N(benzyl 2-acetamido-4,6-O-benzylidene-2,3-dideoxy-α-D-glucopyranosid-3-yl)-L-alanyl-L-alanyl-D-isoglutamine methyl ester

Base Information

• Chemical Name: N(benzyl 2-acetamido-4,6-O-benzylidene-2,3-dideoxy-α-D-glucopyranosid-3-yl)-L-alanyl-L-alanyl-D-isoglutamine methyl ester
• CAS No.: 108432-67-3
• Molecular Formula: C₃₄H₄₅N₅O₁₀
• Molecular Weight: 683.759
• Mol file: 108432-67-3.mol

Synonyms:

Chemical Property of N(benzyl 2-acetamido-4,6-O-benzylidene-2,3-dideoxy-α-D-glucopyranosid-3-yl)-L-alanyl-L-alanyl-D-isoglutamine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N(benzyl 2-acetamido-4,6-O-benzylidene-2,3-dideoxy-α-D-glucopyranosid-3-yl)-L-alanyl-L-alanyl-D-isoglutamine methyl ester

There total 8 articles about N(benzyl 2-acetamido-4,6-O-benzylidene-2,3-dideoxy-α-D-glucopyranosid-3-yl)-L-alanyl-L-alanyl-D-isoglutamine methyl ester 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: 70.0%

L-alanyl-D-isoglutamine methyl ester trifluoroacetate (88815-72-9) + benzyl 2-acetamido-4,6-O-benzylidene-3-<amino>-2,3-dideoxy-α-D-glucopyranoside (108432-64-0,108432-66-2) → N(benzyl 2-acetamido-4,6-O-benzylidene-2,3-dideoxy-α-D-glucopyranosid-3-yl)-L-alanyl-L-alanyl-D-isoglutamine methyl ester (108432-67-3,108508-15-2)

Guidance literature:

With 1-hydroxy-pyrrolidine-2,5-dione; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1.) ice bath 3 h, room temperature 1 h;

DOI:10.1016/S0040-4020(01)87561-X

Reference yield:

benzyl 2-acetamido-3-amino-4,6-O-benzylidene-2,3-dideoxy-α-D-glucopyranoside (53910-43-3,61330-53-8,107983-28-8) → N-(benzyl 2-acetamido-4,6-O-benzylidene-2,3-dideoxy-α-D-glucopyranosid-3-yl)-D-alanyl-L-alanyl-D-isoglutamine methyl ester (108432-67-3,108508-15-2)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / acetonitrile / 20 h / Heating

2: 79 percent / 1.) 1percent KOH / Ambient temperature; 1.) ethanol, 20 h, 2.) water, Amberlite IRC-50(H⁺)

3: 1.) N-hydroxysuccinimide, dicyclohexylcarbodiimide; 2.) triethylamine / 1.) THF, ice bath 3 h, room temperature 1 h; 2.) THF, ice-bath cooling

With pyridine; potassium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; triethylamine; dicyclohexyl-carbodiimide; In acetonitrile;

DOI:10.1016/S0040-4020(01)87561-X

Reference yield:

benzyl 2-acetamido-3-amino-4,6-O-benzylidene-2,3-dideoxy-α-D-glucopyranoside (53910-43-3,61330-53-8,107983-28-8) → N(benzyl 2-acetamido-4,6-O-benzylidene-2,3-dideoxy-α-D-glucopyranosid-3-yl)-L-alanyl-L-alanyl-D-isoglutamine methyl ester (108432-67-3,108508-15-2)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / acetonitrile / 20 h / Heating

2: 77 percent / 1.) 1percent KOH / Ambient temperature; 1.) ethanol, 20 deg C, 2.) water, Amberlite IRC-50(H⁺)

3: 70 percent / 1.) N-hydroxsuccinimide, dicyclohexylcarbodiimide; 2.) triethylamine / tetrahydrofuran / 1.) ice bath 3 h, room temperature 1 h

With pyridine; potassium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; acetonitrile;

DOI:10.1016/S0040-4020(01)87561-X

upstream raw materials:

L-alanyl-D-isoglutamine methyl ester trifluoroacetate

benzyl 2-acetamido-4,6-O-benzylidene-3-<amino>-2,3-dideoxy-α-D-glucopyranoside

methyl 2-acetamido-3-amino-4,6-O-bezylidene-2,3-dideoxy-α-D-glucopyranoside

benzyl 2-acetamido-3-amino-4,6-O-benzylidene-2,3-dideoxy-α-D-glucopyranoside