(2R,2'S,4R,4'S,5R,5'S)-5'-allyl-4'-(4-bromobenzyloxy)-5-ethyloctahydro-[2,2'-bifuran]-4-yl 4-nitrobenzoate

Base Information

Chemical Name:(2R,2'S,4R,4'S,5R,5'S)-5'-allyl-4'-(4-bromobenzyloxy)-5-ethyloctahydro-[2,2'-bifuran]-4-yl 4-nitrobenzoate
CAS No.:1384514-58-2
Molecular Formula:C₂₇H₃₀BrNO₇
Molecular Weight:560.442
Hs Code.:

Synonyms:(2R,2'S,4R,4'S,5R,5'S)-5'-allyl-4'-(4-bromobenzyloxy)-5-ethyloctahydro-[2,2'-bifuran]-4-yl 4-nitrobenzoate

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Chemical Property of (2R,2'S,4R,4'S,5R,5'S)-5'-allyl-4'-(4-bromobenzyloxy)-5-ethyloctahydro-[2,2'-bifuran]-4-yl 4-nitrobenzoate

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Technology Process of (2R,2'S,4R,4'S,5R,5'S)-5'-allyl-4'-(4-bromobenzyloxy)-5-ethyloctahydro-[2,2'-bifuran]-4-yl 4-nitrobenzoate

There total 12 articles about (2R,2'S,4R,4'S,5R,5'S)-5'-allyl-4'-(4-bromobenzyloxy)-5-ethyloctahydro-[2,2'-bifuran]-4-yl 4-nitrobenzoate 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: 85.0%

: 1384514-25-3
(2R,2'S,4S,4'S,5R,5'S)-5'-allyl-4'-(4-bromobenzyloxy)-5-ethyloctahydro-[2,2'-bifuran]-4-ol

: 62-23-7
4-nitro-benzoic acid

: 1384514-58-2
(2R,2'S,4R,4'S,5R,5'S)-5'-allyl-4'-(4-bromobenzyloxy)-5-ethyloctahydro-[2,2'-bifuran]-4-yl 4-nitrobenzoate

Guidance literature:: (2R,2'S,4S,4'S,5R,5'S)-5'-allyl-4'-(4-bromobenzyloxy)-5-ethyloctahydro-[2,2'-bifuran]-4-ol; With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

4-nitro-benzoic acid; In tetrahydrofuran; for 2h; Inert atmosphere;
DOI:10.1021/ja304554e

Reference yield:

: 936724-50-4
(2R,3S)-1,2-epoxy-3-hydroxy-5-hexene

: 1384514-58-2
(2R,2'S,4R,4'S,5R,5'S)-5'-allyl-4'-(4-bromobenzyloxy)-5-ethyloctahydro-[2,2'-bifuran]-4-yl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 11 steps

1.1: tetra-(n-butyl)ammonium iodide / tetrahydrofuran / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

1.3: 1 h / -23 °C / Inert atmosphere

2.1: 1H-imidazole; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere

3.1: Hoveyda-Grubbs catalyst second generation; p-benzoquinone / dichloromethane / 72 h / 40 °C / Inert atmosphere

4.1: potassium osmate(VI) dihydrate; methanesulfonamide; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 96 h / 0 °C

5.1: camphor-10-sulfonic acid / dichloromethane / 3 h / 0 °C / Inert atmosphere

6.1: triethylamine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

8.1: tetra-(n-butyl)ammonium iodide / toluene / 16 h / 110 °C / Inert atmosphere

9.1: tetrahydrofuran; benzene / 4 h / 40 °C / Inert atmosphere

10.1: boron trichloride - methyl sulfide complex / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

11.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

11.2: 2 h / Inert atmosphere

With 1H-imidazole; dmap; potassium osmate(VI) dihydrate; Hoveyda-Grubbs catalyst second generation; methanesulfonamide; di-isopropyl azodicarboxylate; boron trichloride - methyl sulfide complex; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; triphenylphosphine; p-benzoquinone; potassium hexacyanoferrate(III); In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol; benzene; 11.2: Mitsunobu reaction;
DOI:10.1021/ja304554e

Reference yield:

: 1384514-49-1
(3R,4S)-4-(4-methoxybenzyloxy)hept-6-en-3-ol

: 1384514-58-2
(2R,2'S,4R,4'S,5R,5'S)-5'-allyl-4'-(4-bromobenzyloxy)-5-ethyloctahydro-[2,2'-bifuran]-4-yl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 10 steps

1.1: 1H-imidazole; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: Hoveyda-Grubbs catalyst second generation; p-benzoquinone / dichloromethane / 72 h / 40 °C / Inert atmosphere

3.1: potassium osmate(VI) dihydrate; methanesulfonamide; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III) / water; tert-butyl alcohol / 96 h / 0 °C

4.1: camphor-10-sulfonic acid / dichloromethane / 3 h / 0 °C / Inert atmosphere

5.1: triethylamine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

7.1: tetra-(n-butyl)ammonium iodide / toluene / 16 h / 110 °C / Inert atmosphere

8.1: tetrahydrofuran; benzene / 4 h / 40 °C / Inert atmosphere

9.1: boron trichloride - methyl sulfide complex / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

10.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

10.2: 2 h / Inert atmosphere

With 1H-imidazole; dmap; potassium osmate(VI) dihydrate; Hoveyda-Grubbs catalyst second generation; methanesulfonamide; di-isopropyl azodicarboxylate; boron trichloride - methyl sulfide complex; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; triphenylphosphine; p-benzoquinone; potassium hexacyanoferrate(III); In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol; benzene; 10.2: Mitsunobu reaction;
DOI:10.1021/ja304554e