117620-87-8

Basic information

• Product Name: MM 47755
• Synonyms: MM 47755;(-)-3,4-Dihydro-3-hydroxy-8-methoxy-3-methylbenz[a]anthracene-1,7,12(2H)-trione;(-)-8-O-Methyltetrangomycin;6-Deoxy-8-O-methylrabelomycin;8-O-Methyltetrangomycin
• CAS NO: 117620-87-8
• Molecular Formula: C20H16O5
• Molecular Weight: 336.338
• Mol File: 117620-87-8.mol

Chemical Properties

• Melting Point: 169-170℃
• Boiling Point: 583.3°Cat760mmHg
• Flash Point: 214.3°C
• Appearance: /
• Density: 1.39g/cm³
• Vapor Pressure: 1.89E-14mmHg at 25°C
• Refractive Index: 1.652
• Storage Temp.: ?20°C
• PKA: 14.02±0.20(Predicted)
• CAS DataBase Reference: MM 47755(CAS DataBase Reference)
• NIST Chemistry Reference: MM 47755(117620-87-8)
• EPA Substance Registry System: MM 47755(117620-87-8)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-50
• Safety Statements: 61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 117620-87-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H16O5/c1-20(24)8-10-6-7-12-17(15(10)13(21)9-20)19(23)11-4-3-5-14(25-2)16(11)18(12)22/h3-7,24H,8-9H2,1-2H3

Upstream product

• 169128-03-4 3-Hydroxy-8-methoxy-3-methyl-1,2,3,4-tetrahydrobenzanthracene-7,12-dione 
• 188398-55-2 1-Acetyl-5-methoxy-2-(2-oxo-propyl)-anthraquinone 
• 188398-47-2 1-Acetyl-5-methoxy-2-(2-methyl-[1,3]dioxolan-2-ylmethyl)-anthraquinone 
• 169128-01-2 (+/-)-3-(dimethylfluorosilanyl)-8-hydroxy-3-methyl-1,2,3,4-tetrahydrobenzanthracene-7,12-dione 
• 169128-02-3 3-Dimethylfluorosilanyl-8-methoxy-3-methyl-1,2,3,4-tetrahydrobenzanthracene-7,12-dione 
• 1379673-93-4 5-(methoxymethoxy)-5-methyloct-1-en-7-yne 
• 109-49-9 5-Hexen-2-one 
• 267432-89-3 5-[(Methoxymethyl)oxy]-5-methyl-1-vinylcyclohexene 
• 76329-07-2 4-methyloct-7-en-1-yn-4-ol 
• 600155-08-6 (3S)-3-hydroxy-8-methoxy-3-methyl-1,2,3,4-tetrahydro-benz[a]anthracene-7,12-dione 
• 949087-78-9 (S)-3-(4-methoxybenzyloxy)-8-hydroxy-3-methyl-1,2,3,4-tetrahydrotetraphene-7,12-dione 
• 949087-79-0 (S)-8-methoxy-3-(4-methoxybenzyloxy)-3-methyl-1,2,3,4-tetrahydrotetraphene-7,12-dione 
• 888481-28-5 (3S)-tert-butyl-(8-methoxy-3-methyl-1,2,3,4-tetrahydro-benz[a]anthracen-3-yloxy)-dimethyl-silane 
• 888481-29-6 (3S)-3-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-3-methyl-1,2,3,4-tetrahydro-benz[a]anthracene-7,12-dione 

Downstream Products

• 85178-50-3 1-Hydroxy-8-methoxy-3-methylbenzanthracene-7,12-dione 

Relevant articles and documents

A unified strategy for the syntheses of angucyclinone antibiotics: Total syntheses of tetrangulol, kanglemycin M, X-14881-E, and anhydrolandomycinone

A unified strategy for the syntheses of angucyclinone antibiotics was developed utilizing sequential intramolecular enyne metathesis, Diels-Alder/aromatization, photooxygenation, and one-pot elimination/ aromatization reactions. The diversity in this sequ

The cobalt way to angucyclinones: Asymmetric total synthesis of the antibiotics (+)-rubiginone B2, (-)-tetrangomycin, and ( - ) -8- O-Methyltetrangomycin

A cobalt(I)-mediated convergent and asymmetric total synthesis of angucyclinones with an aromatic B ring has been developed. In the course of our research, we synthesized three naturally occurring anguclinone derivatives, namely, (+)-rubiginone B2/s

Angucyclinone antibiotics: Total syntheses of YM-181741, (+)-ochromycinone, (+)-rubiginone B2, (-)-tetrangomycin, and MM-47755

(Chemical Equation Presented) A concise and highly enantioselective route has been developed for the synthesis of angucyclinone-type natural products. Utilizing this strategy, total syntheses of five natural products YM-181741, (+)-ochromycinone, (+)-rubi

Total synthesis of (-)-8-O-methyltetrangomycin (MM 47755)

A stereoselective total synthesis of the natural antibiotic (-)-8-O-methyltetrangomycin 1 is reported. The essential steps for this convergent synthesis are the transformation of a geraniol epoxide into a chiral octadiyne derivative, which was converted i

Remote stereochemical control in asymmetric Diels-Alder reactions: Synthesis of the angucycline antibiotics, (-)-tetrangomycin and MM 47755

The first asymmetric syntheses of the angucycline antibiotics, (-)-tetrangomycin and MM 47755, are achieved via a short efficient sequence starting from the chiral Lewis acid promoted Diels-Alder reaction of 5-hydroxy-1,4-naphthoquinone and (±)-(E)-5-dimethylphenylsilyl-5-methyl-1-(2′- trimethylsiloxyvinyl)cyclohexene 7 where an effective kinetic resolution of the latter, controlled by its remote stereocentre, is described.

Synthesis of angucyclines. 8. Biomimetic-type synthesis of rabelomycin, tetrangomycin, and related ring B aromatic angucyclinones

The angucyclinones with aromatic ring B (1a-c and 2a-c) are prepared in a biomimetic-type synthesis by two successive aldol cyclizations starting from the substituted naphthoquinones 12a-c. In both cyclization steps the C-H acidity of the potential nucleophilic centers determines the mode of cyclization under kinetically controlled conditions. The tetrahydroanthraquinones 13a-c/14a-c are hydroxylated at C-4 to the phenolic anthraquinones 16a-c upon treatment with excess NMO.

Synthesis of Naturally (MM 47755; X-14881 E) and Non-Naturally Occuring Aromatic Angucyclinones

The Diels-Alder reactions of the naphthoquinones 1-4 with the dienes 5a-7 were investigated.The regioisomeric outcome of the adducts 10a-10g, 16, and 23 is in agreement with theoretical predictions from frontier orbital calculations.The adduct 10a was further converted to the non-natural (e.g. 15) and the adduct 16 to the natural angucyclinones MM 47755 (19a) and X-14881 E (22) by silicon-oxygen exchange and photooxygenation.The addition of naphthoquinones 2 and 4 to dienes 6 and 7 afford the Diels-Alder adducts 16 and 23, respectively, which are valuable intermediates for further transformation into non-aromatic angucyclinones. - Keywords: Angucyclinones / MM 47755 / X-14881 E / Diels-Alder reactions / Silicon-oxygen exchange