(2S,2′R,4S,4′S,5S,5′R)-5-allyl-4-((4-bromobenzyl)oxy)-5′-ethyl-4′-((4-methoxybenzyl)oxy)octahydro-2,2′-bifuran

Base Information

Chemical Name:(2S,2′R,4S,4′S,5S,5′R)-5-allyl-4-((4-bromobenzyl)oxy)-5′-ethyl-4′-((4-methoxybenzyl)oxy)octahydro-2,2′-bifuran
CAS No.:1384514-24-2
Molecular Formula:C₂₈H₃₅BrO₅
Molecular Weight:531.487
Hs Code.:

Synonyms:(2S,2′R,4S,4′S,5S,5′R)-5-allyl-4-((4-bromobenzyl)oxy)-5′-ethyl-4′-((4-methoxybenzyl)oxy)octahydro-2,2′-bifuran

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Chemical Property of (2S,2′R,4S,4′S,5S,5′R)-5-allyl-4-((4-bromobenzyl)oxy)-5′-ethyl-4′-((4-methoxybenzyl)oxy)octahydro-2,2′-bifuran

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Technology Process of (2S,2′R,4S,4′S,5S,5′R)-5-allyl-4-((4-bromobenzyl)oxy)-5′-ethyl-4′-((4-methoxybenzyl)oxy)octahydro-2,2′-bifuran

There total 9 articles about (2S,2′R,4S,4′S,5S,5′R)-5-allyl-4-((4-bromobenzyl)oxy)-5′-ethyl-4′-((4-methoxybenzyl)oxy)octahydro-2,2′-bifuran 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: 58.0%

: 1384514-23-1
(2S,2'R,4S,4'S,5R,5'R)-4-(4-bromobenzyloxy)-5'-ethyl-5-(iodomethyl)-4'-(4-methoxybenzyloxy)octahydro-2,2'-bifuran

: 1826-67-1
vinyl magnesium bromide

: 1384514-24-2
(2S,2′R,4S,4′S,5S,5′R)-5-allyl-4-((4-bromobenzyl)oxy)-5′-ethyl-4′-((4-methoxybenzyl)oxy)octahydro-2,2′-bifuran

Guidance literature:: In tetrahydrofuran; benzene; at 40 ℃; for 4h; Inert atmosphere;
DOI:10.1021/ja304554e

Reference yield:

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

: 1384514-24-2
(2S,2′R,4S,4′S,5S,5′R)-5-allyl-4-((4-bromobenzyl)oxy)-5′-ethyl-4′-((4-methoxybenzyl)oxy)octahydro-2,2′-bifuran

Guidance literature:: Multi-step reaction with 10 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: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.33 h / 20 °C / Inert atmosphere

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

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

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

Reference yield:

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

: 1384514-24-2
(2S,2′R,4S,4′S,5S,5′R)-5-allyl-4-((4-bromobenzyl)oxy)-5′-ethyl-4′-((4-methoxybenzyl)oxy)octahydro-2,2′-bifuran

Guidance literature:: Multi-step reaction with 8 steps

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

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

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

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

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

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

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

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

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