<1S<1α(S*),7β,8β,8aβ>>-2-methylbutanoic acid 8-benzyloxymethyl-1,2,3,7,8,8a-hexahydro-7-methyl-naphthalenyl ester

Base Information

Chemical Name:<1S<1α(S*),7β,8β,8aβ>>-2-methylbutanoic acid 8-benzyloxymethyl-1,2,3,7,8,8a-hexahydro-7-methyl-naphthalenyl ester
CAS No.:160062-74-8
Molecular Formula:C₂₄H₃₂O₃
Molecular Weight:368.516
Hs Code.:

Synonyms:<1S<1α(S*),7β,8β,8aβ>>-2-methylbutanoic acid 8-benzyloxymethyl-1,2,3,7,8,8a-hexahydro-7-methyl-naphthalenyl ester

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Chemical Property of <1S<1α(S*),7β,8β,8aβ>>-2-methylbutanoic acid 8-benzyloxymethyl-1,2,3,7,8,8a-hexahydro-7-methyl-naphthalenyl ester

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Technology Process of <1S<1α(S*),7β,8β,8aβ>>-2-methylbutanoic acid 8-benzyloxymethyl-1,2,3,7,8,8a-hexahydro-7-methyl-naphthalenyl ester

There total 17 articles about <1S<1α(S*),7β,8β,8aβ>>-2-methylbutanoic acid 8-benzyloxymethyl-1,2,3,7,8,8a-hexahydro-7-methyl-naphthalenyl 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: 68.0%

: 160062-73-7
<1S<1α(S*),5αβ,7β,8β,8aβ>>-2-methylbutanoic acid 8-benzyloxymethyl-5-hydroxy-7-methyl-1,2,3,5,6,7,8,8a-octahydro-1-naphthalenyl ester

: 160062-74-8
<1S<1α(S*),7β,8β,8aβ>>-2-methylbutanoic acid 8-benzyloxymethyl-1,2,3,7,8,8a-hexahydro-7-methyl-naphthalenyl ester

Guidance literature:: With methanesulfonyl chloride; In pyridine; for 4h;
DOI:10.1016/S0040-4020(01)85667-2

Reference yield:

: 62617-91-8
ethyl 2-methyl-4-oxocyclohexane-1-carboxylate

: 160062-74-8
<1S<1α(S*),7β,8β,8aβ>>-2-methylbutanoic acid 8-benzyloxymethyl-1,2,3,7,8,8a-hexahydro-7-methyl-naphthalenyl ester

Guidance literature:: Multi-step reaction with 15 steps

1: 1.) pig liver esterase / 1.) water, room t., pH=7; 2.) ether

2: 93 percent / p-toluenesulfonic acid / toluene / 2 h / Heating

3: 92 percent / LiAlH₄ / diethyl ether / 3 h / Ambient temperature

4: 90 percent / sodium hydride, tetrabutyl ammonium iodide / tetrahydrofuran / 24 h / Ambient temperature

5: 80 percent / 5percent HCl / tetrahydrofuran / 12 h / Ambient temperature

6: 1.) LDA, chlorotrimethylsilane; 2.) Pd(OAc)2, p-benzoquinone / 1.) THF, from -78 degC to room t. over 1 h; 2.) acetonitrile, room t., 6 h

7: 83 percent / potassium tert-butoxide / tetrahydrofuran / 36 h / Ambient temperature

8: 60.8 percent / HCl / ethanol / 2.5 h / Heating

9: 99.8 percent / CeCl₃*6H₂O, NaBH₄ / methanol / 0.17 h / Ambient temperature

10: 23 percent / hydrogen peroxide, potassium carbonate / methanol / 15 h / Ambient temperature

11: 80 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / Ambient temperature

12: 75 percent / lithium aluminum tri-tert-butoxide hydride / tetrahydrofuran / 6 h / Ambient temperature

13: 85 percent / dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / Ambient temperature

14: 68 percent / p-toluenesulfonic acid / tetrahydrofuran / 24 h / Ambient temperature

15: 68 percent / methansulfonyl chloride / pyridine / 4 h

With hydrogenchloride; dmap; palladium diacetate; sodium tetrahydroborate; lithium aluminium tetrahydride; chloro-trimethyl-silane; pig liver esterase; cerium(III) chloride; potassium tert-butylate; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; lithium tri-t-butoxyaluminum hydride; triethylamine; dicyclohexyl-carbodiimide; p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; toluene;
DOI:10.1016/S0040-4020(01)85667-2

Reference yield:

: 100-39-0
benzyl bromide

: 160062-74-8
<1S<1α(S*),7β,8β,8aβ>>-2-methylbutanoic acid 8-benzyloxymethyl-1,2,3,7,8,8a-hexahydro-7-methyl-naphthalenyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 90 percent / sodium hydride, tetrabutyl ammonium iodide / tetrahydrofuran / 24 h / Ambient temperature

2: 80 percent / 5percent HCl / tetrahydrofuran / 12 h / Ambient temperature

3: 1.) LDA, chlorotrimethylsilane; 2.) Pd(OAc)2, p-benzoquinone / 1.) THF, from -78 degC to room t. over 1 h; 2.) acetonitrile, room t., 6 h

4: 83 percent / potassium tert-butoxide / tetrahydrofuran / 36 h / Ambient temperature

5: 60.8 percent / HCl / ethanol / 2.5 h / Heating

6: 99.8 percent / CeCl₃*6H₂O, NaBH₄ / methanol / 0.17 h / Ambient temperature

7: 23 percent / hydrogen peroxide, potassium carbonate / methanol / 15 h / Ambient temperature

8: 80 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / Ambient temperature

9: 75 percent / lithium aluminum tri-tert-butoxide hydride / tetrahydrofuran / 6 h / Ambient temperature

10: 85 percent / dicyclohexylcarbodiimide, 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / Ambient temperature

11: 68 percent / p-toluenesulfonic acid / tetrahydrofuran / 24 h / Ambient temperature

12: 68 percent / methansulfonyl chloride / pyridine / 4 h

With hydrogenchloride; dmap; palladium diacetate; sodium tetrahydroborate; chloro-trimethyl-silane; cerium(III) chloride; potassium tert-butylate; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; lithium tri-t-butoxyaluminum hydride; triethylamine; dicyclohexyl-carbodiimide; p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane;
DOI:10.1016/S0040-4020(01)85667-2