N^α-<4-<(<2,4-diamino-6-pteridinyl>methyl)methylamino>benzoyl>-N^δ-<2,2-bis(diethylphosphono)ethyl>glutamine ethyl ester

Base Information

• Chemical Name: N^α-<4-<(<2,4-diamino-6-pteridinyl>methyl)methylamino>benzoyl>-N^δ-<2,2-bis(diethylphosphono)ethyl>glutamine ethyl ester
• CAS No.: 147938-31-6
• Molecular Formula: C₃₂H₄₉N₉O₁₀P₂
• Molecular Weight: 781.743

Synonyms:N^α-<4-<(<2,4-diamino-6-pteridinyl>methyl)methylamino>benzoyl>-N^δ-<2,2-bis(diethylphosphono)ethyl>glutamine ethyl ester

Chemical Property of N^α-<4-<(<2,4-diamino-6-pteridinyl>methyl)methylamino>benzoyl>-N^δ-<2,2-bis(diethylphosphono)ethyl>glutamine ethyl ester

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Technology Process of N^α-<4-<(<2,4-diamino-6-pteridinyl>methyl)methylamino>benzoyl>-N^δ-<2,2-bis(diethylphosphono)ethyl>glutamine ethyl ester

There total 6 articles about N^α-<4-<(<2,4-diamino-6-pteridinyl>methyl)methylamino>benzoyl>-N^δ-<2,2-bis(diethylphosphono)ethyl>glutamine ethyl 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: 70.0%

6-bromomethyl-2,4-diaminopteridine hydrobromide (52853-40-4) + Nα-<4-(methylamino)benzoyl>-Nδ-<2,2-bis(diethylphosphono)ethyl>glutamine ethyl ester (147938-30-5) → Nα-<4-<(<2,4-diamino-6-pteridinyl>methyl)methylamino>benzoyl>-Nδ-<2,2-bis(diethylphosphono)ethyl>glutamine ethyl ester (147938-31-6)

Guidance literature:

In N,N-dimethyl acetamide; at 50 ℃; for 4h;

DOI:10.1016/0223-5234(92)90117-J

Reference yield:

L-glutamine (56-85-9,26700-71-0) → Nα-<4-<(<2,4-diamino-6-pteridinyl>methyl)methylamino>benzoyl>-Nδ-<2,2-bis(diethylphosphono)ethyl>glutamine ethyl ester (147938-31-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / 1 N aq. NaOH / dioxane / 1 h / Ambient temperature

2: 94 percent / diisopropylethylamine / dioxane / 96 h / Ambient temperature

3: 90 percent / potassium tertiobutylate / 2-methyl-propan-2-ol / 1 h / 50 °C

4: 68 percent / triethylamine / tetrahydrofuran / 1 h / Ambient temperature

5: KH₂PO₄, Zn / H₂O / 24 h / Ambient temperature

6: 70 percent / N,N-dimethyl-acetamide / 4 h / 50 °C

With sodium hydroxide; potassium dihydrogenphosphate; potassium tert-butylate; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl acetamide; water; tert-butyl alcohol;

DOI:10.1016/0223-5234(92)90117-J

Reference yield:

Boc-Gln-OH (13726-85-7) → Nα-<4-<(<2,4-diamino-6-pteridinyl>methyl)methylamino>benzoyl>-Nδ-<2,2-bis(diethylphosphono)ethyl>glutamine ethyl ester (147938-31-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / diisopropylethylamine / dioxane / 96 h / Ambient temperature

2: 90 percent / potassium tertiobutylate / 2-methyl-propan-2-ol / 1 h / 50 °C

3: 68 percent / triethylamine / tetrahydrofuran / 1 h / Ambient temperature

4: KH₂PO₄, Zn / H₂O / 24 h / Ambient temperature

5: 70 percent / N,N-dimethyl-acetamide / 4 h / 50 °C

With potassium dihydrogenphosphate; potassium tert-butylate; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl acetamide; water; tert-butyl alcohol;

DOI:10.1016/0223-5234(92)90117-J

upstream raw materials:

6-bromomethyl-2,4-diaminopteridine hydrobromide

N^α-<4-(methylamino)benzoyl>-N^δ-<2,2-bis(diethylphosphono)ethyl>glutamine ethyl ester

L-glutamine

Boc-Gln-OH

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