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

Base Information

• Chemical Name: (1S,3R,4R,6S,7R)-1-(4-bromobenzyloxy)-6-(4-methoxybenzyloxy)-1-((R)-oxiran-2-yl)-7-(triethylsilyloxy)nonane-3,4-diol
• CAS No.: 1384514-51-5
• Molecular Formula: C₃₂H₄₉BrO₇Si
• Molecular Weight: 653.726

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

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

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

There total 5 articles about (1S,3R,4R,6S,7R)-1-(4-bromobenzyloxy)-6-(4-methoxybenzyloxy)-1-((R)-oxiran-2-yl)-7-(triethylsilyloxy)nonane-3,4-diol 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: 71.0%

(((3R,4S,9S,(E))-9-(4-bromobenzyloxy)-4-(4-methoxybenzyloxy)-9-((R)-oxiran-2-yl)non-6-en-3-yl)oxy)triethylsilane (1384514-16-2) → (1S,3S,4S,6S,7R)-1-(4-bromobenzyloxy)-6-(4-methoxybenzyloxy)-1-((R)-oxiran-2-yl)-7-(triethylsilyloxy)nonane-3,4-diol (1384514-17-3) + (1S,3R,4R,6S,7R)-1-(4-bromobenzyloxy)-6-(4-methoxybenzyloxy)-1-((R)-oxiran-2-yl)-7-(triethylsilyloxy)nonane-3,4-diol (1384514-51-5)

Guidance literature:

With potassium osmate(VI) dihydrate; methanesulfonamide; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III); In water; tert-butyl alcohol; at 0 ℃; for 96h; optical yield given as %de;

DOI:10.1021/ja304554e

Reference yield:

(2R,3S)-1,2-epoxy-3-hydroxy-5-hexene (936724-50-4) → (1S,3R,4R,6S,7R)-1-(4-bromobenzyloxy)-6-(4-methoxybenzyloxy)-1-((R)-oxiran-2-yl)-7-(triethylsilyloxy)nonane-3,4-diol (1384514-51-5)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/ja304554e

Reference yield:

(3R,4S)-4-(4-methoxybenzyloxy)hept-6-en-3-ol (1384514-49-1) → (1S,3R,4R,6S,7R)-1-(4-bromobenzyloxy)-6-(4-methoxybenzyloxy)-1-((R)-oxiran-2-yl)-7-(triethylsilyloxy)nonane-3,4-diol (1384514-51-5)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; dmap; potassium osmate(VI) dihydrate; Hoveyda-Grubbs catalyst second generation; methanesulfonamide; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; p-benzoquinone; potassium hexacyanoferrate(III); In dichloromethane; water; 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

(R)-2-((S)-1-(4-bromobenzyloxy)but-3-enyl)oxirane

(((3R,4S,9S,(E))-9-(4-bromobenzyloxy)-4-(4-methoxybenzyloxy)-9-((R)-oxiran-2-yl)non-6-en-3-yl)oxy)triethylsilane

Downstream raw materials:

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

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

(S)-(1R,3S,4R)-1-((2R,4S,5S)-4-(4-bromobenzyloxy)-5-((methylsulfonyloxy)methyl)tetrahydrofuran-2-yl)-3-(4-methoxybenzyloxy)-4-(triethylsilyloxy)hexyl 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate

(R)-(1R,3S,4R)-1-((2R,4S,5S)-4-(4-bromobenzyloxy)-5-((methylsulfonyloxy)methyl)tetrahydrofuran-2-yl)-3-(4-methoxybenzyloxy)-4-(triethylsilyloxy)hexyl 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate

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