6β-<3-(benzyloxy)prop-1-yl>-1α-<(methoxymethyl)oxy>-1,2,3,4,6,8aα-hexahydronaphthalene-5-carboxylic acid

Base Information

Chemical Name:6β-<3-(benzyloxy)prop-1-yl>-1α-<(methoxymethyl)oxy>-1,2,3,4,6,8aα-hexahydronaphthalene-5-carboxylic acid
CAS No.:83220-58-0
Molecular Formula:C₂₃H₃₀O₅
Molecular Weight:386.488
Hs Code.:

Synonyms:6β-<3-(benzyloxy)prop-1-yl>-1α-<(methoxymethyl)oxy>-1,2,3,4,6,8aα-hexahydronaphthalene-5-carboxylic acid

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Chemical Property of 6β-<3-(benzyloxy)prop-1-yl>-1α-<(methoxymethyl)oxy>-1,2,3,4,6,8aα-hexahydronaphthalene-5-carboxylic acid

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Technology Process of 6β-<3-(benzyloxy)prop-1-yl>-1α-<(methoxymethyl)oxy>-1,2,3,4,6,8aα-hexahydronaphthalene-5-carboxylic acid

There total 7 articles about 6β-<3-(benzyloxy)prop-1-yl>-1α-<(methoxymethyl)oxy>-1,2,3,4,6,8aα-hexahydronaphthalene-5-carboxylic acid 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: 96.0%

: 83220-57-9
2,2,2-trichloroethyl 6β-<3-(benzyloxy)prop-1-yl>-1α-<(methoxymethyl)oxy>-1,2,3,4,6,8aα-hexahydronaphthalene-5-carboxylate

: 83220-58-0
6β-<3-(benzyloxy)prop-1-yl>-1α-<(methoxymethyl)oxy>-1,2,3,4,6,8aα-hexahydronaphthalene-5-carboxylic acid

Guidance literature:: With zinc; In methanol; for 2h; Heating;
DOI:10.1021/jo00145a002

Reference yield:

: 83220-50-2
(E,E)-8-(benzyloxy)-2,4-octadienal

: 83220-58-0
6β-<3-(benzyloxy)prop-1-yl>-1α-<(methoxymethyl)oxy>-1,2,3,4,6,8aα-hexahydronaphthalene-5-carboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

1: tetrahydrofuran / 0.5 h / 0 - 23 °C

2: KF / dimethylformamide; H₂O / 39 h / 23 °C

3: 98 percent Chromat_. / imidazole / tetrahydrofuran / 53 h / 23 °C

4: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) from -78 deg C to 0 deg C, 55 min

5: 61 percent / 2.) aq HCl / 1.) toluene, 160 deg C, 61 h, 2.) THF, MeOH, 10 deg C, 3.) 23 deg C, 10 h

6: EtN-i-Pr₂ / CH₂Cl₂ / 15 h / 23 °C

7: 96 percent / Zn / methanol / 2 h / Heating

With 1H-imidazole; hydrogenchloride; potassium fluoride; n-butyllithium; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo00145a002

Reference yield:

: 83220-51-3
(E,E)-1-(benzyloxy)-8-hydroxy-4,6-tridecadien-12-yne

: 83220-58-0
6β-<3-(benzyloxy)prop-1-yl>-1α-<(methoxymethyl)oxy>-1,2,3,4,6,8aα-hexahydronaphthalene-5-carboxylic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent Chromat_. / imidazole / tetrahydrofuran / 53 h / 23 °C

2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) from -78 deg C to 0 deg C, 55 min

3: 61 percent / 2.) aq HCl / 1.) toluene, 160 deg C, 61 h, 2.) THF, MeOH, 10 deg C, 3.) 23 deg C, 10 h

4: EtN-i-Pr₂ / CH₂Cl₂ / 15 h / 23 °C

5: 96 percent / Zn / methanol / 2 h / Heating

With 1H-imidazole; hydrogenchloride; n-butyllithium; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo00145a002