O--(2->6)-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)-(1->3)-N-(trichloroethoxycarbonyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)...

Base Information

• Chemical Name: O--(2->6)-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)-(1->3)-N-(trichloroethoxycarbonyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)...
• CAS No.: 197663-25-5
• Molecular Formula: C₄₈H₆₄Cl₃N₅O₂₅
• Molecular Weight: 1217.41

Synonyms:

Chemical Property of O--(2->6)-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)-(1->3)-N-(trichloroethoxycarbonyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)...

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O--(2->6)-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)-(1->3)-N-(trichloroethoxycarbonyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)...

There total 9 articles about O--(2->6)-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)-(1->3)-N-(trichloroethoxycarbonyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)... 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-di-O-acetyl-2-azido-6-O-triphenylmethyl-2-deoxy-1-thio-D-galactopyranoside (197663-20-0) → O--(2->6)-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)-(1->3)-N-(trichloroethoxycarbonyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)... (197663-25-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / NBS, I₂, tetrabutylammonium trifluoromethanesulfonate, 4A molecular sieves / diethyl ether / a) -20 deg C, 1 h, b) RT, 2 h

2: 66 percent / pyridine / CH₂Cl₂ / 8 h / Ambient temperature

3: 71 percent / 80 percent aq. AcOH / 6 h / 60 °C

4: 55 percent / NBS, I₂, tetrabutylammonium trifluoromethanesulfonate, 3 A molecular sieves / acetonitrile / 4 h / -40 °C

5: H₂ / Pd-black / methanol; tetrahydrofuran / 10 h / Ambient temperature

6: WSC*HCl, 1-hydroxy-1H-benzotriazole, Et₃N / CH₂Cl₂; methanol / a) 0 deg C, 1 h, b) RT, 20 h

With pyridine; N-Bromosuccinimide; 3 A molecular sieve; 4 A molecular sieve; WSC*HCl; hydrogen; iodine; tetrabutylammonium trifluoromethylsulfonate; benzotriazol-1-ol; acetic acid; triethylamine; palladium; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1248/cpb.46.1676

Reference yield:

N-trichloroethoxycarbonyl-3-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine benzyl ester (197663-23-3) → O--(2->6)-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)-(1->3)-N-(trichloroethoxycarbonyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)... (197663-25-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 55 percent / NBS, I₂, tetrabutylammonium trifluoromethanesulfonate, 3 A molecular sieves / acetonitrile / 4 h / -40 °C

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

3: WSC*HCl, 1-hydroxy-1H-benzotriazole, Et₃N / CH₂Cl₂; methanol / a) 0 deg C, 1 h, b) RT, 20 h

With N-Bromosuccinimide; 3 A molecular sieve; WSC*HCl; hydrogen; iodine; tetrabutylammonium trifluoromethylsulfonate; benzotriazol-1-ol; triethylamine; palladium; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1248/cpb.46.1676

Reference yield:

N-trichloroethoxycarbonyl-3-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-triphenylmethyl-α-D-galactopyranosyl)-L-serine benzyl ester (197663-22-2) → O--(2->6)-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)-(1->3)-N-(trichloroethoxycarbonyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)... (197663-25-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 71 percent / 80 percent aq. AcOH / 6 h / 60 °C

2: 55 percent / NBS, I₂, tetrabutylammonium trifluoromethanesulfonate, 3 A molecular sieves / acetonitrile / 4 h / -40 °C

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

4: WSC*HCl, 1-hydroxy-1H-benzotriazole, Et₃N / CH₂Cl₂; methanol / a) 0 deg C, 1 h, b) RT, 20 h

With N-Bromosuccinimide; 3 A molecular sieve; WSC*HCl; hydrogen; iodine; tetrabutylammonium trifluoromethylsulfonate; benzotriazol-1-ol; acetic acid; triethylamine; palladium; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1248/cpb.46.1676

upstream raw materials:

benzyl N-(2-aminoethyl)carbamate hydrochloride

benzyl N-(2,2,2-trichloroethoxycarbonyl)-L-serine

phenyl-3,4-di-O-acetyl-2-azido-6-O-triphenylmethyl-2-deoxy-1-thio-D-galactopyranoside

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

Downstream raw materials:

C₄₅H₆₃N₅O₂₃

O-<5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid-(2->6)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-N-(acetyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)amide

O--(2->6)-O-(2-acetamido-3,4-di-O-acetyl-2-deoxy-α-D-galactopyranosyl)-(1->3)-N-(acetyl)-L-serine-(N'-benzyloxycarbonylaminoethyl)amide

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