(2S,3S)-3-benzylglutamic acid

Base Information

• Chemical Name: (2S,3S)-3-benzylglutamic acid
• CAS No.: 126643-08-1
• Molecular Formula: C₁₂H₁₅NO₄
• Molecular Weight: 237.255
• Mol file: 126643-08-1.mol

Synonyms:

Chemical Property of (2S,3S)-3-benzylglutamic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-benzylglutamic acid

There total 8 articles about (2S,3S)-3-benzylglutamic acid 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:

(2S,3S)-3-Benzyl-2-tert-butoxycarbonylamino-pentanedioic acid → (2S,3S)-3-benzylglutamic acid (126643-08-1)

Guidance literature:

With trifluoroacetic acid; Yield given;

DOI:10.1016/S0040-4039(01)80659-6

Reference yield:

(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate (81658-27-7) → (2S,3S)-3-benzylglutamic acid (126643-08-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) BuLi, TMEDA / 1.) THF, hexane, -78 deg C, 15 min, 2.) THF, hexane, -78 deg C, 1 h

2: 98 percent / Raney Ni (W-2) / acetone; H₂O / 12 h / 56 °C

3: 1M aq. NaOH / tetrahydrofuran / 12 h / 25 °C

4: methanol; diethyl ether

5: 77 percent / 10percent aq. HF / acetonitrile / 0.5 h / 25 °C

6: 1M aq. NaOH, KMnO₄ / 12 h / 25 °C

7: TFA / 0.25 h / 25 °C

With sodium hydroxide; potassium permanganate; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; Raney Ni (W-2); hydrogen fluoride; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; water; acetone; acetonitrile;

DOI:10.1016/0040-4020(95)01058-0

Reference yield:

(3S,4S)-3-Benzyl-4-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid → (2S,3S)-3-benzylglutamic acid (126643-08-1)

Guidance literature:

Multi-step reaction with 4 steps

1: methanol; diethyl ether

2: 77 percent / 10percent aq. HF / acetonitrile / 0.5 h / 25 °C

3: 1M aq. NaOH, KMnO₄ / 12 h / 25 °C

4: TFA / 0.25 h / 25 °C

With sodium hydroxide; potassium permanganate; hydrogen fluoride; trifluoroacetic acid; In methanol; diethyl ether; acetonitrile;

DOI:10.1016/0040-4020(95)01058-0

upstream raw materials:

Benzyl phenyl sulfide

(S)-tert-butyl 2-(((tert-butyldimethylsilyl)oxy)methyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate

(2S,3S)-3-benzyl-1-<(1,1-dimethylethoxy)carbonyl>-2-<<(1,1-dimethylethyl)dimethylsilyloxy>methyl>-5-pyrrolidone

methyl (3S,4S)-3-benzyl-5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-<<(1,1-dimethylethoxy)carbonyl>amino>pentanoate

Refernces

• 1、 Yanagida, Miwa,Hashimoto, Kimiko,Ishida, Michiko,Shinozaki, Haruhiko,Shirahama, Haruhisa. "SYNTHESIS OF ACYCLIC ANALOGUES OF KAINOIDS AND NEUROEXCITATORY ACTIVITY". . p. 3799 - 3802. Retrieved 2007/10/02.