(S)-2-((tert-Butoxycarbonyl)amino)hexanedioic acid

Base Information

• Chemical Name: (S)-2-((tert-Butoxycarbonyl)amino)hexanedioic acid
• CAS No.: 77302-72-8
• Molecular Formula: C11H19 N O6
• Molecular Weight: 261.27
• DSSTox Substance ID: DTXSID70457683
• Nikkaji Number: J2.381.303C
• Wikidata: Q72510209
• Mol file: 77302-72-8.mol

Synonyms:77302-72-8;(S)-2-((tert-Butoxycarbonyl)amino)hexanedioic acid;BOC-L-2-AMINOADIPIC ACID;Boc-Aad-OH;Boc-(S)-2-aminoadipic acid;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanedioic acid;Hexanedioic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, (S)-;(2S)-2-[(tert-butoxycarbonyl)amino]hexanedioic acid;SCHEMBL3431559;DTXSID70457683;MFCD00063354;AKOS016008625;Boc-Aad-OH, >=98.0% (TLC);AS-68372;(S)-2-(tert-Butoxycarbonylamino)adipic acid;CS-0154529;C78459;A865306;(2S)-2-{[(tert-butoxy)carbonyl]amino}hexanedioic acid

Chemical Property of (S)-2-((tert-Butoxycarbonyl)amino)hexanedioic acid

Chemical Property:

• Vapor Pressure: 8.04E-10mmHg at 25°C
• Melting Point: 121-122℃
• Refractive Index: 1.491
• Boiling Point: 462.1°C at 760 mmHg
• PKA: 3.93±0.21(Predicted)
• Flash Point: 233.3°C
• Density: 1.231g/cm³
• Storage Temp.: Store at 0°C
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 261.12123733
• Heavy Atom Count: 18
• Complexity: 320

Purity/Quality:

99.3% ^*data from raw suppliers

Boc-L-2-aminoadipicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (S)-2-((tert-Butoxycarbonyl)amino)hexanedioic acid

There total 8 articles about (S)-2-((tert-Butoxycarbonyl)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: 100.0%

L-homoglutamic acid (1118-90-7) + di-tert-butyl dicarbonate (24424-99-5) → Nα-(tert-butoxycarbonyl)-L-α-aminoadipic acid (77302-72-8)

Guidance literature:

With triethylamine; In water; N,N-dimethyl-formamide; for 1h;

DOI:10.1021/ja209018u

Reference yield: 95.0%

(+)-(S)-N2,N6-bis[(1,1-dimethylethoxy)carbonyl]-6-oxo-lysine methyl ester (97347-42-7) → Nα-(tert-butoxycarbonyl)-L-α-aminoadipic acid (77302-72-8)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 1h;

Reference yield: 95.0%

(S)-2,6-Bis-tert-butoxycarbonylamino-6-oxo-hexanoic acid 2,2,2-trichloro-ethyl ester (110545-04-5) → Nα-(tert-butoxycarbonyl)-L-α-aminoadipic acid (77302-72-8)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 1h;

upstream raw materials:

L-homoglutamic acid

di-tert-butyl dicarbonate

(S)-2-tert-Butoxycarbonylamino-5-(pyridin-2-ylsulfanyl)-hexanedioic acid 1-benzyl ester 6-methyl ester

(+)-(S)-N₂,N₆-bis[(1,1-dimethylethoxy)carbonyl]-6-oxo-lysine methyl ester

Downstream raw materials:

(S)-2-((tert-butoxycarbonyl)amino)-6-hydroxyhexanoic acid

(S)-5-((R)-2-Benzhydrylsulfanyl-1-carboxy-ethylcarbamoyl)-2-tert-butoxycarbonylamino-pentanoic acid 4-methoxy-benzyl ester

N-tert-butyloxycarbonyl-L-α-aminoadipic acid α-p-methoxybenzyl ester

L-homoglutamic acid

Refernces

• 1、 De Cat, Inge,Gobbo, Cristian,Van Averbeke, Bernard,Lazzaroni, Roberto,De Feyter, Steven,Van Esch, Jan. "Controlling the position of functional groups at the liquid/solid interface: Impact of molecular symmetry and chirality". supporting information; experimental part. p. 20942 - 20950. Retrieved 2012/02/13.
• 2、 Elkins, Jonathan M.,Rutledge, Peter J.,Burzlaff, Nicolai I.,Clifton, Ian J.,Adlington, Robert M.,Roach, Peter L.,Baldwin, Jack E.. "Crystallographic studies on the reaction of isopenicillin N synthase with an unsaturated substrate analogue". . p. 1455 - 1460. Retrieved 2007/10/03.