Acetic acid (2R,3S,4S,5R,6S)-6-[(2R,3S,4R,6S)-3-acetoxy-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-4-hydroxy-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,5R,6S)-6-[(2R,3S,4R,6S)-3-acetoxy-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-4-hydroxy-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester
• CAS No.: 142866-11-3
• Molecular Formula: C₄₁H₅₄O₁₅S₃Si
• Molecular Weight: 911.154

Synonyms:Acetic acid (2R,3S,4S,5R,6S)-6-[(2R,3S,4R,6S)-3-acetoxy-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-4-hydroxy-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3S,4S,5R,6S)-6-[(2R,3S,4R,6S)-3-acetoxy-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-4-hydroxy-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Acetic acid (2R,3S,4S,5R,6S)-6-[(2R,3S,4R,6S)-3-acetoxy-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-4-hydroxy-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

There total 8 articles about Acetic acid (2R,3S,4S,5R,6S)-6-[(2R,3S,4R,6S)-3-acetoxy-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-4-hydroxy-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester 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: 56.0%

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 (142865-98-3,142866-09-9,142866-10-2) → Acetic acid (2R,3S,4S,5R,6S)-6-[(2R,3S,4R,6S)-3-acetoxy-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-4-hydroxy-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester (142866-11-3) + Acetic acid (2R,3S,4S,5R,6R)-6-[(2R,3S,4R,6S)-3-acetoxy-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-4-hydroxy-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester (142865-99-4)

Guidance literature:

With triethylamine hydrofluoride; In acetonitrile; at 23 ℃;

DOI:10.1021/jo00044a010

Reference yield:

4-O-Acetyl-3-O-tert-butyldimethylsilyl-6-O-tosyl-D-glucal (129693-97-6) → Acetic acid (2R,3S,4S,5R,6S)-6-[(2R,3S,4R,6S)-3-acetoxy-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-4-hydroxy-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester (142866-11-3)

Guidance literature:

Multi-step reaction with 5 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

5: 3NH>F / acetonitrile / 23 °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:

Acetic acid (2R,3S,4R,6S)-4-hydroxy-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3-yl ester (142865-97-2) → Acetic acid (2R,3S,4S,5R,6S)-6-[(2R,3S,4R,6S)-3-acetoxy-2-(toluene-4-sulfonyloxymethyl)-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-4-yloxy]-4-hydroxy-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester (142866-11-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / TMSOTf, molecular sieves 4 Angstroem / CH₂Cl₂ / 0.08 h / -78 °C

2: 3NH>F / acetonitrile / 23 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; triethylamine hydrofluoride; In dichloromethane; acetonitrile;

DOI:10.1021/jo00044a010

upstream raw materials:

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

4-O-Acetyl-3-O-tert-butyldimethylsilyl-6-O-tosyl-D-glucal

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

4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-thiophenyl-6-O-tosyl-D-gluco-pyranose

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