(S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid (S)-1-benzyloxycarbonyl-2-phenyl-ethyl ester

Base Information

• Chemical Name: (S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid (S)-1-benzyloxycarbonyl-2-phenyl-ethyl ester
• CAS No.: 155096-16-5
• Molecular Formula: C₂₆H₃₃NO₆
• Molecular Weight: 455.551
• Mol file: 155096-16-5.mol

Synonyms:(S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid (S)-1-benzyloxycarbonyl-2-phenyl-ethyl ester

Chemical Property of (S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid (S)-1-benzyloxycarbonyl-2-phenyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid (S)-1-benzyloxycarbonyl-2-phenyl-ethyl ester

There total 1 articles about (S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid (S)-1-benzyloxycarbonyl-2-phenyl-ethyl ester 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: 88.0%

t-Boc-L-valine (13734-41-3) + benzyl-(S)-(-)-2-hydroxy-3-phenylpropionate (7622-21-1) → (S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid (S)-1-benzyloxycarbonyl-2-phenyl-ethyl ester (155096-16-5)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/S0040-4039(00)61356-4

Reference yield:

(S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid (S)-1-benzyloxycarbonyl-2-phenyl-ethyl ester (155096-16-5) → (S)-2-Amino-3-methyl-butyric acid (S)-1-benzyloxycarbonyl-2-phenyl-ethyl ester

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(00)61356-4

Reference yield:

(S)-2-tert-Butoxycarbonylamino-3-methyl-butyric acid (S)-1-benzyloxycarbonyl-2-phenyl-ethyl ester (155096-16-5) → (S)-2-({(S)-2-[(2R,3R)-3-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-2-methyl-butyryloxy]-3-methyl-butyryl}-methyl-amino)-3-methyl-butyric acid (S)-1-carboxy-2-phenyl-ethyl ester

Guidance literature:

Multi-step reaction with 8 steps

1: CF₃COOH / CH₂Cl₂ / 0 °C

2: diethyl phosphorocyanidate, Et₃N / dimethylformamide / 0 - 20 °C

3: 75 percent / NaH / dimethylformamide / 0 °C

4: 98 percent / 12percent HF / H₂O; acetonitrile / Ambient temperature

5: 98 percent / DCC, DMAP, 10-camphorsulfonic acid / CH₂Cl₂ / 0 - 20 °C

6: CF₃COOH / CH₂Cl₂ / 0 °C

7: diethyl phosphorocyanidate, Et₃N / dimethylformamide / 0 - 20 °C

8: 91 percent / H₂ / 10percent Pd-C / methanol; H₂O; acetic acid / Ambient temperature

With dmap; diethyl cyanophosphonate; (1S)-10-camphorsulfonic acid; hydrogen fluoride; hydrogen; sodium hydride; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(00)61356-4

upstream raw materials:

t-Boc-L-valine

benzyl-(S)-(-)-2-hydroxy-3-phenylpropionate

Downstream raw materials:

(S)-2-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-butyrylamino]-3-methyl-butyric acid (S)-1-benzyloxycarbonyl-2-phenyl-ethyl ester

(S)-2-{[(S)-2-((2R,3R)-3-tert-Butoxycarbonylamino-2-methyl-butyryloxy)-3-methyl-butyryl]-methyl-amino}-3-methyl-butyric acid (S)-1-benzyloxycarbonyl-2-phenyl-ethyl ester

(S)-2-({(S)-2-[(2R,3R)-3-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-2-methyl-butyryloxy]-3-methyl-butyryl}-methyl-amino)-3-methyl-butyric acid (S)-1-benzyloxycarbonyl-2-phenyl-ethyl ester