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

Base Information

• Chemical Name: 4-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-thiophenyl-6-O-p-toluenesulfonyl-1-trichloroacetimido-α-D-glucopyranose
• CAS No.: 142865-94-9
• Molecular Formula: C₂₉H₃₈Cl₃NO₈S₂Si
• Molecular Weight: 727.199

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

Chemical Property of 4-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-thiophenyl-6-O-p-toluenesulfonyl-1-trichloroacetimido-α-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 4-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-thiophenyl-6-O-p-toluenesulfonyl-1-trichloroacetimido-α-D-glucopyranose

There total 9 articles about 4-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-thiophenyl-6-O-p-toluenesulfonyl-1-trichloroacetimido-α-D-glucopyranose 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: 91.0%

4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-thiophenyl-6-O-tosyl-D-gluco-pyranose (136174-76-0,136174-77-1,136174-94-2,136174-95-3) + trichloroacetonitrile (545-06-2) → 4-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-thiophenyl-6-O-p-toluenesulfonyl-1-trichloroacetimido-α-D-glucopyranose (142865-94-9)

Guidance literature:

With sodium hydride; at -20 ℃; for 1h;

DOI:10.1016/S0040-4020(97)90395-1

Reference yield: 81.0%

4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-thiophenyl-6-O-tosyl-α-D-gluco-pyranose (136174-76-0) + trichloroacetonitrile (545-06-2) → 4-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-thiophenyl-6-O-p-toluenesulfonyl-1-trichloroacetimido-α-D-glucopyranose (142865-94-9)

Guidance literature:

With sodium hydride; at -40 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/chem.201204545

Reference yield: 58.0%

4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-thiophenyl-6-O-tosyl-D-gluco-pyranose (136174-76-0,136174-77-1,136174-94-2,136174-95-3) + trichloroacetonitrile (545-06-2) → Acetic acid (2R,3R,4S,5S)-4-(tert-butyl-dimethyl-silanyloxy)-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester (142865-94-9,142866-06-6) + Acetic acid (2R,3R,4S,5R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester (142866-06-6) + 4-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-thiophenyl-6-O-p-toluenesulfonyl-1-trichloroacetimido-α-D-glucopyranose (142865-94-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; at -20 ℃; Yields of byproduct given;

DOI:10.1021/jo00044a010

upstream raw materials:

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

trichloroacetonitrile

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

benzenesulfenyl chloride

Downstream raw materials:

4-O-acetyl-3-O-(4-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-thiophenyl-6-O-p-toluenesulfonyl-α,β-D-glucopyranosyl)-2-deoxy-6-O-p-toluenesulfonyl-D-arabino-hex-1-enitol

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

Acetic acid (2R,3R,4S,5R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-((2R,3R,4S,5S,6R)-2,5-diacetoxy-6-methyl-3-phenylselanyl-tetrahydro-pyran-4-yloxy)-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

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