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

Base Information

• Chemical Name: N^δ-(5-tert-butyldiphenylsilyl-α-D-ribosyl)-N^α-benzyloxycarbonylasparagine benzyl ester
• CAS No.: 1461715-84-3
• Molecular Formula: C₄₀H₄₆N₂O₉Si
• Molecular Weight: 726.899

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

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

Chemical Property:

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

There total 2 articles about N^δ-(5-tert-butyldiphenylsilyl-α-D-ribosyl)-N^α-benzyloxycarbonylasparagine 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: 60.0%

5-tert-butyldiphenylsilyl-β-D-ribofuranosyl azide (1220340-25-9) + 1-benzyl 5-[2-(diphenylphosphanyl)-4-fluorophenyl]-N-(benzyloxycarbonyl)-L-aspartate (1461715-82-1) → Nδ-(5-tert-butyldiphenylsilyl-α-D-ribosyl)-Nα-benzyloxycarbonylasparagine benzyl ester (1461715-84-3)

Guidance literature:

5-tert-butyldiphenylsilyl-β-D-ribofuranosyl azide; 1-benzyl 5-[2-(diphenylphosphanyl)-4-fluorophenyl]-N-(benzyloxycarbonyl)-L-aspartate; 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:

Z-Asp-OBn (4779-31-1) → Nδ-(5-tert-butyldiphenylsilyl-α-D-ribosyl)-Nα-benzyloxycarbonylasparagine benzyl ester (1461715-84-3)

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-benzyloxycarbonylasparagine benzyl ester (1461715-84-3) + acetic anhydride (108-24-7) → Nγ-(5-tert-butyldiphenylsilyl-2,3-di-O-acetyl-α-D-ribosyl)-N-α-benzyloxycarbonyl asparagine benzyl ester (1220340-27-1)

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-aspartate

Z-Asp-OBn

Downstream raw materials:

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

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