6-Tritylmercapto-hexanoic acid

Base Information

• Chemical Name: 6-Tritylmercapto-hexanoic acid
• CAS No.: 80441-55-0
• Molecular Formula: C25H26 O2 S
• Molecular Weight: 390.546
• Hs Code.: 29163990
• Mol file: 80441-55-0.mol

Synonyms:6-Tritylsulfanylhexanoicacid

Chemical Property of 6-Tritylmercapto-hexanoic acid

Chemical Property:

• Boiling Point: 536.7±38.0 °C(Predicted)
• PKA: 4.77±0.10(Predicted)
• PSA: 62.60000
• Density: 1.147±0.06 g/cm3(Predicted)
• LogP: 6.35670

Purity/Quality:

99% ^*data from raw suppliers

6-(Tritylthio)-hexanoic acid 95% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Description: 6-(Tritylthio)hexanoic acid is a linker with a Tst group and a terminal carboxylic acid. The Tst group can be deprotected under acidic conditions to obtain the free thiol which can be used for further conjugations. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond.

Technology Process of 6-Tritylmercapto-hexanoic acid

There total 6 articles about 6-Tritylmercapto-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: 95.0%

6-bromohexanoic acid (4224-70-8) + triphenylmethanethiol (3695-77-0) → 6-(S-tritylmercapto)hexanoic acid (80441-55-0)

Guidance literature:

triphenylmethanethiol; With sodium methylate; In methanol; acetonitrile; for 0.25h;

6-bromohexanoic acid; In tetrahydrofuran; methanol; acetonitrile; at 20 ℃; for 18h; Further stages.;

DOI:10.1016/j.tetlet.2007.04.123

Reference yield:

hexahydro-2H-oxepin-2-one (502-44-3,24980-41-4,80137-66-2) → 6-(S-tritylmercapto)hexanoic acid (80441-55-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / conc. HBr, conc. H₂SO₄ / 10 h / Heating

2: 66 percent / K₂CO₃ / ethanol / 12 h / Heating

With sulfuric acid; hydrogen bromide; potassium carbonate; In ethanol;

DOI:10.1021/ja00369a041

Reference yield:

ethyl 6-(tritylthio)-1-hexanoate (1329674-85-2) → 6-(S-tritylmercapto)hexanoic acid (80441-55-0)

Guidance literature:

With lithium hydroxide; In methanol; at 40 ℃; for 6h; Inert atmosphere;

DOI:10.1021/ja108807j

upstream raw materials:

6-bromohexanoic acid

triphenylmethanethiol

hexahydro-2H-oxepin-2-one

ethyl 6-(tritylthio)-1-hexanoate

Downstream raw materials:

(S)-N-(4-(2-(2,2,2-trifluoro-N-methylacetamido)propyl)phenyl)-6-(tritylthio)hexanamide

(S)-6-mercapto-N-(4-(2-(methylamino)propyl)phenyl)hexanamide

C₄₇H₄₈N₂O₂S

Refernces

• 1、 Moreno, Amira Y.,Mayorov, Alexander V.,Janda, Kim D.. "Impact of distinct chemical structures for the development of a methamphetamine vaccine". supporting information; experimental part. p. 6587 - 6595. Retrieved 2011/06/27.
• 2、 -. "FK228 analogs and methods of making and using the same". Page/Page column 23; 24; sheet 6. . Retrieved 2010/11/08.