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

Base Information

Chemical Name:N-acetyl-3-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)amide
CAS No.:197663-17-5
Molecular Formula:C₂₃H₃₄N₄O₁₀
Molecular Weight:526.544
Hs Code.:

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

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

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

There total 8 articles about N-acetyl-3-O-(2-acetamido-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: 92.0%

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

: 197663-17-5
N-acetyl-3-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)amide

Guidance literature:: With potassium hydroxide; In methanol; at 0 ℃; for 2h;
DOI:10.1248/cpb.45.1544

Reference yield:

: 197663-12-0
phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thiol-D-galactopyranoside

: 197663-17-5
N-acetyl-3-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)amide

Guidance literature:: Multi-step reaction with 7 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

7: 0.1 N KOH / methanol / a) 0 deg C, 2 h, b) RT, 1 h

With pyridine; dmap; potassium hydroxide; N-Bromosuccinimide; 4 A molecular sieve; WSC*HCl; hydrogen; iodine; tetrabutylammonium trifluoromethylsulfonate; benzotriazol-1-ol; acetic acid; triethylamine; zinc; palladium; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.46.1676

Reference yield:

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

: 197663-17-5
N-acetyl-3-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)amide

Guidance literature:: Multi-step reaction with 5 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

5: 0.1 N KOH / methanol / a) 0 deg C, 2 h, b) RT, 1 h

With pyridine; dmap; potassium hydroxide; WSC*HCl; hydrogen; benzotriazol-1-ol; acetic acid; triethylamine; zinc; palladium; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.46.1676