115652-08-9

Upstream product

• 76521-35-2 N-<2-(acetylamino)-2-deoxy-3,4,6-triacetyl-β-D-glucopyranosyl>-N²-<(1,1-dimethylethoxy)carbonyl>-L-asparagine 
• 84010-54-8 phenylalanine 1,3-dithian-2-ylmethyl ester 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 57680-14-5 N-tert-Butyloxycarbonyl-L-asparaginsaeure-β-phenacylester 
• 115652-01-2 N⁴-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N²-(tert-butyloxycarbonyl)asparagine 1,3-dithian-2-ylmethyl ester 
• 115651-99-5 N-(tert-butyloxycarbonyl)aspartic acid β-phenacyl α-(1,3-dithian-2-ylmethyl)diester 
• 115652-00-1 N-(tert-butyloxycarbonyl)aspartic acid α-(1,3-dithian-2-ylmethyl) ester 

Relevant academic research and scientific papers

1,3-Dithian-2-ylmethyl Esters as Two-Step Carboxy-Protecting Groups in the Synthesis of N-Glycopeptides

The synthesis of totally protected N-acetylglucosaminylasparagine glycopeptides using the 1,3-dithian-2-ylmethyl (Dim) ester for selective C-terminal deprotection is described.Dim esters of amino acids can be conveniently synthesized by aluminum isopropoxide catalyzed transesterification of amino acid methyl esters with 1,3-dithian-2-ylmethanol or esterification of Boc amino acids with this alcohol followed by selective cleavage of the Boc group under acidic conditions.For the construction of N-glycopeptides Boc-asparatic acid α-Dim ester was synthesized and condensed with 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosylamine.The Dim group was cleaved under very mild conditions (pH 8) after oxidation of sulfur in the dithiane ring.During this reaction the Boc group, the O-acetates, and the glycoside bond remained intact.The selectively deblocked glycosylated asparagine thus obtained was condensed with amino acid Dim esters to yield totally protected glycodipeptides in high yields.