2-(4-trifluoroacetamidophenyl)ethyl 2,6,7-tri-O-acetyl-4-O-chloroacetyl-L-glycero-α-D-manno-heptopyranoside

Base Information

• Chemical Name: 2-(4-trifluoroacetamidophenyl)ethyl 2,6,7-tri-O-acetyl-4-O-chloroacetyl-L-glycero-α-D-manno-heptopyranoside
• CAS No.: 142270-26-6
• Molecular Formula: C₂₅H₂₉ClF₃NO₁₂
• Molecular Weight: 627.953
• Mol file: 142270-26-6.mol

Synonyms:2-(4-trifluoroacetamidophenyl)ethyl 2,6,7-tri-O-acetyl-4-O-chloroacetyl-L-glycero-α-D-manno-heptopyranoside

Chemical Property of 2-(4-trifluoroacetamidophenyl)ethyl 2,6,7-tri-O-acetyl-4-O-chloroacetyl-L-glycero-α-D-manno-heptopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(4-trifluoroacetamidophenyl)ethyl 2,6,7-tri-O-acetyl-4-O-chloroacetyl-L-glycero-α-D-manno-heptopyranoside

There total 9 articles about 2-(4-trifluoroacetamidophenyl)ethyl 2,6,7-tri-O-acetyl-4-O-chloroacetyl-L-glycero-α-D-manno-heptopyranoside 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:

methyl-2,3,4-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside (122588-51-6) → 2-(4-trifluoroacetamidophenyl)ethyl 2,6,7-tri-O-acetyl-4-O-chloroacetyl-L-glycero-α-D-manno-heptopyranoside (142270-26-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / 4-dimethylaminopyridine / pyridine / 2 h / Ambient temperature

2: conc. H₂SO₄ / acetic acid / 0.17 h

3: 78 percent / ZnCl₂ / CH₂Cl₂ / 3 h

4: 1) silver triflate, N-iodosuccinimide, 2) BF₃-etherate / 1) CH₂Cl₂, CH₃CN, 10 min, 2) CH₃CN, 3 h

5: 98 percent / H₂ / 10percent Pd-C / ethyl acetate / 16 h / 3000.2 Torr

6: 4-toluenesulfonic acid / acetonitrile / 0.5 h / Ambient temperature

7: pyridine, 4-dimethylaminopyridine / CH₂Cl₂ / 2 h

8: aq. trifluoracetic acid / acetonitrile / 0.5 h

With pyridine; dmap; N-iodo-succinimide; sulfuric acid; boron trifluoride diethyl etherate; hydrogen; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; trifluoroacetic acid; zinc(II) chloride; palladium on activated charcoal; In pyridine; dichloromethane; acetic acid; ethyl acetate; acetonitrile;

DOI:10.1016/S0008-6215(00)90553-6

Reference yield:

2-[4-(trifluoroacetylamino)phenyl]ethanol (115166-92-2) → 2-(4-trifluoroacetamidophenyl)ethyl 2,6,7-tri-O-acetyl-4-O-chloroacetyl-L-glycero-α-D-manno-heptopyranoside (142270-26-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) silver triflate, N-iodosuccinimide, 2) BF₃-etherate / 1) CH₂Cl₂, CH₃CN, 10 min, 2) CH₃CN, 3 h

2: 98 percent / H₂ / 10percent Pd-C / ethyl acetate / 16 h / 3000.2 Torr

3: 4-toluenesulfonic acid / acetonitrile / 0.5 h / Ambient temperature

4: pyridine, 4-dimethylaminopyridine / CH₂Cl₂ / 2 h

5: aq. trifluoracetic acid / acetonitrile / 0.5 h

With pyridine; dmap; N-iodo-succinimide; boron trifluoride diethyl etherate; hydrogen; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1016/S0008-6215(00)90553-6

Reference yield:

ethyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside (142270-23-3) → 2-(4-trifluoroacetamidophenyl)ethyl 2,6,7-tri-O-acetyl-4-O-chloroacetyl-L-glycero-α-D-manno-heptopyranoside (142270-26-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) silver triflate, N-iodosuccinimide, 2) BF₃-etherate / 1) CH₂Cl₂, CH₃CN, 10 min, 2) CH₃CN, 3 h

2: 98 percent / H₂ / 10percent Pd-C / ethyl acetate / 16 h / 3000.2 Torr

3: 4-toluenesulfonic acid / acetonitrile / 0.5 h / Ambient temperature

4: pyridine, 4-dimethylaminopyridine / CH₂Cl₂ / 2 h

5: aq. trifluoracetic acid / acetonitrile / 0.5 h

With pyridine; dmap; N-iodo-succinimide; boron trifluoride diethyl etherate; hydrogen; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1016/S0008-6215(00)90553-6

upstream raw materials:

methyl-2,3,4-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside

2-[4-(trifluoroacetylamino)phenyl]ethanol

2-(4-trifluoroacetamidophenyl)ethyl 6,7-di-O-acetyl-L-glycero-α-D-manno-heptopyranoside

methyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranoside

Downstream raw materials:

2-(4-trifluoroacetamidophenyl)ethyl O-<6-O-benzoyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranosyl>-(1-3)-2,6,7-tri-O-acetyl-4-O-chloroacetyl-L-glycero-α-D-manno-heptopyranoside

2-(4-Trifluoroacetamidophenyl)ethyl 3-O-(6,7-di-O-acetyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranosyl)-2,6,7-tri-O-acetyl-4-O-chloroacetyl-L-glycero-α-D-manno-heptopyranoside

2-(4-trifluoroacetamidophenyl)ethyl O-<6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(tert-butyldimethylsilyl)-L-glycero-α-D-manno-heptopyranosyl>-(1-3)-2,6,7-tri-O-acetyl-4-O-chloroacetyl-L-glycero-α-D-manno-heptopyranoside