N^α-t-butoxycarbonyl-N^γ-(2,3,4,5-tetra-O-benzyl-α-D-glucopyranosyl)-L-asparagine-O-benzyl ester

Base Information

• Chemical Name: N^α-t-butoxycarbonyl-N^γ-(2,3,4,5-tetra-O-benzyl-α-D-glucopyranosyl)-L-asparagine-O-benzyl ester
• CAS No.: 898561-74-5
• Molecular Formula: C₅₀H₅₆N₂O₁₀
• Molecular Weight: 845.002

Synonyms:N^α-t-butoxycarbonyl-N^γ-(2,3,4,5-tetra-O-benzyl-α-D-glucopyranosyl)-L-asparagine-O-benzyl ester

Chemical Property of N^α-t-butoxycarbonyl-N^γ-(2,3,4,5-tetra-O-benzyl-α-D-glucopyranosyl)-L-asparagine-O-benzyl ester

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Technology Process of N^α-t-butoxycarbonyl-N^γ-(2,3,4,5-tetra-O-benzyl-α-D-glucopyranosyl)-L-asparagine-O-benzyl ester

There total 2 articles about N^α-t-butoxycarbonyl-N^γ-(2,3,4,5-tetra-O-benzyl-α-D-glucopyranosyl)-L-asparagine-O-benzyl 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-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose (80300-30-7) → Nα-t-butoxycarbonyl-Nγ-(2,3,4,5-tetra-O-benzyl-α-D-glucopyranosyl)-L-asparagine-O-benzyl ester (898561-74-5)

Guidance literature:

Multi-step reaction with 2 steps

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

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

2.2: water / toluene; N,N-dimethyl-acetamide / 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:

N-t-butoxycarbonyl-L-aspartic acid 4-(2-diphenylphosphanyl-phenyl) ester 1-benzyl ester (898561-90-5) + 1-azido-1-deoxy-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose (85917-82-4) → Nα-t-butoxycarbonyl-Nγ-(2,3,4,5-tetra-O-benzyl-β-D-glucopyranosyl)-L-asparagine-O-benzyl ester + Nα-t-butoxycarbonyl-Nγ-(2,3,4,5-tetra-O-benzyl-α-D-glucopyranosyl)-L-asparagine-O-benzyl ester (898561-74-5)

Guidance literature:

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

With water; In N,N-dimethyl acetamide; toluene; at 70 ℃; for 18h;

DOI:10.1021/jo060409s

upstream raw materials:

N-t-butoxycarbonyl-L-aspartic acid 4-(2-diphenylphosphanyl-phenyl) ester 1-benzyl ester

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

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

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