3,4-dihydroxy-2-(4-methylphenylsulfonyloxymethyl)-5-vinyl-(2S,3S,4R)-tetrahydrofuran

Base Information

Chemical Name:3,4-dihydroxy-2-(4-methylphenylsulfonyloxymethyl)-5-vinyl-(2S,3S,4R)-tetrahydrofuran
CAS No.:1373612-90-8
Molecular Formula:C₁₄H₁₈O₆S
Molecular Weight:314.359
Hs Code.:

Synonyms:3,4-dihydroxy-2-(4-methylphenylsulfonyloxymethyl)-5-vinyl-(2S,3S,4R)-tetrahydrofuran

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Chemical Property of 3,4-dihydroxy-2-(4-methylphenylsulfonyloxymethyl)-5-vinyl-(2S,3S,4R)-tetrahydrofuran

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Technology Process of 3,4-dihydroxy-2-(4-methylphenylsulfonyloxymethyl)-5-vinyl-(2S,3S,4R)-tetrahydrofuran

There total 6 articles about 3,4-dihydroxy-2-(4-methylphenylsulfonyloxymethyl)-5-vinyl-(2S,3S,4R)-tetrahydrofuran 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: 84.0%

: 1373612-88-4
2,2-dimethyl-4-(4-methylphenylsulfonyloxymethyl)-6-vinyl-(3aR,4S,6aS)-perhydrofuro[3,4-d][1,3]dioxole

: 1373612-90-8
3,4-dihydroxy-2-(4-methylphenylsulfonyloxymethyl)-5-vinyl-(2S,3S,4R)-tetrahydrofuran

Guidance literature:: With sulfuric acid; water; In 1,4-dioxane; at 80 ℃; for 2h;
DOI:10.1016/j.carres.2012.01.018

Reference yield:

: 7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4
2,3,5,6-di-O-isopropylidene-D-mannofuranose

: 1373612-90-8
3,4-dihydroxy-2-(4-methylphenylsulfonyloxymethyl)-5-vinyl-(2S,3S,4R)-tetrahydrofuran

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium tert-butylate / dimethyl sulfoxide / 0.5 h / 10 °C

1.2: 10 - 20 °C

2.1: pyridine; dmap / 3.5 h / 0 - 20 °C

3.1: bismuth(III) chloride / dichloromethane / 2 h / 20 °C

4.1: 1H-imidazole; iodine; triphenylphosphine / toluene / Heating

5.1: sulfuric acid; water / 1,4-dioxane / 2 h / 80 °C

With pyridine; 1H-imidazole; dmap; bismuth(III) chloride; sulfuric acid; potassium tert-butylate; water; iodine; triphenylphosphine; In 1,4-dioxane; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1016/j.carres.2012.01.018

Reference yield:

: 1373612-84-0
6-(2,2-dimethyl-1,3-dioxolan-4yl)-2,2-dimethyl-4-(4-methylphenylsulfonyloxymethyl)-(3aR,4S,6aS)-perhydrofuro[3,4-d][1,3]dioxole

: 1373612-90-8
3,4-dihydroxy-2-(4-methylphenylsulfonyloxymethyl)-5-vinyl-(2S,3S,4R)-tetrahydrofuran

Guidance literature:: Multi-step reaction with 3 steps

1: bismuth(III) chloride / dichloromethane / 2 h / 20 °C

2: 1H-imidazole; iodine; triphenylphosphine / toluene / Heating

3: sulfuric acid; water / 1,4-dioxane / 2 h / 80 °C

With 1H-imidazole; bismuth(III) chloride; sulfuric acid; water; iodine; triphenylphosphine; In 1,4-dioxane; dichloromethane; toluene;
DOI:10.1016/j.carres.2012.01.018