N-TERT-BUTOXYCARBONYL-AZIDO-D-ALANINE

Base Information

• Chemical Name: N-TERT-BUTOXYCARBONYL-AZIDO-D-ALANINE
• CAS No.: 225780-77-8
• Molecular Formula: C8H14N4O4
• Molecular Weight: 230.224
• Hs Code.: 9999999999
• Mol file: 225780-77-8.mol

Synonyms:Boc-D-Dap(N3) CHA salt;N-TERT-BUTOXYCARBONYL-AZIDO-D-ALANINE;Boc-D-Aza-OH*CHA;3-Azido-N-[(1,1-dimethylethoxy)carbonyl]-D-alanine;3-Azido-N-Boc-D-alanine

Chemical Property of N-TERT-BUTOXYCARBONYL-AZIDO-D-ALANINE

Chemical Property:

• PSA: 125.38000
• LogP: 1.11826

Purity/Quality:

98% ^*data from raw suppliers

Boc-D-Aza-OH*CHA ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-TERT-BUTOXYCARBONYL-AZIDO-D-ALANINE

There total 3 articles about N-TERT-BUTOXYCARBONYL-AZIDO-D-ALANINE 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: 85.0%

N-(tert-butyloxycarbonyl)-D-serine β-lactone (98541-64-1,132340-68-2,126330-77-6) → 2-(R)-(tert-butoxycarbonyl)-amino-3-azidopropionic acid (225780-77-8,108283-49-4)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; 1.) 0 deg C, 45 min, 2.) room temperature, 1 h;

DOI:10.1016/S0968-0896(98)00254-5

Reference yield:

methyl (R)-3-azido-2-[(tert-butyloxycarbonyl)amino]propionate (301671-17-0) → 2-(R)-(tert-butoxycarbonyl)-amino-3-azidopropionic acid (225780-77-8,108283-49-4)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; Inert atmosphere;

DOI:10.1002/chem.201200457

Reference yield:

2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester (95715-85-8) → 2-(R)-(tert-butoxycarbonyl)-amino-3-azidopropionic acid (225780-77-8,108283-49-4)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate; C₇H₈*HN₃ / tetrahydrofuran / 7 h / -20 °C

2: lithium hydroxide / tetrahydrofuran; water / 1 h / 0 °C

With di-isopropyl azodicarboxylate; C₇H₈*HN₃; triphenylphosphine; lithium hydroxide; In tetrahydrofuran; water;

DOI:10.1021/jm301058f

upstream raw materials:

N-(tert-butyloxycarbonyl)-D-serine β-lactone

methyl (R)-3-azido-2-[(tert-butyloxycarbonyl)amino]propionate

2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester

Downstream raw materials:

(R)-2-tert-butoxycarbonyl-3-aminopropionic acid

C₂₁H₂₉N₅O₇

(S)-dimethyl-2-((R)-3-azido-2-(tert-butoxycarbonylamino)-N-(4-((4-methoxy-2,3,6-trimethylphenylsulfonamido)methyl)benzyl)propanamido)succinate

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