tert-butyl (S)-1-azido-3-(1-trityl-1H-imidazol-4-yl)propan-2-ylcarbamate

Base Information

• Chemical Name: tert-butyl (S)-1-azido-3-(1-trityl-1H-imidazol-4-yl)propan-2-ylcarbamate
• CAS No.: 1376948-13-8
• Molecular Formula: C₃₀H₃₂N₆O₂
• Molecular Weight: 508.623

Synonyms:tert-butyl (S)-1-azido-3-(1-trityl-1H-imidazol-4-yl)propan-2-ylcarbamate

Chemical Property of tert-butyl (S)-1-azido-3-(1-trityl-1H-imidazol-4-yl)propan-2-ylcarbamate

Chemical Property:

Purity/Quality:

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Technology Process of tert-butyl (S)-1-azido-3-(1-trityl-1H-imidazol-4-yl)propan-2-ylcarbamate

There total 2 articles about tert-butyl (S)-1-azido-3-(1-trityl-1H-imidazol-4-yl)propan-2-ylcarbamate 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: 76.0%

di-tert-butyl dicarbonate (24424-99-5) + (S)-1-azido-N-trityl-3-(1-trityl-1H-imidazol-4-yl)propan-2-amine (1376948-10-5) → tert-butyl (S)-1-azido-3-(1-trityl-1H-imidazol-4-yl)propan-2-ylcarbamate (1376948-13-8)

Guidance literature:

(S)-1-azido-N-trityl-3-(1-trityl-1H-imidazol-4-yl)propan-2-amine; With trifluoroacetic acid; In methanol; 1,2-dichloro-ethane; at 0 - 10 ℃; for 0.166667h;

di-tert-butyl dicarbonate; With triethylamine; In methanol; 1,2-dichloro-ethane; at 20 ℃; for 0.333333h;

DOI:10.1016/j.tet.2011.11.066

Reference yield:

2-(S)-(triphenylmethylamino)-3-<1-(triphenylmethyl)imidazol-4(5)-yl>propanol ditrityl-L-histidinol (223910-41-6) → tert-butyl (S)-1-azido-3-(1-trityl-1H-imidazol-4-yl)propan-2-ylcarbamate (1376948-13-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 5 h / 65 °C

1.2: 12 h / 65 °C

2.1: trifluoroacetic acid / methanol; 1,2-dichloro-ethane / 0.17 h / 0 - 10 °C

2.2: 0.33 h / 20 °C

With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2011.11.066

Reference yield: 100.0%

tert-butyl (S)-1-azido-3-(1-trityl-1H-imidazol-4-yl)propan-2-ylcarbamate (1376948-13-8) → tert-butyl (S)-1-amino-3-(1-trityl-1H-imidazol-4-yl)propan-2-ylcarbamate (1376947-77-1)

Guidance literature:

With 5% Pd-BaSO4; hydrogen; In ethyl acetate; at 20 ℃; for 20h;

DOI:10.1016/j.tet.2011.11.066

upstream raw materials:

di-tert-butyl dicarbonate

(S)-1-azido-N-trityl-3-(1-trityl-1H-imidazol-4-yl)propan-2-amine

2-(S)-(triphenylmethylamino)-3-<1-(triphenylmethyl)imidazol-4(5)-yl>propanol ditrityl-L-histidinol

Downstream raw materials:

C₃₅H₃₇N₅O₆

tert-butyl (S)-1-amino-3-(1-trityl-1H-imidazol-4-yl)propan-2-ylcarbamate

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