2-Trimethylsilanyl-ethanesulfonic acid ((2R,4aR,6S,7S,8R,8aR)-8-benzyloxy-7-bromo-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-amide

Base Information

• Chemical Name: 2-Trimethylsilanyl-ethanesulfonic acid ((2R,4aR,6S,7S,8R,8aR)-8-benzyloxy-7-bromo-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-amide
• CAS No.: 183989-00-6
• Molecular Formula: C₂₅H₃₄BrNO₆SSi
• Molecular Weight: 584.604
• Mol file: 183989-00-6.mol

Synonyms:2-Trimethylsilanyl-ethanesulfonic acid ((2R,4aR,6S,7S,8R,8aR)-8-benzyloxy-7-bromo-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-amide

Chemical Property of 2-Trimethylsilanyl-ethanesulfonic acid ((2R,4aR,6S,7S,8R,8aR)-8-benzyloxy-7-bromo-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Trimethylsilanyl-ethanesulfonic acid ((2R,4aR,6S,7S,8R,8aR)-8-benzyloxy-7-bromo-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-amide

There total 7 articles about 2-Trimethylsilanyl-ethanesulfonic acid ((2R,4aR,6S,7S,8R,8aR)-8-benzyloxy-7-bromo-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-amide 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:

benzaldehyde dimethyl acetal (1125-88-8) → 2-Trimethylsilanyl-ethanesulfonic acid ((2R,4aR,6S,7S,8R,8aR)-8-benzyloxy-7-bromo-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-amide (183989-00-6)

Guidance literature:

Multi-step reaction with 4 steps

1: p-toluenesulfonic acid / dimethylformamide / 9 h / 20 - 30 °C

2: 86 percent / 3,3-dimethyldioxirane / acetone; CH₂Cl₂ / -78 °C

3: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, RT, 30 min, 2.) THF, RT, 14 h

4: 2.) NH₄I / 1.) CH₂Cl₂, 0 deg C, 2.) ethanol

With ammonium iodide; 3,3-dimethyldioxirane; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja960526c

Reference yield:

thiophenyl 2,3-dideoxy-α-D-glucopyranoside (111425-52-6) → 2-Trimethylsilanyl-ethanesulfonic acid ((2R,4aR,6S,7S,8R,8aR)-8-benzyloxy-7-bromo-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-amide (183989-00-6)

Guidance literature:

Multi-step reaction with 4 steps

1: p-toluenesulfonic acid / dimethylformamide / 9 h / 20 - 30 °C

2: 86 percent / 3,3-dimethyldioxirane / acetone; CH₂Cl₂ / -78 °C

3: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, RT, 30 min, 2.) THF, RT, 14 h

4: 2.) NH₄I / 1.) CH₂Cl₂, 0 deg C, 2.) ethanol

With ammonium iodide; 3,3-dimethyldioxirane; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja960526c

Reference yield:

phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside (111425-49-1,125848-19-3,137740-45-5,111425-48-0,286410-13-7) → 2-Trimethylsilanyl-ethanesulfonic acid ((2R,4aR,6S,7S,8R,8aR)-8-benzyloxy-7-bromo-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-amide (183989-00-6)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium methoxide / methanol / 1 h

2: p-toluenesulfonic acid / dimethylformamide / 9 h / 20 - 30 °C

3: 86 percent / 3,3-dimethyldioxirane / acetone; CH₂Cl₂ / -78 °C

4: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, RT, 30 min, 2.) THF, RT, 14 h

5: 2.) NH₄I / 1.) CH₂Cl₂, 0 deg C, 2.) ethanol

With ammonium iodide; sodium methylate; 3,3-dimethyldioxirane; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja960526c

upstream raw materials:

1,5-anhydro-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose

N,N-dibromo-2-(trimethylsilyl)ethanesulfonamide

1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose

benzaldehyde dimethyl acetal

Downstream raw materials:

2-Trimethylsilanyl-ethanesulfonic acid {(2R,4aR,6S,7R,8S,8aS)-8-benzyloxy-6-[(2R,3S,4S)-2-benzyloxymethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-3,4-dihydro-2H-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-amide

N-[(2R,4aR,6R,7R,8S,8aS)-6-((4aS,6R,7R,7aR)-5-Benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-yloxy)-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

2-Trimethylsilanyl-ethanesulfonic acid [(2R,4aR,6R,7R,8S,8aS)-6-((4aS,6R,7R,7aR)-5-benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-yloxy)-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-amide