(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

Base Information

• Chemical Name: (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
• CAS No.: 62414-03-3
• Molecular Formula: C₂₆H₂₇NO₉
• Molecular Weight: 497.502
• Mol file: 62414-03-3.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 4 articles about (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 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:

N-[(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)-3-hydroxy-2-methyl-tetrahydro-pyran-4-yl]-2,2,2-trifluoro-acetamide (62414-07-7) → (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 (62414-03-3,58957-91-8,58957-93-0)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; for 1h;

DOI:10.1021/jm00171a010

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)-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 (62414-03-3,58957-91-8,58957-93-0)

Guidance literature:

Multi-step reaction with 3 steps

1: silver trifluoromethanesulfonate / tetrahydrofuran; diethyl ether / 3.5 h / -5 °C

2: 0.1 M aq. NaOH / CH₂Cl₂; methanol / 0.5 h / 0 °C

3: 0.1 M aq. NaOH / tetrahydrofuran / 1 h

With sodium hydroxide; silver trifluoromethanesulfonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/jm00171a010

Reference yield:

(7S,9S)-idarubicinone (60660-75-5) → (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 (62414-03-3,58957-91-8,58957-93-0)

Guidance literature:

Multi-step reaction with 3 steps

1: silver trifluoromethanesulfonate / tetrahydrofuran; diethyl ether / 3.5 h / -5 °C

2: 0.1 M aq. NaOH / CH₂Cl₂; methanol / 0.5 h / 0 °C

3: 0.1 M aq. NaOH / tetrahydrofuran / 1 h

With sodium hydroxide; silver trifluoromethanesulfonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/jm00171a010

upstream raw materials:

N-[(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)-3-hydroxy-2-methyl-tetrahydro-pyran-4-yl]-2,2,2-trifluoro-acetamide

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

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