HMR 1826

Base Information

• Chemical Name: HMR 1826
• CAS No.: 148580-25-0
• Molecular Formula: C41H42 N2 O22
• Molecular Weight: 914.785
• Mol file: 148580-25-0.mol

Synonyms:5,12-Naphthacenedione,7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-10-[[2,3,6-trideoxy-3-[[[[4-(b-D-glucopyranuronosyloxy)-3-nitrophenyl]methoxy]carbonyl]amino]-a-L-lyxo-hexopyranosyl]oxy]-,(8S-cis)-; F 826; HMR 1826

Chemical Property of HMR 1826

Chemical Property:

• PSA: 380.65000
• LogP: 0.06230

Purity/Quality:

99% ^*data from raw suppliers

HMR1826 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: As a heterodimeric lucuronide prodrug of doxorubicin (D558000), an anthracycline antibiotic and HMR 1826 is commonly used in the treatment of wide range of cancers. A heterodimeric lucuronide prodrug of doxorubicin (D558000), an anthracycline antibiotic and are commonly used in the treatment of wide range of cancers.

Technology Process of HMR 1826

There total 8 articles about HMR 1826 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: 80.0%

C42H44N2O22 → N-[4-O-β-D-glucuronyl-3-nitrobenzyloxycarbonyl]doxorubicin (148580-25-0)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at -10 ℃; for 0.0833333h;

DOI:10.1021/jm970589l

Reference yield:

doxorubicin (23214-92-8) → N-[4-O-β-D-glucuronyl-3-nitrobenzyloxycarbonyl]doxorubicin (148580-25-0)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / dimethylformamide / 2 h / Ambient temperature

2: 95 percent / NaOMe, MeOH / dimethylformamide; tetrahydrofuran / 0 °C

3: 80 percent / 2 N aq. NaOH / tetrahydrofuran / 0.08 h / -10 °C

With methanol; sodium hydroxide; sodium methylate; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm970589l

Reference yield:

4-hydroxy-3-nitrobenzaldehyde (3011-34-5) → N-[4-O-β-D-glucuronyl-3-nitrobenzyloxycarbonyl]doxorubicin (148580-25-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / silver oxide / acetonitrile / 4 h / Ambient temperature

2: 99 percent / NaBH₄, silica gel HL₆₀ / CHCl₃; propan-2-ol / 0.75 h / 0 °C

3: Et₃N / CH₂Cl₂; acetonitrile / 1.5 h / 0 °C

4: Et₃N / dimethylformamide / 2 h / Ambient temperature

5: 95 percent / NaOMe, MeOH / dimethylformamide; tetrahydrofuran / 0 °C

6: 80 percent / 2 N aq. NaOH / tetrahydrofuran / 0.08 h / -10 °C

With methanol; sodium hydroxide; sodium tetrahydroborate; sodium methylate; silica gel; triethylamine; silver(l) oxide; In tetrahydrofuran; dichloromethane; chloroform; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile;

DOI:10.1021/jm970589l

upstream raw materials:

doxorubicin

4-hydroxy-3-nitrobenzaldehyde

(2S,3R,4S,5S,6S)-2-(4-formyl-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

(25,3R,45,55,65)-2-(4-(hydroxymethyl)-2-nitrophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Downstream raw materials:

doxorubicin

Refernces