(S)-2-((tert-Butoxycarbonyl)amino)-6-(4-methylphenylsulfonamido)hexanoic acid

Base Information

• Chemical Name: (S)-2-((tert-Butoxycarbonyl)amino)-6-(4-methylphenylsulfonamido)hexanoic acid
• CAS No.: 13734-29-7
• Molecular Formula: C18H28 N2 O6 S
• Molecular Weight: 400.496
• Hs Code.: 2935009090
• DSSTox Substance ID: DTXSID80365841
• Mol file: 13734-29-7.mol

Synonyms:13734-29-7;(S)-2-((tert-Butoxycarbonyl)amino)-6-(4-methylphenylsulfonamido)hexanoic acid;Boc-Lys(Tos)-OH;Boc-Lys(Tos)-OH DCHA;(2S)-6-[(4-methylphenyl)sulfonylamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid;DTXSID80365841;HSTSERPPSSLPFN-HNNXBMFYSA-N;MFCD00038261;(S)-2-((tert-Butoxycarbonyl)amino)-6-(4-methylphenylsulfonamido)hexanoicacid;AKOS016843147;CS-0445631;N2-(tert-butoxycarbonyl)-N6-tosyl-L-lysine;(S)-2-(tert-butoxycarbonylamino)-6-(4-methylphenylsulfonamido)hexanoic acid;(2S)-2-{[(tert-butoxy)carbonyl]amino}-6-(4-methylbenzenesulfonamido)hexanoic acid;N-alpha-t-Butyloxycarbonyl-N-epsilon-p-tolylsulfonyl-L-lysine (Boc-L-Lys(Tos)-OH)

Chemical Property of (S)-2-((tert-Butoxycarbonyl)amino)-6-(4-methylphenylsulfonamido)hexanoic acid

Chemical Property:

• PKA: 3.98±0.21(Predicted)
• PSA: 130.18000
• Density: 1.218±0.06 g/cm3(Predicted)
• LogP: 4.28410
• Storage Temp.: 2-8°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 400.16680779
• Heavy Atom Count: 27
• Complexity: 586

Purity/Quality:

98%min ^*data from raw suppliers

N-alpha-Boc-Nε-4-toluenesulfonyl-L-lysine dicyclohexylammonium salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NCCCCC(C(=O)O)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)NCCCC[C@@H](C(=O)O)NC(=O)OC(C)(C)C
• Uses: BOC-LYS(TOS)-OH DCHA (CAS# 13734-29-7) is an amino acid derivative used in the preparation of peptides, such as those with glycine or lysylglycine esters. BOC-LYS(TOS)-OH DCHA has also been used in the synthesis of selective vasopressin hypotensive agonist peptides.

Technology Process of (S)-2-((tert-Butoxycarbonyl)amino)-6-(4-methylphenylsulfonamido)hexanoic acid

There total 2 articles about (S)-2-((tert-Butoxycarbonyl)amino)-6-(4-methylphenylsulfonamido)hexanoic 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:

di-tert-butyl dicarbonate (24424-99-5) + (S)-2-amino-6-(4-methylphenylsulfonamido)hexanoic acid (2130-76-9) → Nα-tert-butoxycarbonyl-Nε-tosyl-L-lysine (13734-29-7)

Guidance literature:

With triethylamine;

DOI:10.1007/BF00565050

Reference yield:

1,1-dimethylethyl 2,4,5-trichlorophenyl carbonate (16965-08-5) + (S)-2-amino-6-(4-methylphenylsulfonamido)hexanoic acid (2130-76-9) → Nα-tert-butoxycarbonyl-Nε-tosyl-L-lysine (13734-29-7)

Guidance literature:

With triethylamine; In tert-butyl alcohol;

DOI:10.1039/j39670002632

Reference yield: 99.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + Nα-tert-butoxycarbonyl-Nε-tosyl-L-lysine (13734-29-7) → Nα-tert-butoxycarbonyl-Nε-tosyl-L-lysine methyl ester (99532-85-1)

Guidance literature:

DOI:10.1021/ja00261a023

upstream raw materials:

di-tert-butyl dicarbonate

(S)-2-amino-6-(4-methylphenylsulfonamido)hexanoic acid

1,1-dimethylethyl 2,4,5-trichlorophenyl carbonate

Downstream raw materials:

N^α-tert-butoxycarbonyl-N^ε-tosyl-L-lysine methyl ester

1-α-O-benzyl-4,6-O-benzylidene-N-acetylnormuramyl-α-aminobutyryl-D-isoglutaminyl-N^ε-p-toluenesulfonyllysyl-N^ε-p-toluenesulfonyllysyl-N^ε-p-tolueunesulfonyllysine amide

Boc-Lys(Ts)-Lys(Ts)-Gly-OMe

Boc-Lys-OH

Refernces