Nepsilon-Carbobenzoxy-Nalpha-tosyl-L-lysine

Base Information

• Chemical Name: Nepsilon-Carbobenzoxy-Nalpha-tosyl-L-lysine
• CAS No.: 34235-82-0
• Molecular Formula: C21H26N2O6S
• Molecular Weight: 434.513
• Hs Code.: 2935009090
• DSSTox Substance ID: DTXSID50555575
• Nikkaji Number: J208.204G
• Wikidata: Q82436965
• Mol file: 34235-82-0.mol

Synonyms:34235-82-0;Nepsilon-Carbobenzoxy-Nalpha-tosyl-L-lysine;Tos-Lys(Z)-OH;(S)-6-(((Benzyloxy)carbonyl)amino)-2-(4-methylphenylsulfonamido)hexanoic acid;(2S)-2-[(4-methylphenyl)sulfonylamino]-6-(phenylmethoxycarbonylamino)hexanoic acid;N|A-Carbobenzoxy-N|A-tosyl-L-lysine;Nalpha-Tosyl-Nepsilon-Z-L-lysine;N-(Epsilon)-carbobenzoxy-N-(alpha)-tosyl-L-lysine;SCHEMBL10365919;DTXSID50555575;XSWGRGGVKUEBSE-IBGZPJMESA-N;Nepsilon-Cbz-Nalpha-tosyl-L-lysine;MFCD00059201;AKOS027321015;HY-W141974;AS-46899;CS-0201764;F10854;A875062;(S)-6-(benzyloxycarbonylamino)-2-(4-methylphenylsulfonamido)hexanoic acid;N (epsilon)-CarbobenZoxy-N (alpha)-tosyl-L-lysine (Tos-L-Lys(CbZ)-OH);N~6~-[(Benzyloxy)carbonyl]-N~2~-(4-methylbenzene-1-sulfonyl)-L-lysine;(2S)-6-{[(benzyloxy)carbonyl]amino}-2-{[(4-methylphenyl)sulfonyl]amino}hexanoic acid

Chemical Property of Nepsilon-Carbobenzoxy-Nalpha-tosyl-L-lysine

Chemical Property:

• Melting Point: 123 °C
• Refractive Index: 14.5 ° (C=1, EtOH)
• PSA: 130.18000
• LogP: 4.68580
• Storage Temp.: 2-8°C
• Solubility.: almost transparency in hot Toluene
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 434.15115773
• Heavy Atom Count: 30
• Complexity: 634

Purity/Quality:

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

Nepsilon-carbobenzoxy-N-α-Tosyl-L-Lysine ^*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)NC(CCCCNC(=O)OCC2=CC=CC=C2)C(=O)O
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)N[C@@H](CCCCNC(=O)OCC2=CC=CC=C2)C(=O)O

Technology Process of Nepsilon-Carbobenzoxy-Nalpha-tosyl-L-lysine

There total 11 articles about Nepsilon-Carbobenzoxy-Nalpha-tosyl-L-lysine 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: 78.0%

(2S)-2-tosylamino-6-benzyloxycarbonylaminohexanol (912806-85-0) → N-tosyl-N'-benzyloxycarbonyl-L-lysine (34235-82-0)

Guidance literature:

With jones' reagent; In acetone; at 0 - 20 ℃; for 8h;

DOI:10.1016/j.tet.2006.07.024

Reference yield:

N6-[(benzyloxy)carbonyl]-L-lysine (1155-64-2,57705-97-2,67178-46-5,25931-47-9) + p-toluenesulfonyl chloride (98-59-9) → N-tosyl-N'-benzyloxycarbonyl-L-lysine (34235-82-0)

Guidance literature:

DOI:10.1039/jr9570003134

Reference yield:

4-[2-oxo-3-(toluene-4-sulfonyl)-oxazolidin-4-yl]-butyraldehyde → N-tosyl-N'-benzyloxycarbonyl-L-lysine (34235-82-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine / tetrahydrofuran / 0.17 h / 0 °C

1.2: sodium cyanoborohydride / tetrahydrofuran / 8 h / 0 - 20 °C

2.1: 99 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 9 h / 20 °C

3.1: hydrogen / Pd(OH)2/C / methanol / 8.5 h / 20 °C / 760 Torr

4.1: potassium carbonate / tetrahydrofuran; H₂O / 0 - 20 °C

5.1: 78 percent / Jones' reagent / acetone / 8 h / 0 - 20 °C

With lithium hydroxide; jones' reagent; hydrogen; potassium carbonate; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; water; acetone;

DOI:10.1016/j.tet.2006.07.024

upstream raw materials:

N₆-[(benzyloxy)carbonyl]-L-lysine

p-toluenesulfonyl chloride

(2S)-2-tosylamino-6-benzyloxycarbonylaminohexanol

(E)-N-tosyl-4-(4',4'-diethoxybutylidene)-1,3-oxazolidin-2-one

Downstream raw materials:

(S)-methyl 6-(((benzyloxy)carbonyl)amino)-2-(4-methylphenylsulfonamido)hexanoate

4-{[N⁶-benzyloxycarbonyl-N²-(toluene-4-sulfonyl)-L-lysyl]-amino}-benzoic acid benzyl ester

D-Allosaccharopin

L-Saccharopine

Refernces

• 1、 Shen, Zengming,Lu, Xiyan,Lei, Aiwen. "Highly enantioselective hydrogenation of exocyclic double bond of N-tosyloxazolidinones catalyzed by a neutral rhodium complex and its synthetic applications". . p. 9237 - 9246. Retrieved 2007/10/03.