N-(tert-butoxycarbonyl)-3-azido-L-alanine amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

Base Information

• Chemical Name: N-(tert-butoxycarbonyl)-3-azido-L-alanine amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane
• CAS No.: 146879-03-0
• Molecular Formula: C₂₂H₄₁N₅O₅
• Molecular Weight: 455.598
• Mol file: 146879-03-0.mol

Synonyms:N-(tert-butoxycarbonyl)-3-azido-L-alanine amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

Chemical Property of N-(tert-butoxycarbonyl)-3-azido-L-alanine amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(tert-butoxycarbonyl)-3-azido-L-alanine amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

There total 4 articles about N-(tert-butoxycarbonyl)-3-azido-L-alanine amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane 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: 59.0%

(2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane (122621-77-6) + (S)-3-azido-2-((tert-butoxycarbonyl)amino)propanoic acid (122225-54-1,108283-49-4) → N-(tert-butoxycarbonyl)-3-azido-L-alanine amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane (146879-03-0)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; 1.) -23 deg C, 2 h, 2.) RT, 15 h;

DOI:10.1021/jm00056a005

Reference yield:

N-tert-butyloxycarbonyl-L-serine methyl ester (2766-43-0) → N-(tert-butoxycarbonyl)-3-azido-L-alanine amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane (146879-03-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / Ph₃P, diethyl azodicarboxylate, HN₃ / benzene; tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) RT, 16 h

2: 76 percent / aq. LiOH / dioxane / 1 h / 0 °C

3: 59 percent / 1-hydroxybenzotriazole, N-methylmorpholine, 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride (EDC) / dimethylformamide / 1.) -23 deg C, 2 h, 2.) RT, 15 h

With 4-methyl-morpholine; lithium hydroxide; tris-(2-chloro-ethyl)-amine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm00056a005

Reference yield:

(2S,3R,4S)-2-[(tert-butyloxycarbonyl)amino]-1-cyclohexyl-3,4-dihydroxy-6-methylheptane (104882-10-2) → N-(tert-butoxycarbonyl)-3-azido-L-alanine amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane (146879-03-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / 4 M HCl / dioxane / 1 h / Ambient temperature

2: 59 percent / 1-hydroxybenzotriazole, N-methylmorpholine, 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride (EDC) / dimethylformamide / 1.) -23 deg C, 2 h, 2.) RT, 15 h

With 4-methyl-morpholine; hydrogenchloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/jm00056a005

upstream raw materials:

(2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

(S)-3-azido-2-((tert-butoxycarbonyl)amino)propanoic acid

N-tert-butyloxycarbonyl-L-serine methyl ester

(2S,3R,4S)-2-[(tert-butyloxycarbonyl)amino]-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

Downstream raw materials:

H-3-azido-L-alanine amide of (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane

(R)-N-[(S)-2-Azido-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-ethyl]-2-benzyl-4-morpholin-4-yl-4-oxo-butyramide