methyl 2-tert-butoxycarbonylamino-3-carbobenzyloxy-4-phenyl-(2S,3R)-butanoate

Base Information

• Chemical Name: methyl 2-tert-butoxycarbonylamino-3-carbobenzyloxy-4-phenyl-(2S,3R)-butanoate
• CAS No.: 727740-00-3
• Molecular Formula: C₂₄H₂₉NO₆
• Molecular Weight: 427.497
• Mol file: 727740-00-3.mol

Synonyms:methyl 2-tert-butoxycarbonylamino-3-carbobenzyloxy-4-phenyl-(2S,3R)-butanoate

Chemical Property of methyl 2-tert-butoxycarbonylamino-3-carbobenzyloxy-4-phenyl-(2S,3R)-butanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-tert-butoxycarbonylamino-3-carbobenzyloxy-4-phenyl-(2S,3R)-butanoate

There total 1 articles about methyl 2-tert-butoxycarbonylamino-3-carbobenzyloxy-4-phenyl-(2S,3R)-butanoate 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: 62.0%

benzyl bromide (100-39-0) + 4-benzyl 1-methyl N-(tert-butoxycarbonyl)-L-aspartate (80963-12-8) → methyl 2-tert-butoxycarbonylamino-3-carbobenzyloxy-4-phenyl-(2S,3R)-butanoate (727740-00-3)

Guidance literature:

4-benzyl 1-methyl N-(tert-butoxycarbonyl)-L-aspartate; With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane; In tetrahydrofuran; at -42 ℃; for 0.5h;

benzyl bromide; In tetrahydrofuran; at -42 ℃; for 4h; Further stages.;

DOI:10.1016/j.tetlet.2004.03.146

Reference yield:

methyl 2-tert-butoxycarbonylamino-3-carbobenzyloxy-4-phenyl-(2S,3R)-butanoate (727740-00-3) → (2S,3R)-2-Benzyl-3-tert-butoxycarbonylamino-succinic acid 4-methyl ester

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 2h;

DOI:10.1016/j.tetlet.2004.03.146

Reference yield:

methyl 2-tert-butoxycarbonylamino-3-carbobenzyloxy-4-phenyl-(2S,3R)-butanoate (727740-00-3) → methyl 3-benzyl-2-tert-butoxycarbonylamino-4-hydroxy-(2S,3R)-butanoate (727740-02-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: H₂ / Pd/C / methanol / 2 h

2.1: BOP; DIPEA / tetrahydrofuran / 0.08 h

2.2: 1.2 g / NaHB₄ / tetrahydrofuran / 18.5 h / 0 - 20 °C

With hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1016/j.tetlet.2004.03.146

upstream raw materials:

benzyl bromide

4-benzyl 1-methyl N-(tert-butoxycarbonyl)-L-aspartate

Downstream raw materials:

methyl 3-benzyl-2-tert-butoxycarbonylamino-4-hydroxy-(2S,3R)-butanoate

methyl (3S,4R,5S,8R)-4-benzyl-3-tert-butoxycarbonylamino-1-aza-2-oxo-6-thiabicyclic [3.3.0]-octane-8-carboxylate