N-Biotinyl-1,6-hexanediamine

Base Information

• Chemical Name: N-Biotinyl-1,6-hexanediamine
• CAS No.: 65953-56-2
• Molecular Formula: C16H30N4O2S
• Molecular Weight: 342.506
• DSSTox Substance ID: DTXSID30455983
• Wikidata: Q82278169
• Mol file: 65953-56-2.mol

Synonyms:65953-56-2;N-Biotinyl-1,6-hexanediamine;N-(6-Aminohexyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide;5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-(6-aminohexyl)pentanamide;Biotinyl hexylamine;5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl]-N-(6-aminohexyl)pentanamide;SCHEMBL3066083;(N-biotinyl)hexamethylenediamine;DTXSID30455983;MFCD09264744;AKOS024464471;GS-5683;(3aS,4S,6aR)-N-(6-Aminohexyl)hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanamide;H10053;A867564

Chemical Property of N-Biotinyl-1,6-hexanediamine

Chemical Property:

• Melting Point: 184-186°C
• Boiling Point: 655.0±50.0 °C(Predicted)
• PKA: 13.90±0.40(Predicted)
• PSA: 128.53000
• Density: 1.116±0.06 g/cm3(Predicted)
• LogP: 2.85690
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 342.20894739
• Heavy Atom Count: 23
• Complexity: 394

Purity/Quality:

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

N-Biotinyl-1,6-hexanediamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(C(S1)CCCCC(=O)NCCCCCCN)NC(=O)N2
• Isomeric SMILES: C1[C@H]2[C@@H]([C@@H](S1)CCCCC(=O)NCCCCCCN)NC(=O)N2
• Uses: Intermediate in the preparation of serum biotinidase resistant Biotin derivatives used to make pretargeted diagnosis of tumors.

Technology Process of N-Biotinyl-1,6-hexanediamine

There total 12 articles about N-Biotinyl-1,6-hexanediamine 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%

tert-butyl (6-(5-((3aS,4S,6aR)-3a,6a-dimethyl-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)hexyl)carbamate (153162-70-0) → N-(6-aminohexyl)-5-((3aS,4S,6aR)-3a,6a-dimethyl-2-oxohexahydro-1H-thieno[3,4-d] imidazol-4-yl)pentanamide (65953-56-2)

Guidance literature:

With trifluoroacetic acid; for 0.0833333h; Sonication;

DOI:10.1021/jm800099g

Reference yield: 99.0%

1,6-Hexanediamine (124-09-4) + biotin (58-85-5,22879-79-4) → N-(6-aminohexyl)-5-((3aS,4S,6aR)-3a,6a-dimethyl-2-oxohexahydro-1H-thieno[3,4-d] imidazol-4-yl)pentanamide (65953-56-2)

Guidance literature:

biotin; With di(succinimido) carbonate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 6h; Inert atmosphere;

1,6-Hexanediamine; In N,N-dimethyl-formamide; Inert atmosphere;

DOI:10.1039/b906125h

Reference yield: 90.0%

1,6-Hexanediamine (124-09-4) + D-(+)-biotin 2-nitrophenyl ester (33755-53-2) → N-(6-aminohexyl)-5-((3aS,4S,6aR)-3a,6a-dimethyl-2-oxohexahydro-1H-thieno[3,4-d] imidazol-4-yl)pentanamide (65953-56-2)

Guidance literature:

With pyridine; In water; at 20 ℃; for 24h;

DOI:10.1016/j.bmc.2009.09.009

upstream raw materials:

tert-butyl (6-(5-((3aS,4S,6aR)-3a,6a-dimethyl-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)hexyl)carbamate

N-(tert-butoxycarbonyl)-1,6-diaminohexane hydrochloride

biotin

1,6-Hexanediamine

Downstream raw materials:

4-benzoyl-N-(5-(4-methoxybenzamido)-6-oxo-6-(6-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)hexylamino)hexyl)benzamide

4-benzoyl-N-(6-oxo-6-(6-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)-hexylamino)-5-(4-sulfamoylbenzamido)hexyl)benzamide

tert-butyl-6-(4-benzoylbenzamido)-1-oxo-1-(6-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)-pentanamido)hexylamino)hexan-2-ylcarbamate

C₇₉H₁₀₄N₆O₁₈S

Refernces

• 1、 -. "Tumor targeting metal complex, synthetic method and application". . . Retrieved 2017/07/21.
• 2、 Brglez, Josipa,Ahmed, Ishtiaq,Niemeyer, Christof M.. "Photocleavable ligands for protein decoration of DNA nanostructures". supporting information. p. 5102 - 5104. Retrieved 2015/05/13.