4-(trifluoroacetamido)phenyl-2-acetamido-2-deoxy-4-O-beta-mannopyranosyl-beta-glucopyranoside

Base Information

• Chemical Name: 4-(trifluoroacetamido)phenyl-2-acetamido-2-deoxy-4-O-beta-mannopyranosyl-beta-glucopyranoside
• CAS No.: 92689-45-7
• Molecular Formula: C22H29 F3 N2 O12
• Molecular Weight: 570.4670696
• Mol file: 92689-45-7.mol

Synonyms:4-(trifluoroacetamido)phenyl-2-acetamido-2-deoxy-4-O-beta-mannopyranosyl-beta-glucopyranoside

Chemical Property of 4-(trifluoroacetamido)phenyl-2-acetamido-2-deoxy-4-O-beta-mannopyranosyl-beta-glucopyranoside

Chemical Property:

• Vapor Pressure: 3.58E-33mmHg at 25°C
• Boiling Point: 880.2°Cat760mmHg
• Flash Point: 486.1°C
• Density: 1.62g/cm³

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(trifluoroacetamido)phenyl-2-acetamido-2-deoxy-4-O-beta-mannopyranosyl-beta-glucopyranoside

There total 12 articles about 4-(trifluoroacetamido)phenyl-2-acetamido-2-deoxy-4-O-beta-mannopyranosyl-beta-glucopyranoside 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: 70.0%

p-(trifluoroacetamido)phenyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-β-D-glucopyranoside (92689-44-6) → p-(trifluoroacetamido)phenyl 2-acetamido-2-deoxy-4-O-β-D-mannopyranosyl-β-D-glucopyranoside (92689-45-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; for 16h;

DOI:10.1016/0008-6215(84)85320-3

Reference yield:

2,3,4,6-tetra-O-benzoylglucosyl bromide (14218-11-2) → p-(trifluoroacetamido)phenyl 2-acetamido-2-deoxy-4-O-β-D-mannopyranosyl-β-D-glucopyranoside (92689-45-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 2,4,6-collidine / nitromethane / 72 h / 37 °C

2: 12.9 g / sodium methoxide / methanol / Ambient temperature

3: 1.)sodium hydride / 1.) DMF

4: trimethylsilyl bromide / toluene / 1.5 h / Ambient temperature

5: 57 percent / silver triflate, 2,4,6-collidine / toluene; nitromethane / -25 °C

6: 92 percent / barium oxide / methanol; CH₂Cl₂ / 2 h / Heating

7: dimethyl sulfoxide, acetic anhydride / 48 h / Ambient temperature

8: 75 percent / lithium tris(1-methylpropyl)borohydride / tetrahydrofuran / 3 h / -75 °C

9: H₂ / Adam's catalyst / ethyl acetate / Ambient temperature

10: 98 percent / pyridine / ethyl acetate / 0.33 h / 60 °C

11: 70 percent / H₂ / Pd/C / acetic acid / 16 h

With pyridine; 2,4,6-trimethyl-pyridine; trimethylsilyl bromide; hydrogen; sodium methylate; silver trifluoromethanesulfonate; acetic anhydride; L-Selectride; sodium hydride; dimethyl sulfoxide; barium(II) oxide; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; nitromethane; dichloromethane; acetic acid; ethyl acetate; toluene;

DOI:10.1016/0008-6215(84)85320-3

Reference yield:

2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide (40246-28-4) → p-(trifluoroacetamido)phenyl 2-acetamido-2-deoxy-4-O-β-D-mannopyranosyl-β-D-glucopyranoside (92689-45-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 57 percent / silver triflate, 2,4,6-collidine / toluene; nitromethane / -25 °C

2: 92 percent / barium oxide / methanol; CH₂Cl₂ / 2 h / Heating

3: dimethyl sulfoxide, acetic anhydride / 48 h / Ambient temperature

4: 75 percent / lithium tris(1-methylpropyl)borohydride / tetrahydrofuran / 3 h / -75 °C

5: H₂ / Adam's catalyst / ethyl acetate / Ambient temperature

6: 98 percent / pyridine / ethyl acetate / 0.33 h / 60 °C

7: 70 percent / H₂ / Pd/C / acetic acid / 16 h

With pyridine; 2,4,6-trimethyl-pyridine; hydrogen; silver trifluoromethanesulfonate; acetic anhydride; L-Selectride; dimethyl sulfoxide; barium(II) oxide; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; nitromethane; dichloromethane; acetic acid; ethyl acetate; toluene;

DOI:10.1016/0008-6215(84)85320-3

upstream raw materials:

p-(trifluoroacetamido)phenyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-β-D-glucopyranoside

2,3,4,6-tetra-O-benzoylglucosyl bromide

2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-glucopyranosyl bromide

p-nitrophenyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Refernces