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

Base Information

• Chemical Name: 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
• CAS No.: 183989-04-0
• Molecular Formula: C₄₄H₆₃NO₁₁SSi₂
• Molecular Weight: 870.221
• Mol file: 183989-04-0.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 12 articles about 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 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: 63.0%

1,5-anhydro-6-O-benzyl-2-deoxy-3-O-<<2-(trimethylsilyl)ethoxy>methyl>-D-ribo-hex-1-enopyranose (134756-60-8) + 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) → 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 (183989-04-0)

Guidance literature:

With potassium hexamethylsilazane; In N,N-dimethyl-formamide; at -40 - 20 ℃;

DOI:10.1021/ja960526c

Reference yield:

1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose (63598-38-9,167074-37-5) → 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 (183989-04-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 5 h / Ambient temperature

2: 99 percent / sodium, ammonia (liquid) / tetrahydrofuran / 0.02 h / -78 °C

3: 1.) dibutyltin oxide, 2.) CsF / 1.) methanol, reflux, 1 h, 2.) DMF, 24 h

4: 63 percent / KHMDS / dimethylformamide / -40 - 20 °C

With ammonia; sodium; potassium hexamethylsilazane; di(n-butyl)tin oxide; N-ethyl-N,N-diisopropylamine; cesium fluoride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja960526c

Reference yield:

2-(trimethylsilyl)ethanesulfonamide (125486-96-6) → 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 (183989-04-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 35 percent / bromine, aq. NaOH

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

3: 63 percent / KHMDS / dimethylformamide / -40 - 20 °C

With ammonium iodide; sodium hydroxide; bromine; potassium hexamethylsilazane; In N,N-dimethyl-formamide;

DOI:10.1021/ja960526c

upstream raw materials:

1,5-anhydro-6-O-benzyl-2-deoxy-3-O-<<2-(trimethylsilyl)ethoxy>methyl>-D-ribo-hex-1-enopyranose

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

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

2-(trimethylsilyl)ethanesulfonamide