2-[(1R,2S,5R)-1-((R)-4-Benzyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2-isopropyl-5-methyl-cyclohexyl]-1-phenyl-ethanone

Base Information

Chemical Name:2-[(1R,2S,5R)-1-((R)-4-Benzyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2-isopropyl-5-methyl-cyclohexyl]-1-phenyl-ethanone
CAS No.:138489-64-2
Molecular Formula:C₃₁H₄₂O₄
Molecular Weight:478.672
Hs Code.:

Synonyms:2-[(1R,2S,5R)-1-((R)-4-Benzyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2-isopropyl-5-methyl-cyclohexyl]-1-phenyl-ethanone

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Chemical Property of 2-[(1R,2S,5R)-1-((R)-4-Benzyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2-isopropyl-5-methyl-cyclohexyl]-1-phenyl-ethanone

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Technology Process of 2-[(1R,2S,5R)-1-((R)-4-Benzyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2-isopropyl-5-methyl-cyclohexyl]-1-phenyl-ethanone

There total 7 articles about 2-[(1R,2S,5R)-1-((R)-4-Benzyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2-isopropyl-5-methyl-cyclohexyl]-1-phenyl-ethanone 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:

: 105857-49-6
(7S,10R)-7-Isopropyl-10-methyl-3-methylene-1,5-dioxa-spiro[5.5]undecane

: 138489-64-2
2-[(1R,2S,5R)-1-((R)-4-Benzyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2-isopropyl-5-methyl-cyclohexyl]-1-phenyl-ethanone

Guidance literature:: Multi-step reaction with 6 steps

1: 65 percent / N-bromosuccinimide (NBS), pH 7.5 phosphate buffer / 2-methyl-propan-2-ol; H₂O / 5 h / 25 °C

2: 92 percent / t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 25 °C

3: 1.) CuCN / 1.) THF, cyclohexane, ether, -85 to -25 deg C, 2.5 h, 2.) THF, 25 deg C, 2 h

4: 84 percent / trimethylsilyl trifluoromethanesulfonate (TMSOTf) / tetrahydrofuran / 5 h / 25 °C

5: 1.) TiCl₄, 2.) aq. NaHCO₃ / 1.) CH₂Cl₂, -85 deg C, 1 h, 2.) MeOH, 5-10 h, rt

6: 10-camphoricsulfonic acid (CSA) / 0.5 h / 25 °C

With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; pH 7.5 phosphate buffer; (1S)-10-camphorsulfonic acid; potassium tert-butylate; titanium tetrachloride; sodium hydrogencarbonate; In tetrahydrofuran; water; tert-butyl alcohol;
DOI:10.1021/jo00028a057

Reference yield:

: 138489-56-2
(7S,10R)-3-Bromomethyl-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undecan-3-ol

: 138489-64-2
2-[(1R,2S,5R)-1-((R)-4-Benzyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2-isopropyl-5-methyl-cyclohexyl]-1-phenyl-ethanone

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / t-BuOK / 2-methyl-propan-2-ol / 0.5 h / 25 °C

2: 1.) CuCN / 1.) THF, cyclohexane, ether, -85 to -25 deg C, 2.5 h, 2.) THF, 25 deg C, 2 h

3: 84 percent / trimethylsilyl trifluoromethanesulfonate (TMSOTf) / tetrahydrofuran / 5 h / 25 °C

4: 1.) TiCl₄, 2.) aq. NaHCO₃ / 1.) CH₂Cl₂, -85 deg C, 1 h, 2.) MeOH, 5-10 h, rt

5: 10-camphoricsulfonic acid (CSA) / 0.5 h / 25 °C

With trimethylsilyl trifluoromethanesulfonate; (1S)-10-camphorsulfonic acid; potassium tert-butylate; titanium tetrachloride; sodium hydrogencarbonate; In tetrahydrofuran; tert-butyl alcohol;
DOI:10.1021/jo00028a057

Reference yield:

: 138489-47-1
(7S,10R)-3-Benzyl-7-isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undecan-3-ol

: 138489-64-2
2-[(1R,2S,5R)-1-((R)-4-Benzyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-2-isopropyl-5-methyl-cyclohexyl]-1-phenyl-ethanone

Guidance literature:: Multi-step reaction with 3 steps

1: 84 percent / trimethylsilyl trifluoromethanesulfonate (TMSOTf) / tetrahydrofuran / 5 h / 25 °C

2: 1.) TiCl₄, 2.) aq. NaHCO₃ / 1.) CH₂Cl₂, -85 deg C, 1 h, 2.) MeOH, 5-10 h, rt

3: 10-camphoricsulfonic acid (CSA) / 0.5 h / 25 °C

With trimethylsilyl trifluoromethanesulfonate; (1S)-10-camphorsulfonic acid; titanium tetrachloride; sodium hydrogencarbonate; In tetrahydrofuran;
DOI:10.1021/jo00028a057