(4aR,5R,8aR)-5-Benzyloxymethyl-1,1,6-trimethyl-4-oxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carboxylic acid methyl ester

Base Information

Chemical Name:(4aR,5R,8aR)-5-Benzyloxymethyl-1,1,6-trimethyl-4-oxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carboxylic acid methyl ester
CAS No.:123502-31-8
Molecular Formula:C₂₃H₂₈O₄
Molecular Weight:368.473
Hs Code.:

Synonyms:(4aR,5R,8aR)-5-Benzyloxymethyl-1,1,6-trimethyl-4-oxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carboxylic acid methyl ester

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Chemical Property of (4aR,5R,8aR)-5-Benzyloxymethyl-1,1,6-trimethyl-4-oxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carboxylic acid methyl ester

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Technology Process of (4aR,5R,8aR)-5-Benzyloxymethyl-1,1,6-trimethyl-4-oxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carboxylic acid methyl ester

There total 2 articles about (4aR,5R,8aR)-5-Benzyloxymethyl-1,1,6-trimethyl-4-oxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carboxylic acid methyl 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: 84.0%

: 65595-92-8
methyl 3,3-dimethyl-6-oxocyclohexa-1,4-dienecarboxylate

: 123502-30-7
(E)-3-methyl-5-benzyloxy-1,3-pentadiene

: 123502-31-8
(4aR,5R,8aR)-5-Benzyloxymethyl-1,1,6-trimethyl-4-oxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carboxylic acid methyl ester

Guidance literature:: iron(III) chloride; In diethyl ether; at -20 ℃; for 48h;
DOI:10.1016/S0040-4039(00)82438-7

Reference yield:

: 1572-08-3
(E)-3-methylpenta-2,4-dien-1-ol

: 123502-31-8
(4aR,5R,8aR)-5-Benzyloxymethyl-1,1,6-trimethyl-4-oxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent / NaH / tetrahydrofuran / 8 h / Ambient temperature

2: 84 percent / FeCl₃ / diethyl ether / 48 h / -20 °C

With sodium hydride; iron(III) chloride; In tetrahydrofuran; diethyl ether;
DOI:10.1016/S0040-4039(00)82438-7

Reference yield:

: 123502-31-8
(4aR,5R,8aR)-5-Benzyloxymethyl-1,1,6-trimethyl-4-oxo-1,5,8,8a-tetrahydro-4H-naphthalene-4a-carboxylic acid methyl ester

: 123502-37-4
(4aR,5R,8aR)-5-Benzyloxymethyl-4a-methoxymethoxymethyl-1,1,6-trimethyl-1,2,3,4,4a,5,8,8a-octahydro-naphthalene

Guidance literature:: Multi-step reaction with 6 steps

1: tris(triphenylphosphine)rhodium(I) chloride / benzene

2: n-Bu₄NF / tetrahydrofuran

3: 72 percent / sodium bis(2-methoxyethoxy)aluminum hydride / diethyl ether; toluene / Ambient temperature

4: 72 percent / KH / 1,2-dimethoxy-ethane / -10 °C

5: NaH / 1,2-dimethoxy-ethane / Ambient temperature

6: tri-n-butyltin hydride, AIBN / toluene / Heating

With 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; potassium hydride; sodium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; Wilkinson's catalyst; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; toluene; benzene;
DOI:10.1016/S0040-4039(00)82438-7