341972-47-2

Basic information

• Product Name: 4,5-dimethoxy-2-(triphenylmethylthio)benzylamine
• Synonyms: 4,5-dimethoxy-2-(triphenylmethylthio)benzylamine
• CAS NO: 341972-47-2
• Molecular Weight: 441.594
• Mol File: 341972-47-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4,5-dimethoxy-2-(triphenylmethylthio)benzylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-dimethoxy-2-(triphenylmethylthio)benzylamine(341972-47-2)
• EPA Substance Registry System: 4,5-dimethoxy-2-(triphenylmethylthio)benzylamine(341972-47-2)

Safety Data

• Hazardous Substances Data: 341972-47-2(Hazardous Substances Data)

Upstream product

• 76-84-6 triphenylmethyl alcohol 
• 21407-29-4 2-mercapto-4,5-dimethoxybenzylamine hydrochloride 
• 76-83-5 trityl chloride 

Downstream Products

• 475113-76-9 (4,5-dimethoxy-2-tritylsulfanyl-benzylamino)-acetic acid methyl ester 
• 920271-81-4 Fmoc-Gly(1-¹³C)-D,L-(4,5-dimethoxy-2-tritylthiobenzyl)-Ala-OH 
• 920271-77-8 Fmoc-Gly(1-¹³C)-D,L-(4,5-dimethoxy-2-tritylthiobenzyl)-Ala-OMe 
• 920271-86-9 Fmoc-Gly-D,L-(4,5-dimethoxy-2-tritylthiobenzyl)-Ala-OMe 
• 920271-78-9 Fmoc-Gly(1-¹³C)-D,L-(4,5-dimethoxy-2-mercaptobenzyl)-Ala-OMe 
• 920271-76-7 D,L-(4,5-dimethoxy-2-tritylthiobenzyl)Ala-OMe 

Relevant articles and documents

Peptide bond formation mediated by 4,5-dimethoxy-2-mercaptobenzylamine after periodate oxidation of the N-terminal serine residue.

[reaction in text] A thiol linker-attached peptide was prepared from a nonprotected peptide via an N(alpha)()-alpha-oxoacyl peptide. Selective oxidation of the N-terminal serine with sodium periodate gave the N(alpha)-glyoxyloyl peptide, reductive amination of which with 4,5-dimethoxy-2-(triphenylmethylthio)benzylamine gave an N(alpha)-4,5-dimethoxy-2-mercaptobenzyl glycyl peptide after removal of the trityl group. The N(alpha)-4,5-dimethoxy-2-mercaptobenzyl peptide can be condensed with a peptide thioester, and the linker is removable. This strategy provides a useful method for the synthesis of peptides using recombinant proteins.

Synthesis and application of an auxiliary group for chemical ligation at the X-gly site.

An efficient synthesis of an auxiliary group, the 2-mercapto-4,5-dimethoxybenzyl (Dmmb) moiety, to form a Gly-building block is presented. The building block was incorporated into peptides to study the reaction with thiobenzyl-activated derivatives. The target peptides have been obtained by standard chemical ligation reaction, followed by TMSBr-assisted cleavage to remove the auxiliary group. Prior to Dmmb removal, under acidic conditions an unexpected rearrangement was observed and evidence for a mechanism is provided.