methyl 6-bromo-4-O-benzoyl-3-trifluoroacetamido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside

Base Information

• Chemical Name: methyl 6-bromo-4-O-benzoyl-3-trifluoroacetamido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside
• CAS No.: 188349-19-1
• Molecular Formula: C₁₆H₁₇BrF₃NO₅
• Molecular Weight: 440.214
• Mol file: 188349-19-1.mol

Synonyms:methyl 6-bromo-4-O-benzoyl-3-trifluoroacetamido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside

Chemical Property of methyl 6-bromo-4-O-benzoyl-3-trifluoroacetamido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-bromo-4-O-benzoyl-3-trifluoroacetamido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside

There total 14 articles about methyl 6-bromo-4-O-benzoyl-3-trifluoroacetamido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside 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: 72.0%

methyl 3-trifluoroacetamido-4,6-O-benzylidene-2,3-dideoxy-α-L-lyxo-hexopyranoside (143728-45-4) → methyl 6-bromo-4-O-benzoyl-3-trifluoroacetamido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside (188349-19-1)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); barium carbonate; In tetrachloromethane; at 20 - 80 ℃; for 1.5h;

DOI:10.1080/07328309708006508

Reference yield:

3-azido-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose (35085-25-7) → methyl 6-bromo-4-O-benzoyl-3-trifluoroacetamido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside (188349-19-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: pyridine / 6.5 h / 0 - 20 °C

2.1: 13.41 g / pyridine / 16.5 h / 0 - 20 °C

3.1: 78 percent / dimethylformamide / 72 h / 120 °C

4.1: p-toluenesulfonic acid / CH₂Cl₂; methanol / 1.5 h / 20 °C

5.1: 0.94 g / sodium methoxide / methanol / 1 h / 20 °C

6.1: hydrochloric acid; water / 9 h / 75 °C

6.2: 63 percent / ZnCl₂ / 9.5 h / 20 °C

7.1: 95 percent / hydrogen / Pd/C / ethanol; triethylamine / 4 h / 20 °C / 760 Torr

8.1: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

9.1: 85 percent / pyridine / 19.3 h / 0 - 20 °C

10.1: 80 percent / tributyltin hydride; AIBN / toluene / 1.5 h / 20 - 60 °C

11.1: 72 percent / N-bromosuccinimide; barium carbonate; AIBN / CCl₄ / 1.5 h / 20 - 80 °C

With pyridine; hydrogenchloride; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); water; hydrogen; tri-n-butyl-tin hydride; sodium methylate; toluene-4-sulfonic acid; triethylamine; barium carbonate; palladium on activated charcoal; In methanol; tetrachloromethane; ethanol; dichloromethane; triethylamine; N,N-dimethyl-formamide; toluene; 1.1: Etherification / 2.1: mesylation / 3.1: Substitution / 4.1: dealkylation / 5.1: deacylation / 6.1: Hydrolysis / 6.2: ketalization / 7.1: Hydrogenation / 8.1: Acylation / 9.1: Esterification / 10.1: deoxygenation / 11.1: Ring cleavage;

DOI:10.1080/07328309708006508

Reference yield:

1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose (55951-93-4) → methyl 6-bromo-4-O-benzoyl-3-trifluoroacetamido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside (188349-19-1)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 48 percent / sodium azide / dimethylformamide / 24 h / 50 °C

2.1: 98 percent / AcOH; H₂O / methanol / 17 h / 50 °C

3.1: pyridine / 6.5 h / 0 - 20 °C

4.1: 13.41 g / pyridine / 16.5 h / 0 - 20 °C

5.1: 78 percent / dimethylformamide / 72 h / 120 °C

6.1: p-toluenesulfonic acid / CH₂Cl₂; methanol / 1.5 h / 20 °C

7.1: 0.94 g / sodium methoxide / methanol / 1 h / 20 °C

8.1: hydrochloric acid; water / 9 h / 75 °C

8.2: 63 percent / ZnCl₂ / 9.5 h / 20 °C

9.1: 95 percent / hydrogen / Pd/C / ethanol; triethylamine / 4 h / 20 °C / 760 Torr

10.1: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

11.1: 85 percent / pyridine / 19.3 h / 0 - 20 °C

12.1: 80 percent / tributyltin hydride; AIBN / toluene / 1.5 h / 20 - 60 °C

13.1: 72 percent / N-bromosuccinimide; barium carbonate; AIBN / CCl₄ / 1.5 h / 20 - 80 °C

With pyridine; hydrogenchloride; N-Bromosuccinimide; sodium azide; 2,2'-azobis(isobutyronitrile); water; hydrogen; tri-n-butyl-tin hydride; sodium methylate; toluene-4-sulfonic acid; acetic acid; triethylamine; barium carbonate; palladium on activated charcoal; In methanol; tetrachloromethane; ethanol; dichloromethane; triethylamine; N,N-dimethyl-formamide; toluene; 1.1: Substitution / 2.1: Hydrolysis / 3.1: Etherification / 4.1: mesylation / 5.1: Substitution / 6.1: dealkylation / 7.1: deacylation / 8.1: Hydrolysis / 8.2: ketalization / 9.1: Hydrogenation / 10.1: Acylation / 11.1: Esterification / 12.1: deoxygenation / 13.1: Ring cleavage;

DOI:10.1080/07328309708006508

upstream raw materials:

methyl 3-trifluoroacetamido-4,6-O-benzylidene-2,3-dideoxy-α-L-lyxo-hexopyranoside

3-azido-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose

3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose

Downstream raw materials:

methyl 4-O-benzoyl-3-trifluoroacetamido-2,3,6-trideoxy-α-L-lyxo-hexopyranoside