(S)-2-(((Benzyloxy)carbonyl)amino)hexanedioic acid

Base Information

• Chemical Name: (S)-2-(((Benzyloxy)carbonyl)amino)hexanedioic acid
• CAS No.: 24325-14-2
• Molecular Formula: C14H17 N O6
• Molecular Weight: 295.292
• DSSTox Substance ID: DTXSID40427176
• Nikkaji Number: J2.210.922G
• Wikidata: Q72441870
• Mol file: 24325-14-2.mol

Synonyms:24325-14-2;(S)-2-(((Benzyloxy)carbonyl)amino)hexanedioic acid;Cbz-Aad-OH;Z-AAD-OH;(2S)-2-(phenylmethoxycarbonylamino)hexanedioic acid;Cbz-(S)-2-aminoadipic acid;(S)-2-(((Benzyloxy)carbonyl)amino)hexanedioicacid;SCHEMBL5711264;DTXSID40427176;SFOMJKAHGVQMPU-NSHDSACASA-N;(S)-2-(Z-Amino)-hexanedioic acid;MFCD00237377;AKOS016003129;(2S)-2-benzyloxycarbonylaminoadipic acid;(2S)-2-(Benzyloxycarbonylamino)adipic acid;CS-0323898;(S)-2-(benzyloxycarbonylamino)hexanedioic acid;C78089;Z-L--aminoadipic acid;(S)-2-(Z-amino)-hexanedioic acid;Z-Homoglu-OH

Chemical Property of (S)-2-(((Benzyloxy)carbonyl)amino)hexanedioic acid

Chemical Property:

• Melting Point: 163℃
• Boiling Point: 551.9±50.0 °C(Predicted)
• PKA: 3.91±0.21(Predicted)
• PSA: 112.93000
• Density: 1.322±0.06 g/cm3(Predicted)
• LogP: 2.01180
• Storage Temp.: Store at RT.
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 295.10558726
• Heavy Atom Count: 21
• Complexity: 365

Purity/Quality:

98.5% ^*data from raw suppliers

Z-L-alpha-aminoadipic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CCCC(=O)O)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@@H](CCCC(=O)O)C(=O)O

Technology Process of (S)-2-(((Benzyloxy)carbonyl)amino)hexanedioic acid

There total 13 articles about (S)-2-(((Benzyloxy)carbonyl)amino)hexanedioic 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: 99.0%

(S)-3-(benzyloxycarbonyl)-4-(4-diazo-3-oxobutyl)-5-oxazolidinone (58456-27-2) → (2S)-2-[(phenylmethoxy)carbonyl]aminoadipic acid (24325-14-2)

Guidance literature:

With silver benzoate; triethylamine; In tetrahydrofuran; water; for 0.5h; Ambient temperature;

Reference yield: 92.0%

L-homoglutamic acid (1118-90-7) → (2S)-2-[(phenylmethoxy)carbonyl]aminoadipic acid (24325-14-2)

Guidance literature:

DOI:10.1016/S0040-4020(01)96782-1

Reference yield: 86.3%

L-homoglutamic acid (1118-90-7) + benzyl chloroformate (501-53-1,94274-21-2) → (2S)-2-[(phenylmethoxy)carbonyl]aminoadipic acid (24325-14-2)

Guidance literature:

With sodium hydroxide; In water; Cooling with ice;

DOI:10.1039/b818206j

upstream raw materials:

L-homoglutamic acid

benzyl chloroformate

(S)-2-(((benzyloxy)carbonyl)amino)-6-hydroxyhexanoic acid

(S)-3-(benzyloxycarbonyl)-4-(4-diazo-3-oxobutyl)-5-oxazolidinone

Downstream raw materials:

p-nitrobenzyl N-benzyloxycarbonyl-L-α-aminoadipate

N',N''-didodecyl-L-2-(Nα-benzyloxycarbonylamino)adipamide

N-benzyloxycarbonyl-α-benzylester-δ-L-α-aminoadipic acid

L-4-(3-(benzyloxycarbonyl)-5-oxo-1,3-oxazolidin-4-yl)butanoic acid

Refernces

• 1、 Hachisako, Hiroshi,Ryu, Naoya,Murakami, Ryoichi. "Molecular structural requirements, dye specificity, and application of anionic peptide amphiphiles that induce intense fluorescence in cationic dyes". supporting information; experimental part. p. 2327 - 2337. Retrieved 2009/09/26.
• 2、 -. "THIAZOLIDINE DERIVATIVES". . . Retrieved 2008/06/13.