benzyl 2-acetamido-4-O-<2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: benzyl 2-acetamido-4-O-<2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside
• CAS No.: 75957-47-0
• Molecular Formula: C₅₈H₇₃N₅O₁₆
• Molecular Weight: 1096.24
• Mol file: 75957-47-0.mol

Synonyms:benzyl 2-acetamido-4-O-<2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Chemical Property of benzyl 2-acetamido-4-O-<2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-acetamido-4-O-<2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

There total 6 articles about benzyl 2-acetamido-4-O-<2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 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:

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) → benzyl 2-acetamido-4-O-<2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (75957-47-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 30.4 percent / p-TsOH / 1,2-dichloro-ethane / 20 h / Heating

2: 333 mg / sodium methoxide / methanol

3: 82 percent / p-TsOH*H₂O / dimethylformamide / 2 h / 50 °C

4: 1.) sodium hydride / 1.) 1,4-dioxane, 95 deg C, 1.5 h; 2.) 1,4-dioxane, 65 deg C, 3 h

5: 1.) N-hydroxylsuccinimide, dicyclohexylcarbodiimide; 2.) triethylamine / 1.) 1,4-dioxane, room temperature, 2.5 h; 2.) 1,4-dioxane, room temperature, 2 h

With 1-hydroxy-pyrrolidine-2,5-dione; sodium methylate; sodium hydride; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; In methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)82587-2

Reference yield:

2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline (10378-06-0,20757-53-3,35954-65-5,123483-77-2,134308-33-1) → benzyl 2-acetamido-4-O-<2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (75957-47-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 30.4 percent / p-TsOH / 1,2-dichloro-ethane / 20 h / Heating

2: 333 mg / sodium methoxide / methanol

3: 82 percent / p-TsOH*H₂O / dimethylformamide / 2 h / 50 °C

4: 1.) sodium hydride / 1.) 1,4-dioxane, 95 deg C, 1.5 h; 2.) 1,4-dioxane, 65 deg C, 3 h

5: 1.) N-hydroxylsuccinimide, dicyclohexylcarbodiimide; 2.) triethylamine / 1.) 1,4-dioxane, room temperature, 2.5 h; 2.) 1,4-dioxane, room temperature, 2 h

With 1-hydroxy-pyrrolidine-2,5-dione; sodium methylate; sodium hydride; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; In methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)82587-2

Reference yield:

benzyl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (73821-90-6) → benzyl 2-acetamido-4-O-<2-acetamido-2-deoxy-4,6-O-isopropylidene-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine benzyl ester)-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (75957-47-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / p-TsOH*H₂O / dimethylformamide / 2 h / 50 °C

2: 1.) sodium hydride / 1.) 1,4-dioxane, 95 deg C, 1.5 h; 2.) 1,4-dioxane, 65 deg C, 3 h

3: 1.) N-hydroxylsuccinimide, dicyclohexylcarbodiimide; 2.) triethylamine / 1.) 1,4-dioxane, room temperature, 2.5 h; 2.) 1,4-dioxane, room temperature, 2 h

With 1-hydroxy-pyrrolidine-2,5-dione; sodium hydride; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)82587-2

upstream raw materials:

(S)-1-(((R)-1-amino-5-(benzyloxy)-1,5-dioxopentan-2-yl)amino)-1-oxopropan-2-aminium 2,2,2-trifluoroacetate

benzyl 2-acetamido-4-O-<2-acetamido-3-O-(D-1-carboxyethyl)-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline

Downstream raw materials:

C₅₅H₆₉N₅O₁₆

Refernces