2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, monohydrochloride, [4S-(4alpha,4aalpha,5alpha,5aalpha,6beta,12aalpha)]-

Base Information

• Chemical Name: 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, monohydrochloride, [4S-(4alpha,4aalpha,5alpha,5aalpha,6beta,12aalpha)]-
• CAS No.: 41411-66-9
• Molecular Formula: C22H24N2O8.ClH
• Molecular Weight: 480.902
• Mol file: 41411-66-9.mol

Synonyms:2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, monohydrochloride, 4S-(4.alpha.,4a.alpha.,5.alpha.,5a.alpha.,6.beta.,12a.alpha.)-;DOXYCYCLINE 6-EPIMER HCL;6-epidoxycline hydrochloride

Chemical Property of 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, monohydrochloride, [4S-(4alpha,4aalpha,5alpha,5aalpha,6beta,12aalpha)]-

Chemical Property:

• PSA: 181.62000
• LogP: 1.15470

Purity/Quality:

97% ^*data from raw suppliers

6-Epidoxycycline hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Use Description: 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, monohydrochloride, [4S-(4α,4aα,5α,5aα,6β,12aα)]-, is a complex compound with significant applications in several fields. In the pharmaceutical industry, it plays a vital role as a key ingredient in the production of tetracycline antibiotics. Tetracyclines are widely used to treat bacterial infections, and 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, monohydrochloride, [4S-(4alpha,4aalpha,5alpha,5aalpha,6beta,12aalpha)]- serves as their core structure, contributing to their antibiotic properties. Additionally, in the field of microbiology and life sciences, it is employed as a tool for bacterial selection and research due to its antibiotic properties. Furthermore, in clinical medicine, it may find applications in the treatment of bacterial infections, highlighting its importance in healthcare and therapeutic interventions. Its role as a core structure for antibiotics underscores its critical significance in the pharmaceutical and medical fields, particularly in the fight against bacterial diseases and infections.

Technology Process of 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, monohydrochloride, [4S-(4alpha,4aalpha,5alpha,5aalpha,6beta,12aalpha)]-

There total 17 articles about 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-, monohydrochloride, [4S-(4alpha,4aalpha,5alpha,5aalpha,6beta,12aalpha)]- 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: 90.0%

C37H34N2O10 → doxycycline hydrochloride (10592-13-9,41411-66-9,564-25-0,61281-03-6)

Guidance literature:

C₃₇H₃₄N₂O₁₀; With hydrogen; palladium; In tetrahydrofuran; methanol; at 23 ℃; for 2h; under 760.051 Torr;

With hydrogenchloride; In methanol; water; HPLC;

DOI:10.1021/ja806629e

Reference yield: 90.0%

doxycycline (564-25-0,10597-92-9,7164-70-7,7264-10-0) → doxycycline hydrochloride (10592-13-9,41411-66-9,564-25-0,61281-03-6)

Guidance literature:

With hydrogenchloride; In methanol; water;

Reference yield:

(1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid (32359-20-9) → doxycycline hydrochloride (10592-13-9,41411-66-9,564-25-0,61281-03-6)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 3-chloro-benzenecarboperoxoic acid / ethyl acetate / 10.5 h / 23 °C / Inert atmosphere

2.1: methanol; hexane; benzene / 0.08 h / 23 °C / Inert atmosphere

2.2: 0.5 h

3.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 °C / Inert atmosphere

4.1: lithium trifluoromethanesulfonate / toluene / 3 h / 23 - 60 °C / Inert atmosphere

4.2: 18 h / 23 °C / Inert atmosphere

5.1: triphenylphosphine; carbon tetrabromide / acetonitrile / 0.33 h / 0 - 23 °C

6.1: triethylamine / acetonitrile / 0.5 h / 0 - 23 °C

7.1: (1R)-(-)-(8,8-dichloro-10-camphorsulfonyl) oxaziridine / dichloromethane / 20 h / 23 °C

8.1: phosphorous acid trimethyl ester / methanol / 36 h

9.1: dmap / dichloromethane / 2 h / 23 °C

10.1: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 23 °C

11.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 12 h / 23 °C / Darkness

12.1: triethylamine / tetrahydrofuran / 0.67 h / 0 °C

13.1: N,N,N,N,-tetramethylethylenediamine; n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 1.25 h / -78 °C / Inert atmosphere

13.2: 2 h / -75 - 0 °C / Inert atmosphere

14.1: hydrogen fluoride; water / acetonitrile / 60 h / 23 °C / Inert atmosphere

15.1: palladium; hydrogen / methanol; tetrahydrofuran / 2 h / 23 °C / 760.05 Torr

15.2: Inert atmosphere

With dmap; n-butyllithium; carbon tetrabromide; N,N,N,N,-tetramethylethylenediamine; 2-iodoxybenzoic acid; hydrogen fluoride; tetrabutyl ammonium fluoride; water; hydrogen; lithium trifluoromethanesulfonate; palladium; acetic acid; (1R)-(-)-(8,8-dichloro-10-camphorsulfonyl) oxaziridine; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile; benzene; 13.1: |Michael Addition / 13.2: |Dieckmann Condensation;

upstream raw materials:

doxycycline

(1S,2R)-1,2-dihydroxycyclohexa-3,5-diene-1-carboxylic acid

(1S,2R,3S,6R)-2,3-Dihydroxy-7-oxa-bicyclo[4.1.0]hept-4-ene-3-carboxylic acid

(1S,2R,3R,6S)-2,3-Bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[4.1.0]hept-4-ene-1-carboxylic acid methyl ester

Downstream raw materials:

doxycycline

malonic acid

(4S,4aR,5S,5aR,6R,12aS)-3,5,10,12,12a-pentahydroxy-6-methyl-4-(methylamino)-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide