Nα-(benzyloxycarbonyl)-Nδ-(β-D-glucopyranosyl)-L-glutamine O-methyl ester

Base Information

• Chemical Name: Nα-(benzyloxycarbonyl)-Nδ-(β-D-glucopyranosyl)-L-glutamine O-methyl ester
• CAS No.: 1046453-81-9
• Molecular Formula: C₂₀H₂₈N₂O₁₀
• Molecular Weight: 456.45

Synonyms:Nα-(benzyloxycarbonyl)-Nδ-(β-D-glucopyranosyl)-L-glutamine O-methyl ester

Chemical Property of Nα-(benzyloxycarbonyl)-Nδ-(β-D-glucopyranosyl)-L-glutamine O-methyl ester

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Technology Process of Nα-(benzyloxycarbonyl)-Nδ-(β-D-glucopyranosyl)-L-glutamine O-methyl ester

There total 2 articles about Nα-(benzyloxycarbonyl)-Nδ-(β-D-glucopyranosyl)-L-glutamine 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: 87.0%

D-glucopyranosyl azide (20379-59-3) + 1-methyl 5-[2-(diphenylphosphanyl)-4-fluorophenyl] N-(benzyloxycarbonyl)-L-glutamate (1202249-75-9) → Nα-(benzyloxycarbonyl)-Nδ-(β-D-glucopyranosyl)-L-glutamine O-methyl ester (1046453-81-9)

Guidance literature:

D-glucopyranosyl azide; 1-methyl 5-[2-(diphenylphosphanyl)-4-fluorophenyl] N-(benzyloxycarbonyl)-L-glutamate; In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N-dimethyl acetamide; at 20 - 40 ℃; Inert atmosphere;

With water; In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N-dimethyl acetamide; at 40 ℃; for 2h;

DOI:10.1002/ejoc.200900692

Reference yield: 38.0%

D-glucopyranosyl azide (20379-59-3) + N-benzyloxycarbonyl-L-glutamic acid 5-(2-diphenylphosphanyl-phenyl)ester 1-methyl ester (1046453-70-6) → Nα-(benzyloxycarbonyl)-Nδ-(β-D-glucopyranosyl)-L-glutamine O-methyl ester (1046453-81-9)

Guidance literature:

D-glucopyranosyl azide; N-benzyloxycarbonyl-L-glutamic acid 5-(2-diphenylphosphanyl-phenyl)ester 1-methyl ester; In N,N-dimethyl acetamide; at 50 ℃; for 0.833333h; microwave irradiation;

With water; In N,N-dimethyl acetamide; at 50 ℃; for 0.25h; Further stages.; microwave irradiation;

DOI:10.1016/j.carres.2008.04.023

Reference yield: 100.0%

Nα-(benzyloxycarbonyl)-Nδ-(β-D-glucopyranosyl)-L-glutamine O-methyl ester (1046453-81-9) + acetic anhydride (108-24-7) → Nα-(benzyloxycarbonyl)-Nδ-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-glutamine O-methyl ester (1202249-95-3)

Guidance literature:

With pyridine; dmap; at 20 ℃;

DOI:10.1002/ejoc.200900692

upstream raw materials:

D-glucopyranosyl azide

N-benzyloxycarbonyl-L-glutamic acid 5-(2-diphenylphosphanyl-phenyl)ester 1-methyl ester

1-methyl 5-[2-(diphenylphosphanyl)-4-fluorophenyl] N-(benzyloxycarbonyl)-L-glutamate

Downstream raw materials:

Nα-(benzyloxycarbonyl)-Nδ-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-L-glutamine O-methyl ester

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