(-)-4'-O-p-Nitrobenzoyl-N-trifluoroacetyl-4-demethoxydaunorubicin

Base Information

• Chemical Name: (-)-4'-O-p-Nitrobenzoyl-N-trifluoroacetyl-4-demethoxydaunorubicin
• CAS No.: 82343-11-1
• Molecular Formula: C₃₅H₂₉F₃N₂O₁₃
• Molecular Weight: 742.616
• Mol file: 82343-11-1.mol

Synonyms:

Chemical Property of (-)-4'-O-p-Nitrobenzoyl-N-trifluoroacetyl-4-demethoxydaunorubicin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-4'-O-p-Nitrobenzoyl-N-trifluoroacetyl-4-demethoxydaunorubicin

There total 5 articles about (-)-4'-O-p-Nitrobenzoyl-N-trifluoroacetyl-4-demethoxydaunorubicin 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: 84.0%

(7S,9S)-idarubicinone (60660-75-5) + 1-chloro-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxohexopyranose (63700-25-4) → (-)-4'-O-p-Nitrobenzoyl-N-trifluoroacetyl-4-demethoxydaunorubicin (82343-11-1,84276-23-3,103665-89-0)

Guidance literature:

silver trifluoromethanesulfonate;

DOI:10.1039/c39820000158

Reference yield:

4-Nitro-benzoic acid (2S,3R,4S)-6-chloro-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester (128572-89-4) + (7S,9S)-idarubicinone (60660-75-5) → 4-Nitro-benzoic acid (2S,3R,4S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester (82343-11-1,84276-23-3,103665-89-0)

Guidance literature:

With silver trifluoromethanesulfonate; In tetrahydrofuran; diethyl ether; at -5 ℃; for 3.5h;

DOI:10.1021/jm00171a010

Reference yield:

2,3,6-trideoxy-4-O-(p-nitrobenzoyl)-3-(trifluoroacetamido)-α-L-lyxo-hexopyranosyl p-nitrobenzoate (63700-24-3) → (-)-4'-O-p-Nitrobenzoyl-N-trifluoroacetyl-4-demethoxydaunorubicin (82343-11-1,84276-23-3,103665-89-0)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / CH₂Cl₂ / 0.17 h / Ambient temperature

2: silver trifluoromethanesulphonate / tetrahydrofuran; diethyl ether / 3.5 h / -3 °C

With hydrogenchloride; silver trifluoromethanesulfonate; In tetrahydrofuran; diethyl ether; dichloromethane;

upstream raw materials:

4-Nitro-benzoic acid (2S,3R,4S)-6-chloro-2-methyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester

(7S,9S)-idarubicinone

2,3,6-trideoxy-1,4-di-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxopyranose

1-chloro-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxohexopyranose

Downstream raw materials:

idarubicin

idarubicin hydrochloride

(+)-N-Trifluoroacetyl-4-demethoxydaunorubicin

(7S,9S)-9-acetyl-7-<(3'-amino-2',3',6'-trideoxy-α-L-arabinohexopyranosyl)oxy>-7,8,9,10-tetrahydro-6,9,11-trihydroxy-5,12-naphthacenedione