Methyl (4aS,5R,6S,8aS)-2,5,8a-trimethyl-6-(benzyloxy)-5-(benzyloxymethyl)-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

Base Information

Chemical Name:Methyl (4aS,5R,6S,8aS)-2,5,8a-trimethyl-6-(benzyloxy)-5-(benzyloxymethyl)-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate
CAS No.:171925-90-9
Molecular Formula:C₃₀H₃₈O₄
Molecular Weight:462.629
Hs Code.:

Synonyms:Methyl (4aS,5R,6S,8aS)-2,5,8a-trimethyl-6-(benzyloxy)-5-(benzyloxymethyl)-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

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Chemical Property of Methyl (4aS,5R,6S,8aS)-2,5,8a-trimethyl-6-(benzyloxy)-5-(benzyloxymethyl)-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

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Technology Process of Methyl (4aS,5R,6S,8aS)-2,5,8a-trimethyl-6-(benzyloxy)-5-(benzyloxymethyl)-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

There total 13 articles about Methyl (4aS,5R,6S,8aS)-2,5,8a-trimethyl-6-(benzyloxy)-5-(benzyloxymethyl)-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate 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: 72.0%

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 171925-89-6
Trifluoro-methanesulfonic acid (4aS,5R,6S,8aS)-6-benzyloxy-5-benzyloxymethyl-2,5,8a-trimethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl ester

: 171925-90-9
Methyl (4aS,5R,6S,8aS)-2,5,8a-trimethyl-6-(benzyloxy)-5-(benzyloxymethyl)-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

Guidance literature:: With palladium diacetate; triethylamine; triphenylphosphine; In N,N-dimethyl-formamide;
DOI:10.1021/jo00130a005

Reference yield: 51.0%

: 100-39-0
benzyl bromide

: 223907-24-2
Methyl (4aS,5R,6S,8aS)-6-hydroxy-5,8a-dimethyl-2-methylene-5-(benzyloxymethyl)perhydronaphthalene-1-carboxylate

: 171925-90-9
Methyl (4aS,5R,6S,8aS)-2,5,8a-trimethyl-6-(benzyloxy)-5-(benzyloxymethyl)-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

: 258528-50-6
(4aR,5R,6S,8aS)-6-Benzyloxy-5-benzyloxymethyl-5,8a-dimethyl-2-methylene-decahydro-naphthalene-1-carboxylic acid methyl ester

Guidance literature:: Methyl (4aS,5R,6S,8aS)-6-hydroxy-5,8a-dimethyl-2-methylene-5-(benzyloxymethyl)perhydronaphthalene-1-carboxylate; With sodium hydride; In tetrahydrofuran; for 4h; Heating;

benzyl bromide; In tetrahydrofuran; for 2h; Heating;
DOI:10.1039/a906589j

Reference yield:

: 389103-83-7
(4a'R,5'R,8a'S)-5'-(hydroxymethyl)-5',8a'-dimethylhexahydro-2'H-spiro[[1,3]dioxolane-2,1'-naphthalen]-6'(7'H)-one

: 171925-90-9
Methyl (4aS,5R,6S,8aS)-2,5,8a-trimethyl-6-(benzyloxy)-5-(benzyloxymethyl)-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / Me₄NBH(OAc)3, AcOH / acetonitrile

2: NaH / tetrahydrofuran

3: 2 N HCl / tetrahydrofuran

4: 1.) KDA, TMSCl, Et₃N, 2.) BTAF, 4 Angstroem MS / 1.) THF, 2.) THF

5: 86 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / Heating

6: 72 percent / Pd(OAc)2, PPh₃, Et₃N / dimethylformamide

With hydrogenchloride; palladium diacetate; chloro-trimethyl-silane; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem MS; Diethoxy-methyl-(6-amino-hexylaminomethyl)-silan; sodium hydride; acetic acid; triethylamine; triphenylphosphine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00130a005