methyl 4-O-acetyl-2,3-di-O-benzyl-D-galactopyranosiduronate 1-N-phenyltrifluoroacetimidate

Base Information

• Chemical Name: methyl 4-O-acetyl-2,3-di-O-benzyl-D-galactopyranosiduronate 1-N-phenyltrifluoroacetimidate
• CAS No.: 1448254-97-4
• Molecular Formula: C₃₁H₃₀F₃NO₈
• Molecular Weight: 601.576
• Mol file: 1448254-97-4.mol

Synonyms:methyl 4-O-acetyl-2,3-di-O-benzyl-D-galactopyranosiduronate 1-N-phenyltrifluoroacetimidate

Chemical Property of methyl 4-O-acetyl-2,3-di-O-benzyl-D-galactopyranosiduronate 1-N-phenyltrifluoroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-O-acetyl-2,3-di-O-benzyl-D-galactopyranosiduronate 1-N-phenyltrifluoroacetimidate

There total 11 articles about methyl 4-O-acetyl-2,3-di-O-benzyl-D-galactopyranosiduronate 1-N-phenyltrifluoroacetimidate 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: 87.0%

2,2,2-trifluoro-N-phenyl-acetimidoyl chloride (61881-19-4) + methyl 4-O-acetyl-2,3-di-O-benzyl-α/β-D-galactopyranuronate → methyl 4-O-acetyl-2,3-di-O-benzyl-D-galactopyranosiduronate 1-N-phenyltrifluoroacetimidate (1448254-97-4)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 2h;

DOI:10.1016/j.carres.2013.05.008

Reference yield:

C21H24O7 → methyl 4-O-acetyl-2,3-di-O-benzyl-D-galactopyranosiduronate 1-N-phenyltrifluoroacetimidate (1448254-97-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium hydrogencarbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2.1: dichloromethane / 0.17 h / 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: acetic acid; sulfuric acid / 3 h / 0 °C

4.1: ammonia / methanol; tetrahydrofuran / 0.33 h / 0 °C

5.1: potassium carbonate / acetone / 2 h / 20 °C

With sulfuric acid; ammonia; tetra-(n-butyl)ammonium iodide; potassium carbonate; potassium hydrogencarbonate; acetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.carres.2013.05.008

Reference yield:

methyl 2,3-di-O-benzyl-α-D-galactopyranoside (29388-46-3) → methyl 4-O-acetyl-2,3-di-O-benzyl-D-galactopyranosiduronate 1-N-phenyltrifluoroacetimidate (1448254-97-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 20 °C

2.1: potassium hydrogencarbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

3.1: dichloromethane / 0.17 h / 20 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

4.1: acetic acid; sulfuric acid / 3 h / 0 °C

5.1: ammonia / methanol; tetrahydrofuran / 0.33 h / 0 °C

6.1: potassium carbonate / acetone / 2 h / 20 °C

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sulfuric acid; ammonia; tetra-(n-butyl)ammonium iodide; potassium carbonate; potassium hydrogencarbonate; acetic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.carres.2013.05.008

upstream raw materials:

methyl 2,3-di-O-benzyl-α-D-galactopyranoside

methyl (methyl 2,3-di-O-benzyl-α-D-galactopyranosid)uronate

2,2,2-trifluoro-N-phenyl-acetimidoyl chloride

methyl 2,3-di-O-benzyl-4,6-O-((4-methoxyphenyl)methylene)-α-D-galactopyranoside

Downstream raw materials:

allyl (methyl 4-O-acetyl-2,3-di-O-benzyl-α-D-galactopyranosyluronate)-(1→2)-[2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1→4)]-3-O-benzyl-α-L-rhamnopyranoside