N^α-benzyloxycarbonyl-N^γ-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-asparagine-O-methyl ester

Base Information

• Chemical Name: N^α-benzyloxycarbonyl-N^γ-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-asparagine-O-methyl ester
• CAS No.: 848863-25-2
• Molecular Formula: C₄₇H₅₀N₂O₁₀
• Molecular Weight: 802.921

Synonyms:N^α-benzyloxycarbonyl-N^γ-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-asparagine-O-methyl ester

Chemical Property of N^α-benzyloxycarbonyl-N^γ-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-asparagine-O-methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of N^α-benzyloxycarbonyl-N^γ-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-asparagine-O-methyl ester

There total 3 articles about N^α-benzyloxycarbonyl-N^γ-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-asparagine-O-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:

1-azido-1-deoxy-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose (85917-82-4) + N-benzyloxycarbonyl-L-aspartic acid 4-(2-diphenylphosphanyl-phenyl) ester 1-methyl ester (848863-20-7) → Nα-benzyloxycarbonyl-Nγ-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-asparagine-O-methyl ester + Nα-benzyloxycarbonyl-Nγ-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-asparagine-O-methyl ester (848863-25-2)

Guidance literature:

1-azido-1-deoxy-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose; N-benzyloxycarbonyl-L-aspartic acid 4-(2-diphenylphosphanyl-phenyl) ester 1-methyl ester; In toluene; at 70 ℃; for 1h;

In chloroform; at 20 ℃; Title compound not separated from byproducts;

DOI:10.1016/j.tetasy.2004.11.055

Reference yield:

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose (80300-30-7) → Nα-benzyloxycarbonyl-Nγ-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-asparagine-O-methyl ester (848863-25-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trimethylsilyl azide / tin tetrachloride / CH₂Cl₂ / 1 h / 20 °C

2.1: N,N-dimethyl-acetamide; toluene / 4 h / 70 °C

2.2: water / N,N-dimethyl-acetamide; toluene / 18 h / 70 °C

With trimethylsilylazide; tin(IV) chloride; In dichloromethane; N,N-dimethyl acetamide; toluene; 2.1: Staudinger ligation / 2.2: Staudinger ligation;

DOI:10.1021/jo060409s

Reference yield:

(S)-2-benzyloxycarbonylamino-succinic acid 1-methyl ester (4668-42-2) → Nα-benzyloxycarbonyl-Nγ-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-asparagine-O-methyl ester (848863-25-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 85 percent / N,N-dimethylaminopyridine; N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride; N,N-diisopropylethylamine / CH₂Cl₂ / 2 h / 20 °C

2.1: N,N-dimethyl-acetamide; toluene / 4 h / 70 °C

2.2: water / N,N-dimethyl-acetamide; toluene / 18 h / 70 °C

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl acetamide; toluene; 2.1: Staudinger ligation / 2.2: Staudinger ligation;

DOI:10.1021/jo060409s

upstream raw materials:

1-azido-1-deoxy-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose

N-benzyloxycarbonyl-L-aspartic acid 4-(2-diphenylphosphanyl-phenyl) ester 1-methyl ester

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose

(S)-2-benzyloxycarbonylamino-succinic acid 1-methyl ester

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