2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1 → 4)-2,3-di-O-benzoyl-β-D-xylopyranoside trichloroacetimidate

Base Information

• Chemical Name: 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1 → 4)-2,3-di-O-benzoyl-β-D-xylopyranoside trichloroacetimidate
• CAS No.: 1352410-43-5
• Molecular Formula: C₅₅H₄₄Cl₃NO₁₆
• Molecular Weight: 1081.31
• Mol file: 1352410-43-5.mol

Synonyms:2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1 → 4)-2,3-di-O-benzoyl-β-D-xylopyranoside trichloroacetimidate

Chemical Property of 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1 → 4)-2,3-di-O-benzoyl-β-D-xylopyranoside trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1 → 4)-2,3-di-O-benzoyl-β-D-xylopyranoside trichloroacetimidate

There total 11 articles about 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1 → 4)-2,3-di-O-benzoyl-β-D-xylopyranoside 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: 83.0%

C53H44O16 + trichloroacetonitrile (545-06-2) → 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1 → 4)-2,3-di-O-benzoyl-β-D-xylopyranoside trichloroacetimidate (1352410-43-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.ejmech.2013.04.016

Reference yield:

4-methylphenyl 1-thio-β-D-xylopyranoside (67803-94-5) → 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1 → 4)-2,3-di-O-benzoyl-β-D-xylopyranoside trichloroacetimidate (1352410-43-5)

Guidance literature:

Multi-step reaction with 9 steps

1: trifluoroacetic acid / N,N-dimethyl-formamide / 12 h / 40 °C

2: toluene-4-sulfonic acid / methanol / 0 °C

3: pyridine; dmap / dichloromethane / 2 h

4: toluene-4-sulfonic acid / methanol; dichloromethane / 2 h

5: pyridine; dmap / dichloromethane / 3 h / 0 °C

6: acetyl chloride / methanol / 5 h / 0 °C

7: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / -78 - 20 °C / Molecular sieve

8: N-Bromosuccinimide / acetone; water / 0.08 h / -20 °C

9: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 20 °C

With pyridine; dmap; N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; acetyl chloride; trifluoroacetic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.ejmech.2013.04.016

Reference yield:

benzoyl chloride (98-88-4) → 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1 → 4)-2,3-di-O-benzoyl-β-D-xylopyranoside trichloroacetimidate (1352410-43-5)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine; dmap / dichloromethane / 3 h / 0 °C

2: acetyl chloride / methanol / 5 h / 0 °C

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / -78 - 20 °C / Molecular sieve

4: N-Bromosuccinimide / acetone; water / 0.08 h / -20 °C

5: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 20 °C

With pyridine; dmap; N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; acetyl chloride; In methanol; dichloromethane; water; acetone;

DOI:10.1016/j.ejmech.2013.04.016

upstream raw materials:

2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate

trichloroacetonitrile

4-methylphenyl 1-thio-β-D-xylopyranoside

1-(4-tolyl)thio-2,3-O-isopropylidene-4-O-(1-methoxy-1-methylethyl)-β-D-xylopyranoside

Downstream raw materials:

benzyl oleanolate 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1 → 4)-2,3-di-O-benzoyl-β-D-xylopyranosyl-(1 → 3)-2,4-di-O-acetyl-α-L-rhamnopyranosyl-(1 → 2)-3,4-O-isopropylidene-α-L-arabinopyranoside