[(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
• Mol file: 1354648-52-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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%

[(2R,3S,6R)-3-(tert-butyldimethylsilyloxy)-6-vinyltetrahydro-2H-pyran-2-yl]methanol (1354648-50-2) + p-toluenesulfonyl chloride (98-59-9) → [(2R,3S,6R)-3-(tert-butyldimethylsilyloxy)-6-vinyltetrahydro-2H-pyran-2-yl]methyl 4-methylbenzenesulfonate (1354648-52-4)

Guidance literature:

With pyridine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1055/s-0030-1260203

Reference yield:

(4aR,8R,8aS)-2,2-di-tert-butyl-8-(vinyloxy)-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3,2]dioxasiline (1188304-30-4) → [(2R,3S,6R)-3-(tert-butyldimethylsilyloxy)-6-vinyltetrahydro-2H-pyran-2-yl]methyl 4-methylbenzenesulfonate (1354648-52-4)

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:

2-{(4aR,6S,8aS)-2,2-di-tert-butyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3,2]dioxasilin-6-yl}acetaldehyde (1188304-26-8) → [(2R,3S,6R)-3-(tert-butyldimethylsilyloxy)-6-vinyltetrahydro-2H-pyran-2-yl]methyl 4-methylbenzenesulfonate (1354648-52-4)

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

upstream raw materials:

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

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

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

p-toluenesulfonyl chloride