192059-40-8

Upstream product

• 616876-80-3 (S)-2-Phenyl-[1,3]dioxane-4-carboxylic acid (S)-2-phenyl-[1,3]dioxan-4-ylmethyl ester 
• 256390-84-8 (S)-4-(hydroxymethyl)-2-phenyl-1,3-dioxane 
• 286856-62-0 (S)-2-Phenyl-[1,3]dioxane-4-carboxylic acid tert-butyl ester 

Downstream Products

• 192059-61-3 methyl 3-O-benzyl-4-(2,4-O-benzylidene-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-3-O-benzyl-4-(2,4-O-benzylidene-3-deoxy-L-glycero-tetronamido)-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-3-O-benzyl-... 

Relevant academic research and scientific papers

New N-acylating reagents derived from 3-deoxy-L-glycero-tetronic acid

Commercially available N-Boc-4-O-benzyl-L-homoserine was treated with trifluoroacetic acid and the corresponding, N-deprotected derivative was submitted to deamination to give 4-O-benzyl-3-deoxy-L-glycero-tetronic acid (5). In another approach to 3-deoxy-L-glycero-tetronic acid protected at position 4, the carboxylic groups in L-malic acid were reduced, and the resulting triol was benzylidenated. Oxidation of the 2,4-O-benzylidene derivative formed with CrO3-pyridine complex in the presence of t-butyl alcohol gave t-butyl 2,4-O-benzylidene-3-deoxy-L-glycero-tetronate (13). The latter was saponified with aqueous sodium hydroxide to give, after Na+ exchange for H+, 2,4-O-benzylidene-3-deoxy-L-glycero-tetronic acid (15). Opening of the acetal ring in 13, followed by hydrolytic cleavage of the t-butyl ester function gave material indistinguishable from 5 obtained in the original way. When tested for their efficiency of N-acylation of derivatives of D-perosamine, both acids 5 and 15 gave the corresponding tetronamido derivatives in high yields.