178680-93-8

Upstream product

• 286856-62-0 (S)-2-Phenyl-[1,3]dioxane-4-carboxylic acid tert-butyl ester 
• 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 

Downstream Products

• 172471-74-8 4-O-benzyl-L-glycero-tetronic acid 
• 286856-65-3 t-butyl 2-O-acetyl-4-O-benzyl-3-deoxy-L-tetronate 

Relevant academic research and scientific papers

Syntheses of fluorinated ligands to probe binding of antigenic determinants of Vibrio cholerae O:1, serotypes Inaba and Ogawa, to antibodies

Derivatives of methyl α-glycosides of antigenic determinants of Vibrio cholerae O:1, serotypes Inaba and Ogawa, specifically fluorinated at position 2' or 4' have been synthesized by coupling the appropriately fluorinated derivatives of 3-deoxy-L-glycero-tetronic acid with the methyl α-glycosides of perosamine. The compound having the fluorine atom at position 2 was obtained by electrophilic addition of fluorine to the glycal derived from the parent antigenic determinant, serotypes Inaba, using Selectfluor((TM)) as a fluorination reagent. Copyright (C) 2000 Elsevier Science Ltd.

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.