D-Allylglycine

Base Information

• Chemical Name: D-Allylglycine
• CAS No.: 54594-06-8
• Molecular Formula: C5H9NO2
• Molecular Weight: 115.132
• Hs Code.: 29224999
• Nikkaji Number: J36.279D
• Wikidata: Q27459790
• ChEMBL ID: CHEMBL554311
• Mol file: 54594-06-8.mol

Synonyms:54594-06-8;D-Allylglycine;(R)-2-aminopent-4-enoic acid;H-D-Gly(allyl)-OH;(2R)-2-aminopent-4-enoic acid;(R)-2-Amino-4-pentenoic acid;(R)-2-amino-pent-4-enoic acid;(R)-Allylglycine;(+)-Allylglycine;D-alpha-Allyl-Gly;4-Pentenoic acid, 2-amino-, (2R)-;D-2-Amino-4-pentenoic acid;MFCD00063104;4-Pentenoic acid, 2-amino-, (R)-;(R)-2-Allylglycine;H-D-Algly-OH;H-D-Allylglycine;(2R)-2-amino-4-pentenoic acid;3-VINYL-D-ALANINE;SCHEMBL616036;(R)-2-amino-4-pentenoicacid;CHEMBL554311;WNNNWFKQCKFSDK-SCSAIBSYSA-N;4-Pentenoic acid,2-amino-,(2R)-;AC-877;(R)-(+)-2-Amino-4-pentenoic acid;AKOS016842837;AC-4462;CS-W013623;HY-W012907;AS-14703;D-|A inverted exclamation mark-Allyl-Gly;EN300-102381;A830257;Q27459790;(R)-Allylglycine (>98%, >99%ee) (H-D-AllylGly-OH);S-54594-06-8

Chemical Property of D-Allylglycine

Chemical Property:

• Appearance/Colour: off-white solid
• Melting Point: 239.3-241.2 °C
• Boiling Point: 231 °C at 760 mmHg
• PKA: 2.22±0.10(Predicted)
• Flash Point: 93.5 °C
• PSA: 49.33000
• Density: 1.098 g/cm³
• LogP: 0.23750
• Storage Temp.: 2-8°C
• Solubility.: Water (Slightly)
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 115.063328530
• Heavy Atom Count: 8
• Complexity: 101

Purity/Quality:

99% ^*data from raw suppliers

D-Allylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CCC(C(=O)O)N
• Isomeric SMILES: C=CC[C@H](C(=O)O)N
• Uses: D-Allylglycine is a new chiral glycine equivalent, it is used for the preparation of enantiomerically pure a-tertiary and a-quaternary a-amino acids. A Bacillus spore germination alanine analog.

Technology Process of D-Allylglycine

There total 65 articles about D-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: 99.0%

N-(allylglycinoyl)-(1R,2S)-bornane-10,2-sultam hydrochloride → D-allylglycine (54594-06-8)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 6h;

DOI:10.1021/ja043768i

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: 90.0%

→ D-allylglycine (54594-06-8)

Guidance literature:

With hydrogenchloride; In methanol; dichloromethane; water; at 60 ℃;

DOI:10.1016/j.tet.2004.06.087

upstream raw materials:

N-Acetyl-D-α-allylglycine

(R)-2-Amino-1-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-pent-4-en-1-one

α-allylglycine amide

(R)-2-allylglycine hydrochloride

Downstream raw materials:

D-2-aminopent-4-enoic acid benzyl ester toluene-4-sulphonate salt

(R)-2-allylglycine methyl ester

N-Boc-D-Leu

N-(tert-butoxycarbonyl)-D-allylglycine

Refernces

• 1、 Workman, James A.,Garrido, Neil P.,Sancon, Julien,Roberts, Edward,Wessel, Hans Peter,Sweeney. "Asymmetric [2,3]-rearrangement of glycine-derived allyl ammonium ylids". . p. 1066 - 1067. Retrieved 2005.
• 2、 Sugiyama, Shigeo,Imai, Saori,Ishii, Keitaro. "Diastereoselective amidoallylation of glyoxylic acid with chiral tert-butanesulfinamide and allylboronic acid pinacol esters: Efficient synthesis of optically active γ,δ-unsaturated α-amino acids This work is dedicated to Dr. Masanori Sakamoto, Professor Emeritus of Meiji Pharmaceutical University, on the occasion of his 77th birthday (KIJU)". . p. 1069 - 1074. Retrieved 2013/10/08.
• 3、 Baxter, Scott,Royer, Sylvain,Grogan, Gideon,Brown, Fraser,Holt-Tiffin, Karen E.,Taylor, Ian N.,Fotheringham, Ian G.,Campopiano, Dominic J.. "An improved racemase/acylase biotransformation for the preparation of enantiomerically pure amino acids". supporting information. p. 19310 - 19313. Retrieved 2013/02/23.