2-(trimethylsilyl)ethyl 4-O-acetyl-3-O-(4-O-acetyl-2-deoxy-3-O-(tert-butyldimethylsilyl)-2-thiophenyl-6-O-p-toluenesulfonyl-α,β-D-glucopyranosyl)-2-deoxy-6-O-p-toluenesulfonyl-α-D-arabino-hexopyranose

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 4-O-acetyl-3-O-(4-O-acetyl-2-deoxy-3-O-(tert-butyldimethylsilyl)-2-thiophenyl-6-O-p-toluenesulfonyl-α,β-D-glucopyranosyl)-2-deoxy-6-O-p-toluenesulfonyl-α-D-arabino-hexopyranose
CAS No.:142865-98-3
Molecular Formula:C₄₇H₆₈O₁₅S₃Si₂
Molecular Weight:1025.42
Hs Code.:

2-(trimethylsilyl)ethyl 4-O-acetyl-3-O-(4-O-acetyl-2-deoxy-3-O-(tert-butyldimethylsilyl)-2-thiophenyl-6-O-p-toluenesulfonyl-α,β-D-glucopyranosyl)-2-deoxy-6-O-p-toluenesulfonyl-α-D-arabino-hexopyranose

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Chemical Property of 2-(trimethylsilyl)ethyl 4-O-acetyl-3-O-(4-O-acetyl-2-deoxy-3-O-(tert-butyldimethylsilyl)-2-thiophenyl-6-O-p-toluenesulfonyl-α,β-D-glucopyranosyl)-2-deoxy-6-O-p-toluenesulfonyl-α-D-arabino-hexopyranose

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Technology Process of 2-(trimethylsilyl)ethyl 4-O-acetyl-3-O-(4-O-acetyl-2-deoxy-3-O-(tert-butyldimethylsilyl)-2-thiophenyl-6-O-p-toluenesulfonyl-α,β-D-glucopyranosyl)-2-deoxy-6-O-p-toluenesulfonyl-α-D-arabino-hexopyranose

There total 6 articles about 2-(trimethylsilyl)ethyl 4-O-acetyl-3-O-(4-O-acetyl-2-deoxy-3-O-(tert-butyldimethylsilyl)-2-thiophenyl-6-O-p-toluenesulfonyl-α,β-D-glucopyranosyl)-2-deoxy-6-O-p-toluenesulfonyl-α-D-arabino-hexopyranose 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%

: 142865-97-2
Acetic acid (2R,3S,4R,6S)-4-hydroxy-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

: 142865-94-9
4-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-thiophenyl-6-O-p-toluenesulfonyl-1-trichloroacetimido-α-D-glucopyranose

: 142865-98-3,142866-09-9,142866-10-2
2-(trimethylsilyl)ethyl 4-O-acetyl-3-O-(4-O-acetyl-2-deoxy-3-O-(tert-butyldimethylsilyl)-2-thiophenyl-6-O-p-toluenesulfonyl-α,β-D-glucopyranosyl)-2-deoxy-6-O-p-toluenesulfonyl-α-D-arabino-hexopyranose

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -78 ℃; for 0.0833333h;
DOI:10.1021/jo00044a010

Reference yield:

: 129693-97-6
4-O-Acetyl-3-O-tert-butyldimethylsilyl-6-O-tosyl-D-glucal

: 142865-98-3,142866-09-9,142866-10-2
2-(trimethylsilyl)ethyl 4-O-acetyl-3-O-(4-O-acetyl-2-deoxy-3-O-(tert-butyldimethylsilyl)-2-thiophenyl-6-O-p-toluenesulfonyl-α,β-D-glucopyranosyl)-2-deoxy-6-O-p-toluenesulfonyl-α-D-arabino-hexopyranose

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / NIS / acetonitrile

2: 62 percent / 3NH>F / acetonitrile / 23 °C

3: 92 percent / Ph₃SnH, AIBN / toluene / 80 °C

4: 95 percent / TMSOTf, molecular sieves 4 Angstroem / CH₂Cl₂ / 0.08 h / -78 °C

With N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; triphenylstannane; triethylamine hydrofluoride; In dichloromethane; toluene; acetonitrile;
DOI:10.1021/jo00044a010

Reference yield:

: 142865-95-0,142866-07-7
Acetic acid (2R,3R,4S,5R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-5-iodo-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester

: 142865-98-3,142866-09-9,142866-10-2
2-(trimethylsilyl)ethyl 4-O-acetyl-3-O-(4-O-acetyl-2-deoxy-3-O-(tert-butyldimethylsilyl)-2-thiophenyl-6-O-p-toluenesulfonyl-α,β-D-glucopyranosyl)-2-deoxy-6-O-p-toluenesulfonyl-α-D-arabino-hexopyranose

Guidance literature:: Multi-step reaction with 3 steps

1: 62 percent / 3NH>F / acetonitrile / 23 °C

2: 92 percent / Ph₃SnH, AIBN / toluene / 80 °C

3: 95 percent / TMSOTf, molecular sieves 4 Angstroem / CH₂Cl₂ / 0.08 h / -78 °C

With 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; triphenylstannane; triethylamine hydrofluoride; In dichloromethane; toluene; acetonitrile;
DOI:10.1021/jo00044a010