methyl (2-acetamido-4-O-tert-butyldimethylsilyl-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-(2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranoside

Base Information

• Chemical Name: methyl (2-acetamido-4-O-tert-butyldimethylsilyl-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-(2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranoside
• CAS No.: 1363497-45-3
• Molecular Formula: C₅₅H₆₉N₃O₁₉Si
• Molecular Weight: 1104.25

Synonyms:methyl (2-acetamido-4-O-tert-butyldimethylsilyl-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-(2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranoside

Chemical Property of methyl (2-acetamido-4-O-tert-butyldimethylsilyl-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-(2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranoside

Chemical Property:

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Technology Process of methyl (2-acetamido-4-O-tert-butyldimethylsilyl-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-(2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranoside

There total 12 articles about methyl (2-acetamido-4-O-tert-butyldimethylsilyl-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-(2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranoside 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: 61.0%

para-tolyl 2-acetamido-4-O-tert-butyldimethylsilyl-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-α-D-galactopyranoside (1363497-23-7) + methyl (2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranoside (1363497-42-0) → methyl (2-acetamido-4-O-tert-butyldimethylsilyl-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-(2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranoside (1363497-45-3)

Guidance literature:

para-tolyl 2-acetamido-4-O-tert-butyldimethylsilyl-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-α-D-galactopyranoside; With trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -72 ℃; for 0.0833333h; Molecular sieve; Inert atmosphere;

methyl (2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranoside; In dichloromethane; at -72 - 20 ℃; for 2h; diastereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1002/chem.201102615

Reference yield:

p-tolyl 2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-α-D-galactopyranoside (1242060-81-6) → methyl (2-acetamido-4-O-tert-butyldimethylsilyl-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-(2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranoside (1363497-45-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 48 h / 70 °C

2.1: trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 0.08 h / -72 °C / Molecular sieve; Inert atmosphere

2.2: 2 h / -72 - 20 °C / Molecular sieve; Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C

4.1: trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 0.08 h / -72 °C / Molecular sieve; Inert atmosphere

4.2: 2 h / -72 - 20 °C / Molecular sieve; Inert atmosphere

With 1H-imidazole; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; tetrabutyl ammonium fluoride; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.201102615

Reference yield:

methyl (2-acetamido-4-O-tert-butyldimethylsilyl-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranoside (1363497-39-5) → methyl (2-acetamido-4-O-tert-butyldimethylsilyl-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-(2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranoside (1363497-45-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 20 °C

2.1: trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 0.08 h / -72 °C / Molecular sieve; Inert atmosphere

2.2: 2 h / -72 - 20 °C / Molecular sieve; Inert atmosphere

With trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; tetrabutyl ammonium fluoride; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/chem.201102615

upstream raw materials:

p-tolyl 2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-α-D-galactopyranoside

methyl 2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranoside

methyl (2-acetamido-4-O-tert-butyldimethylsilyl-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranoside

para-tolyl 2-acetamido-4-O-tert-butyldimethylsilyl-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-α-D-galactopyranoside

Downstream raw materials:

methyl (2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-(2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzyl-2,3-N,O-carbonyl-2-deoxy-α-D-galactopyranoside

methyl (2-acetamido-3,4-di-O-acetyl-6-O-benzyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-(2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-α-D-galactopyranosyl)-(1->4)-2-acetamido-3-O-acetyl-6-O-benzyl-2-deoxy-α-D-galactopyranoside

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