N-[4-(daunorubicin-N-carbonyloxymethyl)-3-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate

Base Information

• Chemical Name: N-[4-(daunorubicin-N-carbonyloxymethyl)-3-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate
• CAS No.: 247075-44-1
• Molecular Formula: C₄₉H₅₁BrN₂O₂₃
• Molecular Weight: 1115.85

Synonyms:N-[4-(daunorubicin-N-carbonyloxymethyl)-3-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate

Chemical Property of N-[4-(daunorubicin-N-carbonyloxymethyl)-3-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate

Chemical Property:

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Technology Process of N-[4-(daunorubicin-N-carbonyloxymethyl)-3-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate

There total 7 articles about N-[4-(daunorubicin-N-carbonyloxymethyl)-3-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate 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:

methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate (72692-06-9,73464-50-3,3082-95-9) → N-[4-(daunorubicin-N-carbonyloxymethyl)-3-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate (247075-44-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / Et₃N / toluene / 0.5 h / 20 °C

2: NBS; AIBN / CCl₄ / 1 h / Heating; irradiation

3: 206 mg / AgNO₃; water / acetone / 48 h

4: i-Pr₂NEt / CH₂Cl₂ / 1.5 h

5: 56 mg / i-Pr₂NEt / CH₂Cl₂; dimethylformamide

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); water; silver nitrate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1: Addition / 2: Bromination / 3: Hydrolysis / 4: Esterification / 5: Acylation;

DOI:10.1016/S0968-0896(99)00095-4

Reference yield:

2-bromo-4-methyl-aniline; hydrochloride (13194-71-3) → N-[4-(daunorubicin-N-carbonyloxymethyl)-3-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate (247075-44-1)

Guidance literature:

Multi-step reaction with 6 steps

1: toluene / 2 h / Heating

2: 95 percent / Et₃N / toluene / 0.5 h / 20 °C

3: NBS; AIBN / CCl₄ / 1 h / Heating; irradiation

4: 206 mg / AgNO₃; water / acetone / 48 h

5: i-Pr₂NEt / CH₂Cl₂ / 1.5 h

6: 56 mg / i-Pr₂NEt / CH₂Cl₂; dimethylformamide

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); water; silver nitrate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1: Carbonylation / 2: Addition / 3: Bromination / 4: Hydrolysis / 5: Esterification / 6: Acylation;

DOI:10.1016/S0968-0896(99)00095-4

Reference yield:

2-Bromo-1-isocyanato-4-methyl-benzene (71189-13-4) → N-[4-(daunorubicin-N-carbonyloxymethyl)-3-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate (247075-44-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / Et₃N / toluene / 0.5 h / 20 °C

2: NBS; AIBN / CCl₄ / 1 h / Heating; irradiation

3: 206 mg / AgNO₃; water / acetone / 48 h

4: i-Pr₂NEt / CH₂Cl₂ / 1.5 h

5: 56 mg / i-Pr₂NEt / CH₂Cl₂; dimethylformamide

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); water; silver nitrate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1: Addition / 2: Bromination / 3: Hydrolysis / 4: Esterification / 5: Acylation;

DOI:10.1016/S0968-0896(99)00095-4

upstream raw materials:

daunomycin hydrochloride

methyl 2,3,4-tri-O-acetyl-D-glucopyranuronate

2-bromo-4-methyl-aniline; hydrochloride

2-Bromo-1-isocyanato-4-methyl-benzene

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