D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4S)-

Base Information

• Chemical Name: D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4S)-
• CAS No.: 400769-77-9
• Molecular Formula: C14H16N2O5
• Molecular Weight: 292.291
• DSSTox Substance ID: DTXSID80431111
• Nikkaji Number: J2.180.702H
• Wikidata: Q82244915
• Mol file: 400769-77-9.mol

Synonyms:400769-77-9;(2R,4S)-Monatin;(2S,4R)-2-((1H-Indol-3-yl)methyl)-4-amino-2-hydroxypentanedioic acid;D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4S)-;SCHEMBL6003061;DTXSID80431111;RMLYXMMBIZLGAQ-YGRLFVJLSA-N;(2R, 4S)-4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid;(2R,4S)-4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid;(2R, 4S)-4-hydroxy-4-(3-indolylmethyl) -2-aminoglutaric acid;(2S,4R)-4-amino-2-hydroxy-2-[(1H-indol-3-yl)methyl]pentanedioic acid

Chemical Property of D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4S)-

Chemical Property:

• XLogP3: -2.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 292.10592162
• Heavy Atom Count: 21
• Complexity: 416

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CC(CC(C(=O)O)N)(C(=O)O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(=CN2)C[C@](C[C@H](C(=O)O)N)(C(=O)O)O

Technology Process of D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4S)-

There total 4 articles about D-Glutamic acid, 4-hydroxy-4-(1H-indol-3-ylmethyl)-, (4S)- 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:

isoxazoline diethyl ester → (2R,4R)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid (400769-81-5) + (2S,4R) 4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid (400769-77-9) + (2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid (146142-94-1) + (2S,4R)-monatin (400769-79-1)

Guidance literature:

isoxazoline diethyl ester; With potassium hydroxide; water; sponge nickel catalyst A-7063; In ethanol; for 0.0833333h; Sealed reactor;

With hydrogen; In ethanol; water; at 20 ℃; for 1.5h; under 3750.38 Torr; Product distribution / selectivity; Sealed reactor;

Reference yield:

4-hydroxy-4-(3-indolylmethyl)-2-hydroxyiminoglutaric acid di-ammonium salt → (2R,4R)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid (400769-81-5) + (2S,4R) 4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid (400769-77-9) + (2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid (146142-94-1) + (2S,4R)-monatin (400769-79-1)

Guidance literature:

With ammonia; hydrogen; 5% rhodium-on-charcoal; In water; at 25 ℃; for 24h; under 7500.75 Torr; Product distribution / selectivity;

Reference yield:

(2R,4S)-4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)-pentanedioic acid ammonium salt + (2S,4R)-4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)-pentanedioic acid ammonium salt → (2R,4R)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid (400769-81-5) + (2S,4R) 4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid (400769-77-9) + (2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid (146142-94-1)

Guidance literature:

With methanol; salicylaldehyde; acetic acid; at 80 ℃; for 16h; Product distribution / selectivity;

upstream raw materials:

4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)-pentanedioic acid

Downstream raw materials:

(2R,4R)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid

(2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid