((2S,3S,5R)-3-(4-bromobenzyloxy)-5-((1R,3S,4R)-1-hydroxy-3-(4-methoxybenzyloxy)-4-(triethylsilyloxy)hexyl)tetrahydrofuran-2-yl)methyl methanesulfonate

Base Information

Chemical Name:((2S,3S,5R)-3-(4-bromobenzyloxy)-5-((1R,3S,4R)-1-hydroxy-3-(4-methoxybenzyloxy)-4-(triethylsilyloxy)hexyl)tetrahydrofuran-2-yl)methyl methanesulfonate
CAS No.:1384514-54-8
Molecular Formula:C₃₃H₅₁BrO₉SSi
Molecular Weight:731.818
Hs Code.:

((2S,3S,5R)-3-(4-bromobenzyloxy)-5-((1R,3S,4R)-1-hydroxy-3-(4-methoxybenzyloxy)-4-(triethylsilyloxy)hexyl)tetrahydrofuran-2-yl)methyl methanesulfonate

Synonyms:((2S,3S,5R)-3-(4-bromobenzyloxy)-5-((1R,3S,4R)-1-hydroxy-3-(4-methoxybenzyloxy)-4-(triethylsilyloxy)hexyl)tetrahydrofuran-2-yl)methyl methanesulfonate

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Chemical Property of ((2S,3S,5R)-3-(4-bromobenzyloxy)-5-((1R,3S,4R)-1-hydroxy-3-(4-methoxybenzyloxy)-4-(triethylsilyloxy)hexyl)tetrahydrofuran-2-yl)methyl methanesulfonate

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Technology Process of ((2S,3S,5R)-3-(4-bromobenzyloxy)-5-((1R,3S,4R)-1-hydroxy-3-(4-methoxybenzyloxy)-4-(triethylsilyloxy)hexyl)tetrahydrofuran-2-yl)methyl methanesulfonate

There total 7 articles about ((2S,3S,5R)-3-(4-bromobenzyloxy)-5-((1R,3S,4R)-1-hydroxy-3-(4-methoxybenzyloxy)-4-(triethylsilyloxy)hexyl)tetrahydrofuran-2-yl)methyl methanesulfonate 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: 30.0%

: 1384514-52-6
(1R,3S,4R)-1-((2R,4S,5S)-4-(4-bromobenzyloxy)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3-(4-methoxybenzyloxy)-4-(triethylsilyloxy)hexan-1-ol

: 124-63-0
methanesulfonyl chloride

: 1384514-54-8
((2S,3S,5R)-3-(4-bromobenzyloxy)-5-((1R,3S,4R)-1-hydroxy-3-(4-methoxybenzyloxy)-4-(triethylsilyloxy)hexyl)tetrahydrofuran-2-yl)methyl methanesulfonate

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 0.166667h; Inert atmosphere;
DOI:10.1021/ja304554e

Reference yield:

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

: 1384514-54-8
((2S,3S,5R)-3-(4-bromobenzyloxy)-5-((1R,3S,4R)-1-hydroxy-3-(4-methoxybenzyloxy)-4-(triethylsilyloxy)hexyl)tetrahydrofuran-2-yl)methyl methanesulfonate

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

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

: 1384514-54-8
((2S,3S,5R)-3-(4-bromobenzyloxy)-5-((1R,3S,4R)-1-hydroxy-3-(4-methoxybenzyloxy)-4-(triethylsilyloxy)hexyl)tetrahydrofuran-2-yl)methyl methanesulfonate

Guidance literature:: Multi-step reaction with 5 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

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