99907-83-2

Basic information

• Product Name: 2-Naphthalenecarboxylic acid, 2-amino-1,2,3,4-tetrahydro-5,8-dimethoxy-, methyl ester, (R)-
• Synonyms: (R)-2-Amino-5,8-dimethoxy-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid methyl ester
• CAS NO: 99907-83-2
• Molecular Formula: C14H19NO4
• Molecular Weight: 265.30500
• Mol File: 99907-83-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Naphthalenecarboxylic acid, 2-amino-1,2,3,4-tetrahydro-5,8-dimethoxy-, methyl ester, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Naphthalenecarboxylic acid, 2-amino-1,2,3,4-tetrahydro-5,8-dimethoxy-, methyl ester, (R)-(99907-83-2)
• EPA Substance Registry System: 2-Naphthalenecarboxylic acid, 2-amino-1,2,3,4-tetrahydro-5,8-dimethoxy-, methyl ester, (R)-(99907-83-2)

Safety Data

• Hazardous Substances Data: 99907-83-2(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 99907-84-3 2-amino-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthoic acid 
• 37464-90-7 5,8-dimethoxy-2-tetralone 
• 99907-80-9 methyl 2-amino-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthoate 

Downstream Products

• 110267-81-7 Amrubicin 
• 86264-76-8 (R)-(-)-9-acetamido-9-<1,1-(ethylenedioxy)ethyl>-6,11-dihydroxy-7,8,9,10-tetrahydro-5,12-naphthacenedione 
• 86264-61-1 (R)-(-)-2-acetyl-2-acetamido-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene 

Relevant articles and documents

Amrubicin hydrochloride intermediate compound I-2

The invention belongs to the field of medicine synthesis, and provides a new intermediate and an amrubicin hydrochloride important intermediate synthesized by using the intermediate. The problem of low yield caused by chiral resolution of the amrubicin intermediate in the prior art is solved, and the new intermediate compound synthesized by chirality has the advantages of high yield, simple operation, significantly reduced production cost, and suitableness for industrial production.

Amrubicin hydrochloride intermediate compound I-4

The invention belongs to the technical field of medicines, and particularly relates to an amrubicin hydrochloride intermediate compound and a preparation method thereof. A novel intermediate is provided and is used for synthesizing the amrubicin hydrochloride important intermediate. The preparation method solves the problem of low yield caused by chiral resolution of the amrubicin intermediate inthe prior art, and the new intermediate compound synthesized through chirality has the advantages of high product yield, simple operation, substantial reduction of the production cost, and suitableness for industrial production.

Stereospecific Total Synthesis of 9-Aminoanthracyclines: (+)-9-Amino-9-deoxydaunomycin and Related Compounds

9-amino-9-deoxydaunomycin and related compounds, in which the hydroxyl group at the 9-position of daunomycin is replaced by an amino group, have been synthesized.Asymmetry was introduced into the synthetic sequence for the AB synthon by resolution of the intermediate amino ester or acetamido acid to afford (R)-(-)-2-acetyl-2-acetamido-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene, which was converted to the tetracyclic amido ketones by Friedel-Crafts acylation with phthalic anhydride or its 3-methoxy derivative.The resulting regioisomers 4- and 1-methoxy compounds were separed, after methylation and selective demethylation, by crystallization and preparative TLC.The required introduction of the C7-hydroxyl function proceeded stereosepcifically via a three-step reaction sequence involving formation of an oxazine compound.The silver trifluoromethane assisted glycosidation of the resulting aglycons with 2-deoxy-3,4-di-O-acetyl-D-erythro-pentopyranosyl bromide or N,O-bis(trifluoroacetyl)daunosaminyl chloride, followed by alkaline hydrolysis afforded the target glycosides.The work reported herein comprises an efficient, practical synthesis of 9-amino-9-deoxydaunomycin and its analogues with the same stereochemistry as in the naturally occurring anthracyclines.