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

Base Information

Chemical Name: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
CAS No.:142866-03-3
Molecular Formula:C₄₂H₅₄O₁₄S₃Si
Molecular Weight:907.166
Hs Code.:

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

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Chemical Property of 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

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Technology Process of 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

There total 3 articles about 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 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%

: 142866-02-2
Acetic acid (2R,3S,4R)-4-hydroxy-2-(toluene-4-sulfonyloxymethyl)-3,4-dihydro-2H-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

: 142866-03-3,142926-93-0
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

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

: 142866-03-3,142926-93-0
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

Guidance literature:: Multi-step reaction with 2 steps

1: 75 percent / 3NH>F / acetonitrile / 23 °C

2: 91 percent / TMSOTf, molecular sieves 4 Angstroem / CH₂Cl₂ / 0.08 h / -78 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; triethylamine hydrofluoride; In dichloromethane; acetonitrile;
DOI:10.1021/jo00044a010

Reference yield:

: 136174-76-0,136174-77-1,136174-94-2,136174-95-3
4-O-acetyl-3-O-((tert-butyldimethyl)silyl)-2-deoxy-2-thiophenyl-6-O-tosyl-D-gluco-pyranose

: 142866-03-3,142926-93-0
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

Guidance literature:: Multi-step reaction with 2 steps

1: 58 percent / DBU / -20 °C

2: 91 percent / TMSOTf, molecular sieves 4 Angstroem / CH₂Cl₂ / 0.08 h / -78 °C

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;
DOI:10.1021/jo00044a010