N^α-tert-butoxycarbonyl-N⁵-(5'-deoxy-5'-uridyl)-L-isoglutamine benzyl ester

Base Information

• Chemical Name: N^α-tert-butoxycarbonyl-N⁵-(5'-deoxy-5'-uridyl)-L-isoglutamine benzyl ester
• CAS No.: 174838-39-2
• Molecular Formula: C₂₆H₃₄N₄O₁₀
• Molecular Weight: 562.577
• Mol file: 174838-39-2.mol

Synonyms:N^α-tert-butoxycarbonyl-N⁵-(5'-deoxy-5'-uridyl)-L-isoglutamine benzyl ester

Chemical Property of N^α-tert-butoxycarbonyl-N⁵-(5'-deoxy-5'-uridyl)-L-isoglutamine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N^α-tert-butoxycarbonyl-N⁵-(5'-deoxy-5'-uridyl)-L-isoglutamine benzyl ester

There total 1 articles about N^α-tert-butoxycarbonyl-N⁵-(5'-deoxy-5'-uridyl)-L-isoglutamine 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: 88.0%

Boc-Glu(OBzl)-OH (13574-13-5) + 5'-amino-5'-deoxyuridine (24514-44-1,34718-92-8,71295-94-8) → Nα-tert-butoxycarbonyl-N5-(5'-deoxy-5'-uridyl)-L-isoglutamine benzyl ester (174838-39-2)

Guidance literature:

Boc-Glu(OBzl)-OH; With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 ℃; for 0.00833333h;

5'-amino-5'-deoxyuridine; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1021/ja9935456

Reference yield: 98.0%

trifluoroacetic acid (76-05-1) + Nα-tert-butoxycarbonyl-N5-(5'-deoxy-5'-uridyl)-L-isoglutamine benzyl ester (174838-39-2) → N5-(5'-deoxy-5'-uridyl)-L-isoglutamine benzyl ester trifluoroacetic acid salt

Guidance literature:

at 0 ℃; for 0.5h;

DOI:10.1021/ja9935456

Reference yield:

Nα-tert-butoxycarbonyl-N5-(5'-deoxy-5'-uridyl)-L-isoglutamine benzyl ester (174838-39-2) → C40H51N9O17

Guidance literature:

Multi-step reaction with 3 steps

1.1: 95 percent / H₂ / 10 percent Pd/C / methanol / 2 h / 20 °C / 760 Torr

2.1: BOP; HOBt; diisopropylethylamine / dimethylformamide / 0.01 h / 0 °C

2.2: 98 percent / dimethylformamide / 2 h / 20 °C

3.1: H₂ / 10 percent Pd/C / methanol / 20 °C

With hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide; 1.1: Hydrogenolysis / 2.1: activation / 3.1: Hydrogenolysis;

DOI:10.1021/ja9935456

upstream raw materials:

Boc-Glu(OBzl)-OH

5'-amino-5'-deoxyuridine

Downstream raw materials:

Boc-(isoGln(5'U))2-OBzl

Boc-isoGln(5'U)-isoGln(5'BzC)-OBzl