N-acetyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)amide

Base Information

• Chemical Name: N-acetyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)amide
• CAS No.: 197663-16-4
• Molecular Formula: C₂₉H₄₀N₄O₁₃
• Molecular Weight: 652.656
• Mol file: 197663-16-4.mol

Synonyms:N-acetyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)amide

Chemical Property of N-acetyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-acetyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)amide

There total 6 articles about N-acetyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)amide 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:

phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thiol-D-galactopyranoside (197663-12-0) → N-acetyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)amide (197663-16-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 65 percent / NBS, I₂, tetrabutylammonium trifluoromethanesulfonate, 4A molecular sieves / diethyl ether / a) -20 deg C, 1 h, b) RT, 2 h

2: 68 percent / pyridine / CH₂Cl₂ / 8 h / Ambient temperature

3: H₂ / Pd-black / tetrahydrofuran / 10 h / Ambient temperature

4: WSC*HCl, 1-hydroxy-1H-benzotriazole, Et₃N / dimethylformamide / a) 0 deg C, 1 h, b) RT, 20 h

5: Zn, AcOH / 18 h / 38 - 40 °C

6: pyridine, dimethylaminopyridine / CH₂Cl₂ / a) 0 deg C, 1 h, b) RT, 17 h

With pyridine; dmap; N-Bromosuccinimide; 4 A molecular sieve; WSC*HCl; hydrogen; iodine; tetrabutylammonium trifluoromethylsulfonate; benzotriazol-1-ol; acetic acid; triethylamine; zinc; palladium; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.46.1676

Reference yield:

N-trichloroethoxycarbonyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester (197663-14-2) → N-acetyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)amide (197663-16-4)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Pd-black / tetrahydrofuran / 10 h / Ambient temperature

2: WSC*HCl, 1-hydroxy-1H-benzotriazole, Et₃N / dimethylformamide / a) 0 deg C, 1 h, b) RT, 20 h

3: Zn, AcOH / 18 h / 38 - 40 °C

4: pyridine, dimethylaminopyridine / CH₂Cl₂ / a) 0 deg C, 1 h, b) RT, 17 h

With pyridine; dmap; WSC*HCl; hydrogen; benzotriazol-1-ol; acetic acid; triethylamine; zinc; palladium; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.46.1676

Reference yield:

N-trichloroethoxycarbonyl-3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester (197663-13-1) → N-acetyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)amide (197663-16-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / pyridine / CH₂Cl₂ / 8 h / Ambient temperature

2: H₂ / Pd-black / tetrahydrofuran / 10 h / Ambient temperature

3: WSC*HCl, 1-hydroxy-1H-benzotriazole, Et₃N / dimethylformamide / a) 0 deg C, 1 h, b) RT, 20 h

4: Zn, AcOH / 18 h / 38 - 40 °C

5: pyridine, dimethylaminopyridine / CH₂Cl₂ / a) 0 deg C, 1 h, b) RT, 17 h

With pyridine; dmap; WSC*HCl; hydrogen; benzotriazol-1-ol; acetic acid; triethylamine; zinc; palladium; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.46.1676

upstream raw materials:

phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thiol-D-galactopyranoside

N-trichloroethoxycarbonyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester

N-trichloroethoxycarbonyl-3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester

N-trichloroethoxycarbonyl-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-seryl-(N'-benzyloxycarbonylaminoethyl)amide

Downstream raw materials:

N-acetyl-3-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)amide