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

Base Information

• Chemical Name: 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
• CAS No.: 130767-72-5
• Molecular Formula: C₄₁H₄₅NO₁₄
• Molecular Weight: 775.807

Synonyms:

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 4 articles about 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 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:

C43H44F3NO15 (130767-71-4) → 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:

With sodium hydroxide; sodium chloride; In chloroform; for 2h; Yield given; Ambient temperature;

DOI:10.1246/cl.1990.1431

Reference yield:

3'-N-trifluoroacetyldaunorubicin (26388-52-3,52471-41-7,64686-33-5) → 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 3 steps

1: 62 percent / NBS / acetonitrile / 4 h / 0 °C

2: 49 percent / n-Bu₃SnH, AIBN / benzene / 28 h / 60 °C

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

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

DOI:10.1246/cl.1990.1431

Reference yield:

Benzoic acid (2R,3R,4S)-4-hydroxy-2,4-dimethyl-3,4-dihydro-2H-pyran-3-yl ester (115957-13-6,130854-99-8) → 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 3 steps

1: 62 percent / NBS / acetonitrile / 4 h / 0 °C

2: 49 percent / n-Bu₃SnH, AIBN / benzene / 28 h / 60 °C

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

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

DOI:10.1246/cl.1990.1431

upstream raw materials:

C₄₃H₄₄F₃NO₁₅

3'-N-trifluoroacetyldaunorubicin

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

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

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