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

Base Information

• Chemical Name: (2S,2'R,4S,4'S,5R,5'R)-4-(4-bromobenzyloxy)-5'-ethyl-5-(iodomethyl)-4'-(4-methoxybenzyloxy)octahydro-2,2'-bifuran
• CAS No.: 1384514-23-1
• Molecular Formula: C₂₆H₃₂BrIO₅
• Molecular Weight: 631.346

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

Chemical Property of (2S,2'R,4S,4'S,5R,5'R)-4-(4-bromobenzyloxy)-5'-ethyl-5-(iodomethyl)-4'-(4-methoxybenzyloxy)octahydro-2,2'-bifuran

Chemical Property:

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Technology Process of (2S,2'R,4S,4'S,5R,5'R)-4-(4-bromobenzyloxy)-5'-ethyl-5-(iodomethyl)-4'-(4-methoxybenzyloxy)octahydro-2,2'-bifuran

There total 8 articles about (2S,2'R,4S,4'S,5R,5'R)-4-(4-bromobenzyloxy)-5'-ethyl-5-(iodomethyl)-4'-(4-methoxybenzyloxy)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: 83.0%

((2S,2'R,4S,4'S,5S,5'R)-4-(4-bromobenzyloxy)-5'-ethyl-4'-(4-methoxybenzyloxy)octahydro-[2,2'-bifuran]-5-yl)methyl methanesulfonate (1384514-19-5) → (2S,2'R,4S,4'S,5R,5'R)-4-(4-bromobenzyloxy)-5'-ethyl-5-(iodomethyl)-4'-(4-methoxybenzyloxy)octahydro-2,2'-bifuran (1384514-23-1)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; In toluene; at 110 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ja304554e

Reference yield:

(3R,4S)-4-(4-methoxybenzyloxy)hept-6-en-3-ol (1384514-49-1) → (2S,2'R,4S,4'S,5R,5'R)-4-(4-bromobenzyloxy)-5'-ethyl-5-(iodomethyl)-4'-(4-methoxybenzyloxy)octahydro-2,2'-bifuran (1384514-23-1)

Guidance literature:

Multi-step reaction with 7 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

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;

DOI:10.1021/ja304554e

Reference yield:

triethyl (((3R,4S)-4-(4-methoxybenzyloxy)hept-6-en-3-yl)oxy)silane (1384514-14-0) → (2S,2'R,4S,4'S,5R,5'R)-4-(4-bromobenzyloxy)-5'-ethyl-5-(iodomethyl)-4'-(4-methoxybenzyloxy)octahydro-2,2'-bifuran (1384514-23-1)

Guidance literature:

Multi-step reaction with 6 steps

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

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

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

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

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

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

With 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;

DOI:10.1021/ja304554e

upstream raw materials:

(2R,3S)-1,2-epoxy-3-hydroxy-5-hexene

(3R,4S)-4-(4-methoxybenzyloxy)hept-6-en-3-ol

triethyl (((3R,4S)-4-(4-methoxybenzyloxy)hept-6-en-3-yl)oxy)silane

(1S,3S,4S,6S,7R)-1-(4-bromobenzyloxy)-6-(4-methoxybenzyloxy)-1-((R)-oxiran-2-yl)-7-(triethylsilyloxy)nonane-3,4-diol

Downstream raw materials:

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

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

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

(2R,2'S,4S,4'R,5R,5'S)-4,4'-dibromo-5-ethyl-5'-((Z)-pent-2-en-4-yn-1-yl)octahydro-2,2'-bifuran

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