N^δ-(5-tert-butyldiphenylsilyl-α-D-ribosyl)-N^α-benzyloxycarbonylglutamine benzyl ester

Base Information

• Chemical Name: N^δ-(5-tert-butyldiphenylsilyl-α-D-ribosyl)-N^α-benzyloxycarbonylglutamine benzyl ester
• CAS No.: 1461715-85-4
• Molecular Formula: C₄₁H₄₈N₂O₉Si
• Molecular Weight: 740.926

Synonyms:N^δ-(5-tert-butyldiphenylsilyl-α-D-ribosyl)-N^α-benzyloxycarbonylglutamine benzyl ester

Chemical Property of N^δ-(5-tert-butyldiphenylsilyl-α-D-ribosyl)-N^α-benzyloxycarbonylglutamine benzyl ester

Chemical Property:

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Technology Process of N^δ-(5-tert-butyldiphenylsilyl-α-D-ribosyl)-N^α-benzyloxycarbonylglutamine benzyl ester

There total 2 articles about N^δ-(5-tert-butyldiphenylsilyl-α-D-ribosyl)-N^α-benzyloxycarbonylglutamine 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: 76.0%

5-tert-butyldiphenylsilyl-β-D-ribofuranosyl azide (1220340-25-9) + 1-benzyl 5-[2-(diphenylphosphanyl)-4-fluorophenyl]-N-(benzyloxycarbonyl)-L-glutamate (1461715-83-2) → Nδ-(5-tert-butyldiphenylsilyl-α-D-ribosyl)-Nα-benzyloxycarbonylglutamine benzyl ester (1461715-85-4)

Guidance literature:

5-tert-butyldiphenylsilyl-β-D-ribofuranosyl azide; 1-benzyl 5-[2-(diphenylphosphanyl)-4-fluorophenyl]-N-(benzyloxycarbonyl)-L-glutamate; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N-dimethyl acetamide; at 20 - 70 ℃; for 20h;

With water; at 70 ℃; for 2h; stereoselective reaction;

DOI:10.3390/molecules18088779

Reference yield:

Cbz-(L)-Glu-OBn (3705-42-8) → Nδ-(5-tert-butyldiphenylsilyl-α-D-ribosyl)-Nα-benzyloxycarbonylglutamine benzyl ester (1461715-85-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

2.1: 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N-dimethyl acetamide / 20 h / 20 - 70 °C

2.2: 2 h / 70 °C

With dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; N,N-dimethyl acetamide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.3390/molecules18088779

Reference yield:

Nδ-(5-tert-butyldiphenylsilyl-α-D-ribosyl)-Nα-benzyloxycarbonylglutamine benzyl ester (1461715-85-4) + acetic anhydride (108-24-7) → Nδ-(5-tert-butyldiphenylsilyl-2,3-di-O-acetyl-α-D-ribosyl)-N-α-benzyloxycarbonyl glutamine benzyl ester (1220340-28-2)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 24h;

DOI:10.3390/molecules18088779

upstream raw materials:

5-tert-butyldiphenylsilyl-β-D-ribofuranosyl azide

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

Cbz-(L)-Glu-OBn

Downstream raw materials:

Nδ-(5-tert-butyldiphenylsilyl-2,3-di-O-acetyl-α-D-ribosyl)-N-α-benzyloxycarbonyl glutamine benzyl ester

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