2,3-di-O-benzoyl-4-O-(2',3',4',6'-tetra-O-benzoyl-β-D-glycopyranosyl)-1-thio-α-L-rhamnopyranoside trichloroacetimidate

Base Information

Chemical Name:2,3-di-O-benzoyl-4-O-(2',3',4',6'-tetra-O-benzoyl-β-D-glycopyranosyl)-1-thio-α-L-rhamnopyranoside trichloroacetimidate
CAS No.:1309374-68-2
Molecular Formula:C₅₆H₄₆Cl₃NO₁₆
Molecular Weight:1095.34
Hs Code.:

Synonyms:2,3-di-O-benzoyl-4-O-(2',3',4',6'-tetra-O-benzoyl-β-D-glycopyranosyl)-1-thio-α-L-rhamnopyranoside trichloroacetimidate

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Chemical Property of 2,3-di-O-benzoyl-4-O-(2',3',4',6'-tetra-O-benzoyl-β-D-glycopyranosyl)-1-thio-α-L-rhamnopyranoside trichloroacetimidate

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Technology Process of 2,3-di-O-benzoyl-4-O-(2',3',4',6'-tetra-O-benzoyl-β-D-glycopyranosyl)-1-thio-α-L-rhamnopyranoside trichloroacetimidate

There total 6 articles about 2,3-di-O-benzoyl-4-O-(2',3',4',6'-tetra-O-benzoyl-β-D-glycopyranosyl)-1-thio-α-L-rhamnopyranoside trichloroacetimidate 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:

: 1309374-72-8
2,3-di-O-benzoyl-4-O-(2',3',4',6'-tetra-O-benzoyl-β-D-glycopyranosyl)-α-L-rhamnopyranose

: 545-06-2
trichloroacetonitrile

: 1309374-68-2
2,3-di-O-benzoyl-4-O-(2',3',4',6'-tetra-O-benzoyl-β-D-glycopyranosyl)-1-thio-α-L-rhamnopyranoside trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 1.5h;
DOI:10.1016/j.steroids.2011.02.010

Reference yield:

: 131087-35-9
phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

: 1309374-68-2
2,3-di-O-benzoyl-4-O-(2',3',4',6'-tetra-O-benzoyl-β-D-glycopyranosyl)-1-thio-α-L-rhamnopyranoside trichloroacetimidate

Guidance literature:: Multi-step reaction with 5 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.17 h / -20 °C / Molecular sieve

1.2: -20 °C

2.1: acetic acid / 5 h / 80 °C

3.1: pyridine / 4 h

4.1: N-Bromosuccinimide; water / acetone / 0 - 20 °C

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / 0 °C

With pyridine; N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; water; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetone;
DOI:10.1016/j.steroids.2011.02.010

Reference yield:

: 149707-76-6
O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl) trichloroacetimidate

: 1309374-68-2
2,3-di-O-benzoyl-4-O-(2',3',4',6'-tetra-O-benzoyl-β-D-glycopyranosyl)-1-thio-α-L-rhamnopyranoside trichloroacetimidate

Guidance literature:: Multi-step reaction with 5 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.17 h / -20 °C / Molecular sieve

1.2: -20 °C

2.1: acetic acid / 5 h / 80 °C

3.1: pyridine / 4 h

4.1: N-Bromosuccinimide; water / acetone / 0 - 20 °C

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1.5 h / 0 °C

With pyridine; N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; water; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetone;
DOI:10.1016/j.steroids.2011.02.010