10-[2-(2-benzyloxy-propyl)-[1,3]dioxolan-2-ylmethyl]-1,8,11-trihydroxy-3-methoxymethoxy-2-methyl-naphthacene-5,12-dione

Base Information

Chemical Name:10-[2-(2-benzyloxy-propyl)-[1,3]dioxolan-2-ylmethyl]-1,8,11-trihydroxy-3-methoxymethoxy-2-methyl-naphthacene-5,12-dione
CAS No.:500770-33-2
Molecular Formula:C₃₅H₃₄O₁₀
Molecular Weight:614.649
Hs Code.:

Synonyms:10-[2-(2-benzyloxy-propyl)-[1,3]dioxolan-2-ylmethyl]-1,8,11-trihydroxy-3-methoxymethoxy-2-methyl-naphthacene-5,12-dione

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Chemical Property of 10-[2-(2-benzyloxy-propyl)-[1,3]dioxolan-2-ylmethyl]-1,8,11-trihydroxy-3-methoxymethoxy-2-methyl-naphthacene-5,12-dione

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Technology Process of 10-[2-(2-benzyloxy-propyl)-[1,3]dioxolan-2-ylmethyl]-1,8,11-trihydroxy-3-methoxymethoxy-2-methyl-naphthacene-5,12-dione

There total 16 articles about 10-[2-(2-benzyloxy-propyl)-[1,3]dioxolan-2-ylmethyl]-1,8,11-trihydroxy-3-methoxymethoxy-2-methyl-naphthacene-5,12-dione 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: 85.0%

: 500770-32-1
phosphoric acid 4-[2-(2-benzyloxy-propyl)-[1,3]dioxolan-2-ylmethyl]-5,7-dihydroxy-9-methoxymethoxy-8-methyl-6,11-dioxo-6,11-dihydro-naphthacen-2-yl ester diethyl ester

: 500770-33-2
10-[2-(2-benzyloxy-propyl)-[1,3]dioxolan-2-ylmethyl]-1,8,11-trihydroxy-3-methoxymethoxy-2-methyl-naphthacene-5,12-dione

Guidance literature:: With potassium tert-butylate; In water; tert-butyl alcohol; at 60 ℃; for 0.25h;
DOI:10.7164/antibiotics.55.1076

Reference yield:

: 608-25-3
2-methylbenzene-1,3-diol

: 500770-33-2
10-[2-(2-benzyloxy-propyl)-[1,3]dioxolan-2-ylmethyl]-1,8,11-trihydroxy-3-methoxymethoxy-2-methyl-naphthacene-5,12-dione

Guidance literature:: Multi-step reaction with 6 steps

1.1: 87 percent / NaH / dimethylformamide / 0.5 h / 0 - 20 °C

2.1: 78 percent / s-BuLi / tetrahydrofuran / 0.5 h / -78 - 20 °C

3.1: 82 percent / s-BuLi; TMEDA / tetrahydrofuran / 0.5 h / -78 - 20 °C

4.1: AcOH / 16 h / 80 °C

4.2: i-Pr₂NEt / dimethylformamide / 0.5 h / -40 - 20 °C

5.1: LiN(TMS)2 / tetrahydrofuran / 2 h / -78 - 60 °C

5.2: 64 percent / BnOMe / Pd-C / toluene / 15 h / 110 °C

6.1: 85 percent / t-BuOK / H₂O; 2-methyl-propan-2-ol / 0.25 h / 60 °C

With N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate; sec.-butyllithium; sodium hydride; acetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.7164/antibiotics.55.1076

Reference yield:

: 221449-83-8
1,3-bis(methoxymethoxy)-2-methylbenzene

: 500770-33-2
10-[2-(2-benzyloxy-propyl)-[1,3]dioxolan-2-ylmethyl]-1,8,11-trihydroxy-3-methoxymethoxy-2-methyl-naphthacene-5,12-dione

Guidance literature:: Multi-step reaction with 5 steps

1.1: 78 percent / s-BuLi / tetrahydrofuran / 0.5 h / -78 - 20 °C

2.1: 82 percent / s-BuLi; TMEDA / tetrahydrofuran / 0.5 h / -78 - 20 °C

3.1: AcOH / 16 h / 80 °C

3.2: i-Pr₂NEt / dimethylformamide / 0.5 h / -40 - 20 °C

4.1: LiN(TMS)2 / tetrahydrofuran / 2 h / -78 - 60 °C

4.2: 64 percent / BnOMe / Pd-C / toluene / 15 h / 110 °C

5.1: 85 percent / t-BuOK / H₂O; 2-methyl-propan-2-ol / 0.25 h / 60 °C

With N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate; sec.-butyllithium; acetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; water; tert-butyl alcohol;
DOI:10.7164/antibiotics.55.1076