to be readily converted into (+/-)-aklavinone 2 (R = Et).

A general and regiospecific route to tetracyclic alkenes in the 11-deoxyanthracyclinone series. Application to the total synthesis of (±)-auramycinone

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