(2S,3S)-1-tert-butyl 4-methyl N-(tert-butoxycarbonyl)-3-benzylaspartate

Base Information

• Chemical Name: (2S,3S)-1-tert-butyl 4-methyl N-(tert-butoxycarbonyl)-3-benzylaspartate
• CAS No.: 128576-63-6
• Molecular Formula: C₂₁H₃₁NO₆
• Molecular Weight: 393.48
• Mol file: 128576-63-6.mol

Synonyms:

Chemical Property of (2S,3S)-1-tert-butyl 4-methyl N-(tert-butoxycarbonyl)-3-benzylaspartate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-1-tert-butyl 4-methyl N-(tert-butoxycarbonyl)-3-benzylaspartate

There total 10 articles about (2S,3S)-1-tert-butyl 4-methyl N-(tert-butoxycarbonyl)-3-benzylaspartate 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:

benzyl bromide (100-39-0) → (2S,3S)-1-tert-butyl 4-methyl N-(tert-butoxycarbonyl)-3-benzylaspartate (128576-63-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) KHMDS / 1) THF, toluene, -20 deg C; 2) -20 deg C, 2 h; 3) ethanol

2: 90 percent / 20percent Pd(OH)2/C, H₂ / acetic acid / 24 h / 760 Torr / Ambient temperature

3: acetonitrile / 4 h / Ambient temperature

With palladium dihydroxide; hydrogen; potassium hexamethylsilazane; In acetic acid; acetonitrile;

DOI:10.1021/jo00304a011

Reference yield:

1-tert-butyl 4-methyl (2S)-2-(benzylamino)butanedioate (128576-60-3) → (2S,3S)-1-tert-butyl 4-methyl N-(tert-butoxycarbonyl)-3-benzylaspartate (128576-63-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / Pb(NO₃)2, K₃PO₄ / acetonitrile / 16 h / Ambient temperature

2: 1) KHMDS / 1) THF, toluene, -20 deg C; 2) -20 deg C, 2 h; 3) ethanol

3: 90 percent / 20percent Pd(OH)2/C, H₂ / acetic acid / 24 h / 760 Torr / Ambient temperature

4: acetonitrile / 4 h / Ambient temperature

With palladium dihydroxide; potassium phosphate; lead(II) nitrate; hydrogen; potassium hexamethylsilazane; In acetic acid; acetonitrile;

DOI:10.1021/jo00304a011

Reference yield:

(2S)-4-benzyl 1-tert-butyl N-benzylaspartate (128576-65-8) → (2S,3S)-1-tert-butyl 4-methyl N-(tert-butoxycarbonyl)-3-benzylaspartate (128576-63-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / Pb(NO₃)2, K₃PO₄ / acetonitrile / 17 h / Ambient temperature

2: 1) KHMDS / 1) THF, toluene, -20 deg C; 2) THF, -20 deg C, 2 h

3: 78 percent / 5percent Pd/BaSO₄, H₂ / ethyl acetate / 18 h / 760 Torr / Ambient temperature

5: 90 percent / 20percent Pd(OH)2/C, H₂ / acetic acid / 24 h / 760 Torr / Ambient temperature

6: acetonitrile / 4 h / Ambient temperature

With palladium dihydroxide; potassium phosphate; Pd-BaSO₄; lead(II) nitrate; hydrogen; potassium hexamethylsilazane; In acetic acid; ethyl acetate; acetonitrile;

DOI:10.1021/jo00304a011

upstream raw materials:

di-tert-butyl dicarbonate

(2S,3S)-2-Amino-3-benzyl-succinic acid 1-tert-butyl ester 4-methyl ester

benzyl bromide

1-tert-butyl 4-methyl (2S)-2-(benzylamino)butanedioate

Downstream raw materials:

(2S,3S) and (2S,3R)-1-tert-butyl N-(tert-butoxycarbonyl)-3-benzylaspartate