(4aS,5S,6R,7R,8aS)-6-Methoxy-7-(3,4,5-trimethoxy-benzoyloxy)-octahydro-isoquinoline-2,5-dicarboxylic acid dimethyl ester

Base Information

Chemical Name:(4aS,5S,6R,7R,8aS)-6-Methoxy-7-(3,4,5-trimethoxy-benzoyloxy)-octahydro-isoquinoline-2,5-dicarboxylic acid dimethyl ester
CAS No.:112547-24-7
Molecular Formula:C₂₄H₃₃NO₁₀
Molecular Weight:495.527
Hs Code.:

Synonyms:(4aS,5S,6R,7R,8aS)-6-Methoxy-7-(3,4,5-trimethoxy-benzoyloxy)-octahydro-isoquinoline-2,5-dicarboxylic acid dimethyl ester

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Chemical Property of (4aS,5S,6R,7R,8aS)-6-Methoxy-7-(3,4,5-trimethoxy-benzoyloxy)-octahydro-isoquinoline-2,5-dicarboxylic acid dimethyl ester

Chemical Property:

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Technology Process of (4aS,5S,6R,7R,8aS)-6-Methoxy-7-(3,4,5-trimethoxy-benzoyloxy)-octahydro-isoquinoline-2,5-dicarboxylic acid dimethyl ester

There total 1 articles about (4aS,5S,6R,7R,8aS)-6-Methoxy-7-(3,4,5-trimethoxy-benzoyloxy)-octahydro-isoquinoline-2,5-dicarboxylic acid dimethyl 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:

: 16625-53-9
2,3-secoreserpine

: 79-22-1
methyl chloroformate

: 112547-24-7
(4aS,5S,6R,7R,8aS)-6-Methoxy-7-(3,4,5-trimethoxy-benzoyloxy)-octahydro-isoquinoline-2,5-dicarboxylic acid dimethyl ester

Guidance literature:: In benzene; Heating;
DOI:10.1021/ja00539a038

Reference yield:

: 112547-24-7
(4aS,5S,6R,7R,8aS)-6-Methoxy-7-(3,4,5-trimethoxy-benzoyloxy)-octahydro-isoquinoline-2,5-dicarboxylic acid dimethyl ester

: 482-85-9
Isoreserpin

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) LiAlH₄, 2.) Et₃N, DMAP

2: 90 percent / (trimethylsilyl)iodide

3: 85 percent / K₂CO₃ / methanol / 25 h / Heating

4: 2.) NaBH₄

5: 53 percent

6: 62 percent / 0.3M KOH / methanol / 0.08 h / 25 °C

7: 65 percent / DCC, H₃PO₄ / dimethylsulfoxide

8: 1.) acetone cyanohydrin, 2.) oxalyl chloride

9: 85 percent / NaBH₄

With dmap; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; trimethylsilyl iodide; phosphoric acid; potassium carbonate; triethylamine; 2-hydroxy-2-methylpropanenitrile; dicyclohexyl-carbodiimide; In methanol; dimethyl sulfoxide;
DOI:10.1021/ja00539a038

Reference yield:

: 112547-24-7
(4aS,5S,6R,7R,8aS)-6-Methoxy-7-(3,4,5-trimethoxy-benzoyloxy)-octahydro-isoquinoline-2,5-dicarboxylic acid dimethyl ester

: 6242-28-0,75331-72-5
3,4,5-Trimethoxy-benzoic acid (1R,2R,3R,4aS,13bS,14aS)-1-hydroxymethyl-2,11-dimethoxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinolin-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) LiAlH₄, 2.) Et₃N, DMAP

2: 90 percent / (trimethylsilyl)iodide

3: 85 percent / K₂CO₃ / methanol / 25 h / Heating

4: 2.) NaBH₄

5: 53 percent

6: 62 percent / 0.3M KOH / methanol / 0.08 h / 25 °C

With dmap; potassium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; trimethylsilyl iodide; potassium carbonate; triethylamine; In methanol;
DOI:10.1021/ja00539a038