N²-Boc-N⁵-xanthyl-L-glutaminyl-O-L-lactyl-L-prolyl-N-methyl-D-leucine benzyl ester

Base Information

• Chemical Name: N²-Boc-N⁵-xanthyl-L-glutaminyl-O-L-lactyl-L-prolyl-N-methyl-D-leucine benzyl ester
• CAS No.: 291772-86-6
• Molecular Formula: C₄₅H₅₆N₄O₁₀
• Molecular Weight: 812.96

Synonyms:N²-Boc-N⁵-xanthyl-L-glutaminyl-O-L-lactyl-L-prolyl-N-methyl-D-leucine benzyl ester

Chemical Property of N²-Boc-N⁵-xanthyl-L-glutaminyl-O-L-lactyl-L-prolyl-N-methyl-D-leucine benzyl ester

Chemical Property:

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Technology Process of N²-Boc-N⁵-xanthyl-L-glutaminyl-O-L-lactyl-L-prolyl-N-methyl-D-leucine benzyl ester

There total 6 articles about N²-Boc-N⁵-xanthyl-L-glutaminyl-O-L-lactyl-L-prolyl-N-methyl-D-leucine 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: 87.0%

Nα-t-butoxycarbonyl-Nδ-xanthydryl-L-glutamine (55260-24-7) + L-lactyl-L-prolyl-N-methyl-D-leucine benzyl ester (291772-85-5) → N2-Boc-N5-xanthyl-L-glutaminyl-O-L-lactyl-L-prolyl-N-methyl-D-leucine benzyl ester (291772-86-6)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo000253a

Reference yield:

methyl (2R)-4-methyl-2-(methylamino)pentanoate (117710-31-3) → N2-Boc-N5-xanthyl-L-glutaminyl-O-L-lactyl-L-prolyl-N-methyl-D-leucine benzyl ester (291772-86-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / BOP-Cl; NMM / CH₂Cl₂ / -15 - 0 °C

2: 98 percent / H₂ / 10percent Pd/C / methanol; ethyl acetate / 3 h

3: 77 percent / 0.2 M LiOH / tetrahydrofuran; methanol; H₂O / 20 °C

4: 94 percent / K₂CO₃; Bu₄NI / dimethylformamide / 1 h / 20 °C

5: 87 percent / DCC; DMAP / CH₂Cl₂ / 0 - 20 °C

With 4-methyl-morpholine; dmap; lithium hydroxide; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; tetra-(n-butyl)ammonium iodide; potassium carbonate; dicyclohexyl-carbodiimide; 10percent Pd/C; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 1: Acylation / 2: Hydrogenolysis / 3: Hydrolysis / 4: Alkylation / 5: Acylation;

DOI:10.1021/jo000253a

Reference yield:

Bzl-(S)-Lac-(S)-Pro-OH (118171-92-9) → N2-Boc-N5-xanthyl-L-glutaminyl-O-L-lactyl-L-prolyl-N-methyl-D-leucine benzyl ester (291772-86-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / BOP-Cl; NMM / CH₂Cl₂ / -15 - 0 °C

2: 98 percent / H₂ / 10percent Pd/C / methanol; ethyl acetate / 3 h

3: 77 percent / 0.2 M LiOH / tetrahydrofuran; methanol; H₂O / 20 °C

4: 94 percent / K₂CO₃; Bu₄NI / dimethylformamide / 1 h / 20 °C

5: 87 percent / DCC; DMAP / CH₂Cl₂ / 0 - 20 °C

With 4-methyl-morpholine; dmap; lithium hydroxide; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; tetra-(n-butyl)ammonium iodide; potassium carbonate; dicyclohexyl-carbodiimide; 10percent Pd/C; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 1: Acylation / 2: Hydrogenolysis / 3: Hydrolysis / 4: Alkylation / 5: Acylation;

DOI:10.1021/jo000253a

upstream raw materials:

N_α-t-butoxycarbonyl-N_δ-xanthydryl-L-glutamine

L-lactyl-L-prolyl-N-methyl-D-leucine benzyl ester

methyl (2R)-4-methyl-2-(methylamino)pentanoate

L-lactyl-L-prolyl-N-methyl-D-leucine

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