N^α,N^β-bis((tert-butyloxy)carbonyl)-N^β-<(4-amino-6-(amido-N^im-(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)-5-methylpyrimidin-2-yl)methylene>-(S)-β-aminoalanine amide

Base Information

• Chemical Name: N^α,N^β-bis((tert-butyloxy)carbonyl)-N^β-<(4-amino-6-(amido-N^im-(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)-5-methylpyrimidin-2-yl)methylene>-(S)-β-aminoalanine amide
• CAS No.: 142582-35-2
• Molecular Formula: C₄₅H₅₃N₉O₉
• Molecular Weight: 863.971

Synonyms:N^α,N^β-bis((tert-butyloxy)carbonyl)-N^β-<(4-amino-6-(amido-N^im-(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)-5-methylpyrimidin-2-yl)methylene>-(S)-β-aminoalanine amide

Chemical Property of N^α,N^β-bis((tert-butyloxy)carbonyl)-N^β-<(4-amino-6-(amido-N^im-(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)-5-methylpyrimidin-2-yl)methylene>-(S)-β-aminoalanine amide

Chemical Property:

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Technology Process of N^α,N^β-bis((tert-butyloxy)carbonyl)-N^β-<(4-amino-6-(amido-N^im-(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)-5-methylpyrimidin-2-yl)methylene>-(S)-β-aminoalanine amide

There total 10 articles about N^α,N^β-bis((tert-butyloxy)carbonyl)-N^β-<(4-amino-6-(amido-N^im-(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)-5-methylpyrimidin-2-yl)methylene>-(S)-β-aminoalanine amide 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: 92.0%

Nα,Nβ-bis((tert-butyloxy)carbonyl)-Nβ-<(4-amino-6-(amido-Nim-(triphenylmethyl)-erythro-β-hydroxy-L-histidyl methyl ester)-5-methylpyrimidin-2-yl)methylene>-(S)-β-aminoalanine amide (142582-34-1) → Nα,Nβ-bis((tert-butyloxy)carbonyl)-Nβ-<(4-amino-6-(amido-Nim-(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)-5-methylpyrimidin-2-yl)methylene>-(S)-β-aminoalanine amide (142582-35-2)

Guidance literature:

With lithium hydroxide; water; In tetrahydrofuran; methanol; at 25 ℃; for 3h;

DOI:10.1021/jo00042a004

Reference yield:

Nα,Nβ-bis(tert-butoxycarbonyl)-Nβ-<(4-amino-6-carboxy-5-methylpyrimidin-2-yl)methyl>-(S)-β-aminoalanineamide (129812-61-9) → Nα,Nβ-bis((tert-butyloxy)carbonyl)-Nβ-<(4-amino-6-(amido-Nim-(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)-5-methylpyrimidin-2-yl)methylene>-(S)-β-aminoalanine amide (142582-35-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / HOBt, EDCI / tetrahydrofuran; dimethylformamide / 72 h / 25 °C

2: 92 percent / 1 N aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C

With lithium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

Reference yield:

erythro-N?-Triphenylmethyl-β-hydroxy-L-histidinmethylester (142582-33-0) → Nα,Nβ-bis((tert-butyloxy)carbonyl)-Nβ-<(4-amino-6-(amido-Nim-(triphenylmethyl)-erythro-β-hydroxy-L-histidyl)-5-methylpyrimidin-2-yl)methylene>-(S)-β-aminoalanine amide (142582-35-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / HOBt, EDCI / tetrahydrofuran; dimethylformamide / 72 h / 25 °C

2: 92 percent / 1 N aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C

With lithium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

upstream raw materials:

N^α,N^β-bis((tert-butyloxy)carbonyl)-N^β-<(4-amino-6-(amido-N^im-(triphenylmethyl)-erythro-β-hydroxy-L-histidyl methyl ester)-5-methylpyrimidin-2-yl)methylene>-(S)-β-aminoalanine amide

N^α,N^β-bis(tert-butoxycarbonyl)-N^β-<(4-amino-6-carboxy-5-methylpyrimidin-2-yl)methyl>-(S)-β-aminoalanineamide

erythro-N^?-Triphenylmethyl-β-hydroxy-L-histidinmethylester

di-tert-butyl dicarbonate

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