Nanaomycin A methyl ester

Base Information

• Chemical Name: Nanaomycin A methyl ester
• CAS No.: 58286-56-9
• Molecular Formula: C₁₇H₁₆O₆
• Molecular Weight: 316.31
• Mol file: 58286-56-9.mol

Synonyms:trans-methyl (3,4-dihydro-5,10-dioxo-9-hydroxy-1-methyl-1H-naphtho(2,3-c)pyran-3-yl)acetate;trans-methyl (3,4-dihydro-5,10-dioxo-9-hydroxy-1-methyl-1H-naphtho[2,3-c]pyran-3-yl)acetate;nanaomycin A methyl ester;

Chemical Property of Nanaomycin A methyl ester

Chemical Property:

• PSA: 89.90000
• LogP: 1.80830

Purity/Quality:

99% ^*data from raw suppliers

NanaomycinalphaA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Nanaomycin alphaA is a selective Dnmt3b inhibitor with antibiotic, antimycoplasmic, and antifugal properties.

Technology Process of Nanaomycin A methyl ester

There total 34 articles about Nanaomycin A methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

trans-methyl <9-methoxy-1-methyl-5,10-dioxo-3,4,5,10-tetrahydro-1H-naphtho<2,3-c>pyran-3-yl>acetate (78340-69-9) → nanaomycin A methyl ester (124438-93-3,58286-56-9,73804-45-2,73804-46-3,78340-70-2)

Guidance literature:

With aluminium trichloride; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1246/cl.1982.609 DOI:10.1021/jo00353a015

Reference yield: 89.0%

cis-methyl <9-methoxy-1-methyl-5,10-dioxo-3,4,5,10-tetrahydro-1H-naphtho<2,3-c>pyran-3-yl>acetate (78340-68-8) → nanaomycin A methyl ester (124438-93-3,58286-56-9,73804-45-2,73804-46-3,78340-70-2)

Guidance literature:

With boron tribromide; In dichloromethane; 1.) -78 deg C, 5 min, 2.) 0 deg C, 10 min;

Reference yield: 78.0%

1-acetoxy-1,3-butadiene (1515-76-0) + (+)-methyl 2-[(1S,3R)-5,8-dioxo-1-methyl-3,4-dihydro-1H-benzopyran-3-yl]acetate (1246659-64-2) → nanaomycin αA (58286-56-9)

Guidance literature:

1-acetoxy-1,3-butadiene; (+)-methyl 2-[(1S,3R)-5,8-dioxo-1-methyl-3,4-dihydro-1H-benzopyran-3-yl]acetate; In toluene; at 20 ℃; for 48h;

With sodium carbonate; In ethanol; water; at 20 ℃; for 5h;

DOI:10.1002/ejoc.201000476

upstream raw materials:

acetic anhydride

3,4-Dihydro-9-hydroxy-5,10-dimethoxy-1-methyl-1H-naphtho<2,3-c>pyran-3-essigsaeure-methylester

1-(trimethylsiloxy)-1-methoxy-1,3-butadiene

trans-methyl (7-bromo-3,4-dihydro-5,8-dioxo-1-methyl-1H-2-benzopyran-3-yl)acetate

Downstream raw materials:

9-Benzyloxy-3,4-dihydro-5,10-dimethoxy-1-methyl-1H-naphtho<2,3-c>pyran-3-essigsaeure-methylester

9-Benzyloxy-3,4-dihydro-5,10-dimethoxy-1-methyl-1H-naphtho<2,3-c>pyran-3-essigsaeure

Refernces

• 1、 Brimble, Margaret A.,Lynds, Sara M.. "A Short Synthesis of Deoxyfrenolicin". . p. 493 - 496. Retrieved 2007/10/02.
• 2、 Laatsch, Hartmut. "Dimeric Naphthoquinones, XX.- Partial Synthesis of Actinorhodine". . p. 297 - 304. Retrieved 2007/10/02.