(7S,9S)-7,8,9,10-tetrahydro-6,7,9,11-tetrahydroxy-9-<<(phenylcarbamoyl)oxy>methyl>-5,12-naphthacenedione

Base Information

Chemical Name:(7S,9S)-7,8,9,10-tetrahydro-6,7,9,11-tetrahydroxy-9-<<(phenylcarbamoyl)oxy>methyl>-5,12-naphthacenedione
CAS No.:91593-21-4
Molecular Formula:C₂₆H₂₁NO₈
Molecular Weight:475.455
Hs Code.:

Synonyms:(7S,9S)-7,8,9,10-tetrahydro-6,7,9,11-tetrahydroxy-9-<<(phenylcarbamoyl)oxy>methyl>-5,12-naphthacenedione

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Chemical Property of (7S,9S)-7,8,9,10-tetrahydro-6,7,9,11-tetrahydroxy-9-<<(phenylcarbamoyl)oxy>methyl>-5,12-naphthacenedione

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Technology Process of (7S,9S)-7,8,9,10-tetrahydro-6,7,9,11-tetrahydroxy-9-<<(phenylcarbamoyl)oxy>methyl>-5,12-naphthacenedione

There total 7 articles about (7S,9S)-7,8,9,10-tetrahydro-6,7,9,11-tetrahydroxy-9-<<(phenylcarbamoyl)oxy>methyl>-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: 52.0%

: 103-71-9
phenyl isocyanate

: (2S,4S)-(+)-2,4,5,12-tetrahydroxy-2-hydroxymethyl-1,2,3,4-tetrahydronaphthacene-6,11-dione

: 91593-21-4
(7S,9S)-7,8,9,10-tetrahydro-6,7,9,11-tetrahydroxy-9-<<(phenylcarbamoyl)oxy>methyl>-5,12-naphthacenedione

Guidance literature:: In pyridine; for 10h; Ambient temperature;
DOI:10.1248/cpb.35.3658

Reference yield:

: 90146-19-3
(2R)-methyl 1,2,3,4,6,11-hexahydro-2,5,12-trihydroxy-6,11-dioxonaphthacene-2-carboxylate

: 91593-21-4
(7S,9S)-7,8,9,10-tetrahydro-6,7,9,11-tetrahydroxy-9-<<(phenylcarbamoyl)oxy>methyl>-5,12-naphthacenedione

Guidance literature:: Multi-step reaction with 5 steps

1: lithium tri-tert-butoxyaluminum hydride / dimethylsulfoxide / 10 h / Ambient temperature

2: 171 mg / p-toluenesulfonic acic (TSA) / dimethylformamide; tetrahydrofuran / 0.17 h / Ambient temperature

3: 1.) bromine; 2.) NaOH (0.3M) / 1.) carbon tetrachloride, 3.5 h, irradiation; 2.) 15 min

4: 100 percent / hydrogen fluoride / acetonitrile; H₂O / 0.5 h / Ambient temperature

5: 52 percent / pyridine / 10 h / Ambient temperature

With sodium hydroxide; lithium tri(t-butoxy)aluminum hydride; hydrogen fluoride; bromine; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1248/cpb.35.3658

Reference yield:

: 107022-83-3
(R)-2-(tert-butyldimethylsilyloxymethyl)-2,5,12-trihydroxy-1,2,3,4-tetrahydronaphthacene-6,11-dione

: 91593-21-4
(7S,9S)-7,8,9,10-tetrahydro-6,7,9,11-tetrahydroxy-9-<<(phenylcarbamoyl)oxy>methyl>-5,12-naphthacenedione

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) bromine; 2.) NaOH (0.3M) / 1.) carbon tetrachloride, 3.5 h, irradiation; 2.) 15 min

2: 100 percent / hydrogen fluoride / acetonitrile; H₂O / 0.5 h / Ambient temperature

3: 52 percent / pyridine / 10 h / Ambient temperature

With sodium hydroxide; hydrogen fluoride; bromine; In pyridine; water; acetonitrile;
DOI:10.1248/cpb.35.3658