[(2R,3S,6R)-3-(tert-butyldimethylsilyloxy)-6-vinyltetrahydro-2H-pyran-2-yl]methyl 4-methylbenzenesulfonate

Base Information

Chemical Name:[(2R,3S,6R)-3-(tert-butyldimethylsilyloxy)-6-vinyltetrahydro-2H-pyran-2-yl]methyl 4-methylbenzenesulfonate
CAS No.:1354648-52-4
Molecular Formula:C₂₁H₃₄O₅SSi
Molecular Weight:426.649
Hs Code.:

Synonyms:[(2R,3S,6R)-3-(tert-butyldimethylsilyloxy)-6-vinyltetrahydro-2H-pyran-2-yl]methyl 4-methylbenzenesulfonate

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Chemical Property of [(2R,3S,6R)-3-(tert-butyldimethylsilyloxy)-6-vinyltetrahydro-2H-pyran-2-yl]methyl 4-methylbenzenesulfonate

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Technology Process of [(2R,3S,6R)-3-(tert-butyldimethylsilyloxy)-6-vinyltetrahydro-2H-pyran-2-yl]methyl 4-methylbenzenesulfonate

There total 12 articles about [(2R,3S,6R)-3-(tert-butyldimethylsilyloxy)-6-vinyltetrahydro-2H-pyran-2-yl]methyl 4-methylbenzenesulfonate 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: 95.0%

: 1354648-50-2
[(2R,3S,6R)-3-(tert-butyldimethylsilyloxy)-6-vinyltetrahydro-2H-pyran-2-yl]methanol

: 98-59-9
p-toluenesulfonyl chloride

: 1354648-52-4
[(2R,3S,6R)-3-(tert-butyldimethylsilyloxy)-6-vinyltetrahydro-2H-pyran-2-yl]methyl 4-methylbenzenesulfonate

Guidance literature:: With pyridine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1055/s-0030-1260203

Reference yield:

: 1188304-30-4
(4aR,8R,8aS)-2,2-di-tert-butyl-8-(vinyloxy)-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3,2]dioxasiline

: 1354648-52-4
[(2R,3S,6R)-3-(tert-butyldimethylsilyloxy)-6-vinyltetrahydro-2H-pyran-2-yl]methyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 9 steps

1: toluene / 5 h / 185 °C / Sealed tube

2: palladium 10% on activated carbon; hydrogen / methanol

3: sodium tetrahydroborate / methanol / 3 h / 0 - 20 °C

4: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran / 0 - 20 °C

5: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C

6: tetrabutyl ammonium fluoride / tetrahydrofuran / 48 h / 20 °C

7: 1H-imidazole; dmap / tetrahydrofuran / 15 h / 20 °C

8: pyridinium p-toluenesulfonate / methanol / 22 h / 0 - 20 °C

9: pyridine / dichloromethane / 0 - 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; palladium 10% on activated carbon; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; pyridinium p-toluenesulfonate; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: Claisen rearrangement;
DOI:10.1055/s-0030-1260203

Reference yield:

: 1188304-26-8
2-{(4aR,6S,8aS)-2,2-di-tert-butyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl}acetaldehyde

: 1354648-52-4
[(2R,3S,6R)-3-(tert-butyldimethylsilyloxy)-6-vinyltetrahydro-2H-pyran-2-yl]methyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 8 steps

1: palladium 10% on activated carbon; hydrogen / methanol

2: sodium tetrahydroborate / methanol / 3 h / 0 - 20 °C

3: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran / 0 - 20 °C

4: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 48 h / 20 °C

6: 1H-imidazole; dmap / tetrahydrofuran / 15 h / 20 °C

7: pyridinium p-toluenesulfonate / methanol / 22 h / 0 - 20 °C

8: pyridine / dichloromethane / 0 - 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; palladium 10% on activated carbon; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; iodine; pyridinium p-toluenesulfonate; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1055/s-0030-1260203