N-[4-(daunorubicin-N-carbonyloxymethyl)phenyl] O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) carbamate

Base Information

• Chemical Name: N-[4-(daunorubicin-N-carbonyloxymethyl)phenyl] O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) carbamate
• CAS No.: 186653-78-1
• Molecular Formula: C₅₀H₅₄N₂O₂₃
• Molecular Weight: 1050.98
• Mol file: 186653-78-1.mol

Synonyms:N-[4-(daunorubicin-N-carbonyloxymethyl)phenyl] O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) carbamate

Chemical Property of N-[4-(daunorubicin-N-carbonyloxymethyl)phenyl] O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[4-(daunorubicin-N-carbonyloxymethyl)phenyl] O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) carbamate

There total 6 articles about N-[4-(daunorubicin-N-carbonyloxymethyl)phenyl] O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) 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:

2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose (3947-62-4,6207-76-7,10343-06-3,19235-21-3,22554-70-7,22860-22-6,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,47339-09-3) → N-[4-(daunorubicin-N-carbonyloxymethyl)phenyl] O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) carbamate (186653-78-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 57 percent / toluene / 20 °C

2: 100 percent / AcOH; H₂O / tetrahydrofuran / 3 h

3: i-Pr₂NEt / CH₂Cl₂ / 1.5 h

4: 171 mg / i-Pr₂NEt / CH₂Cl₂; dimethylformamide

With water; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Addition / 2: Hydrolysis / 3: Esterification / 4: Acylation;

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

Reference yield:

4-<(tert-butyldimethylsiloxy)methyl>benzoic acid (104292-83-3) → N-[4-(daunorubicin-N-carbonyloxymethyl)phenyl] O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) carbamate (186653-78-1)

Guidance literature:

Multi-step reaction with 5 steps

1: toluene / 3 h / 80 °C

2: 57 percent / toluene / 20 °C

3: 100 percent / AcOH; H₂O / tetrahydrofuran / 3 h

4: i-Pr₂NEt / CH₂Cl₂ / 1.5 h

5: 171 mg / i-Pr₂NEt / CH₂Cl₂; dimethylformamide

With water; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Curtius rearrangement / 2: Addition / 3: Hydrolysis / 4: Esterification / 5: Acylation;

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

Reference yield:

tert-butyl[(4-isocyanatophenyl)methoxy]dimethylsilane (922173-23-7) → N-[4-(daunorubicin-N-carbonyloxymethyl)phenyl] O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) carbamate (186653-78-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 57 percent / toluene / 20 °C

2: 100 percent / AcOH; H₂O / tetrahydrofuran / 3 h

3: i-Pr₂NEt / CH₂Cl₂ / 1.5 h

4: 171 mg / i-Pr₂NEt / CH₂Cl₂; dimethylformamide

With water; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Addition / 2: Hydrolysis / 3: Esterification / 4: Acylation;

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

upstream raw materials:

daunomycin hydrochloride

2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose

4-<(tert-butyldimethylsiloxy)methyl>benzoic acid

tert-butyl[(4-isocyanatophenyl)methoxy]dimethylsilane

Downstream raw materials:

N-[4-(daunorubicin-N-carbonyloxymethyl)phenyl] O-β-D-galactopyranosyl carbamate