L-Allylglycine

Base Information

• Chemical Name: L-Allylglycine
• CAS No.: 16338-48-0
• Molecular Formula: C5H9NO2
• Molecular Weight: 115.132
• Hs Code.: 29224999
• Mol file: 16338-48-0.mol

Synonyms:(2S)-2-aminopent-4-enoic acid;4-Pentenoic acid, 2-amino-, (S)-;(-)-Allylglycine;L-Allylglycine;(S)-2-Amino-4-pentenoic acid;L-alpha-Allyl-Gly;

Chemical Property of L-Allylglycine

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Vapor Pressure: 0.0226mmHg at 25°C
• Melting Point: 253-255 °C
• Refractive Index: 1.484
• Boiling Point: 231 °C at 760 mmHg
• PKA: 2.22±0.10(Predicted)
• Flash Point: 93.5 °C
• PSA: 63.32000
• Density: 1.098 g/cm³
• LogP: 0.67470
• Storage Temp.: 2-8°C
• Solubility.: H2O: 100 mg/mL
• Water Solubility.: soluble

Purity/Quality:

98%,99%, ^*data from raw suppliers

L-Allylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: L-Allylglycine is a glutamic acid decarboxylase inhibitor.

Technology Process of L-Allylglycine

There total 28 articles about L-Allylglycine 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: 90.0%

(3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(2'-propenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (100516-55-0) → D-allylglycine (54594-06-8) + L-allylglycine (16338-48-0)

Guidance literature:

With ammonia; lithium; In tetrahydrofuran; ethanol; for 1h; Yields of byproduct given;

DOI:10.1021/ja00213a031

Reference yield:

allyl bromide (106-95-6) + glycine (56-40-6,18875-39-3,25718-94-9) → D-allylglycine (54594-06-8) + L-allylglycine (16338-48-0)

Guidance literature:

glycine; With pyridine-2-carboxylic acid(2-benzoyl-phenyl)-amide; sodium methylate; nickel(II) nitrate; In methanol; for 0.333333h; Heating;

allyl bromide; With sodium hydroxide; (R)-2-amino-2'-hydroxy-1,1'-binaphthyl; In dichloromethane; at 20 ℃; for 0.5h;

With hydrogenchloride; In methanol; water; Heating;

DOI:10.1002/1521-3773(20010518)40:10<1948::AID-ANIE1948>3.0.CO;2-O

Reference yield:

allyl iodid (556-56-9) + glycine (56-40-6,18875-39-3,25718-94-9) → D-allylglycine (54594-06-8) + L-allylglycine (16338-48-0)

Guidance literature:

glycine; With pyridine-2-carboxylic acid(2-benzoyl-phenyl)-amide; sodium methylate; nickel(II) nitrate; In methanol; for 0.333333h; Heating;

allyl iodid; With sodium hydroxide; (R)-2-amino-2'-hydroxy-1,1'-binaphthyl; In dichloromethane; at 20 ℃; for 0.0666667h;

With hydrogenchloride; In methanol; water; Heating;

DOI:10.1002/1521-3773(20010518)40:10<1948::AID-ANIE1948>3.0.CO;2-O

upstream raw materials:

α-allylglycine amide

benzaldehyde

2-Amino-N-methoxy-4-pentenamide

(3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(2'-propenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

Downstream raw materials:

(S)-2-(benzyloxycarbonylamino)pent-4-enoic acid

(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid

methyl (S)-allylglycinate

(2S)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pent-4-enoic acid

Refernces

• 1、 -. "METHOD FOR SYNTHESIZING OPTICALLY ACTIVE a-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL] ACETAMIDE COMPOUND AND AMINO ACID". Paragraph 0339-0341. . Retrieved 2016/05/10.
• 2、 Noisier, Anais F. M.,Harris, Craig S.,Brimble, Margaret A.. "Novel preparation of chiral α-amino acids using the Mitsunobu-Tsunoda reaction". supporting information. p. 7744 - 7746. Retrieved 2013/09/02.