methyl (2S,3R)-2-((tert-butyloxycarbonyl)amino)-3-hydroxy-3-phenylpropionate

Base Information

• Chemical Name: methyl (2S,3R)-2-((tert-butyloxycarbonyl)amino)-3-hydroxy-3-phenylpropionate
• CAS No.: 136620-75-2
• Molecular Formula: C₁₅H₂₁NO₅
• Molecular Weight: 295.335

Synonyms:methyl (2S,3R)-2-((tert-butyloxycarbonyl)amino)-3-hydroxy-3-phenylpropionate

Chemical Property of methyl (2S,3R)-2-((tert-butyloxycarbonyl)amino)-3-hydroxy-3-phenylpropionate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

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Technology Process of methyl (2S,3R)-2-((tert-butyloxycarbonyl)amino)-3-hydroxy-3-phenylpropionate

There total 75 articles about methyl (2S,3R)-2-((tert-butyloxycarbonyl)amino)-3-hydroxy-3-phenylpropionate 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: 95.0%

methyl 2-((tert-butoxycarbonyl)amino)-3-oxo-3-phenylpropanoate (147744-97-6) → erythro-N-(tert-butoxycarbonyl)-β-hydroxy-L-phenylalanine methyl ester (17193-36-1,17324-91-3,136620-75-2,136620-82-1)

Guidance literature:

With dichloro(benzene)ruthenium(II) dimer; triethylammonium formate; (1S,2S)-2-(benzylamino)-1,2-diphenylethanol; In isopropyl alcohol; at 20 ℃; for 168h; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/ol102323k

Reference yield: 91.0%

di-tert-butyl dicarbonate (24424-99-5) + (2S,3R)-methyl 2-amino-3-hydroxy-3-phenylpropanoate hydrochloride salt → methyl (2S,3R)-2-((tert-butyloxycarbonyl)amino)-3-hydroxy-3-phenylpropionate (136620-75-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 3.5h;

DOI:10.1007/s00726-009-0466-x

Reference yield: 91.0%

4-methyl 3-(1,1-dimethylethyl) cis-2-oxo-5-phenyl-3,4-oxazolidinedicarboxylate → (±)-(2R,3R)-2-tert-butoxycarbonylamino-3-hydroxy-3-phenylpropionic acid methyl ester (17193-36-1,17324-91-3,136620-75-2,136620-82-1)

Guidance literature:

With caesium carbonate; In methanol; at 0 ℃; for 3h;

DOI:10.1248/cpb.53.355

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

methyl (2RS,3SR)-2-amino-3-hydroxy-3-phenylpropanoate hydrochloride

di-tert-butyl dicarbonate

(+/-)-methyl (βR)-β-hydroxy-1-phenylalaninate

Downstream raw materials:

Boc-β-OHPhe-OH

H-β-OH-Phe-OMe

methyl (Z)-N-Boc-α,β-didehydrophenylalaninate

(2S*,3R*)-2-tert-butoxycarbonylamino-3-hydroxy-3-phenyl-propionic acid methyl ester

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