4'-O-(4-O-Benzoyl-2-bromo-2,6-dideoxy-3-C-methyl-α-D-altropyranosyl)-3'-N-trifluoroacetyldaunomycin

Base Information

• Chemical Name: 4'-O-(4-O-Benzoyl-2-bromo-2,6-dideoxy-3-C-methyl-α-D-altropyranosyl)-3'-N-trifluoroacetyldaunomycin
• CAS No.: 130767-70-3
• Molecular Formula: C₄₃H₄₃BrF₃NO₁₅
• Molecular Weight: 950.711
• Mol file: 130767-70-3.mol

Synonyms:4'-O-(4-O-Benzoyl-2-bromo-2,6-dideoxy-3-C-methyl-α-D-altropyranosyl)-3'-N-trifluoroacetyldaunomycin

Chemical Property of 4'-O-(4-O-Benzoyl-2-bromo-2,6-dideoxy-3-C-methyl-α-D-altropyranosyl)-3'-N-trifluoroacetyldaunomycin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4'-O-(4-O-Benzoyl-2-bromo-2,6-dideoxy-3-C-methyl-α-D-altropyranosyl)-3'-N-trifluoroacetyldaunomycin

There total 1 articles about 4'-O-(4-O-Benzoyl-2-bromo-2,6-dideoxy-3-C-methyl-α-D-altropyranosyl)-3'-N-trifluoroacetyldaunomycin 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: 62.0%

3'-N-trifluoroacetyldaunorubicin (26388-52-3,52471-41-7,64686-33-5) + Benzoic acid (2R,3R,4S)-4-hydroxy-2,4-dimethyl-3,4-dihydro-2H-pyran-3-yl ester (115957-13-6,130854-99-8) → 4'-O-(4-O-Benzoyl-2-bromo-2,6-dideoxy-3-C-methyl-α-D-altropyranosyl)-3'-N-trifluoroacetyldaunomycin (130767-70-3)

Guidance literature:

With N-Bromosuccinimide; In acetonitrile; at 0 ℃; for 4h;

DOI:10.1246/cl.1990.1431

Reference yield: 49.0%

4'-O-(4-O-Benzoyl-2-bromo-2,6-dideoxy-3-C-methyl-α-D-altropyranosyl)-3'-N-trifluoroacetyldaunomycin (130767-70-3) → C43H44F3NO15 (130767-71-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 60 ℃; for 28h;

DOI:10.1246/cl.1990.1431

Reference yield:

4'-O-(4-O-Benzoyl-2-bromo-2,6-dideoxy-3-C-methyl-α-D-altropyranosyl)-3'-N-trifluoroacetyldaunomycin (130767-70-3) → Benzoic acid (2R,3R,4S,6R)-6-[(2S,3S,4S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-4-amino-2-methyl-tetrahydro-pyran-3-yloxy]-4-hydroxy-2,4-dimethyl-tetrahydro-pyran-3-yl ester (130767-72-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 49 percent / n-Bu₃SnH, AIBN / benzene / 28 h / 60 °C

2: NaOH, saturated aq. NaCl / CHCl₃ / 2 h / Ambient temperature

With sodium hydroxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium chloride; In chloroform; benzene;

DOI:10.1246/cl.1990.1431

upstream raw materials:

3'-N-trifluoroacetyldaunorubicin

Benzoic acid (2R,3R,4S)-4-hydroxy-2,4-dimethyl-3,4-dihydro-2H-pyran-3-yl ester

Downstream raw materials:

C₄₃H₄₄F₃NO₁₅

Benzoic acid (2R,3R,4S,6R)-6-[(2S,3S,4S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-4-amino-2-methyl-tetrahydro-pyran-3-yloxy]-4-hydroxy-2,4-dimethyl-tetrahydro-pyran-3-yl ester