4119-19-1

Upstream product

• 76-83-5 trityl chloride 
• 79083-42-4 methyl D-arabinofuranoside 
• 1252031-92-7 C₂₅H₂₆O₅ 
• 100-39-0 benzyl bromide 
• 10323-20-3 D-Arabinose 
• 4060-35-9 methyl 5-O-trityl-α-D-arabinofuranoside 

Downstream Products

• 16896-03-0 methyl 2,3-di-O-benzyl-α-D-arabinofuranoside 
• 53458-72-3 methyl 2,3-di-O-benzyl-5-O-p-toluenesulfonyl-α-D-arabinofuranoside 
• 697298-49-0 methyl 2,3-di-O-benzyl-5-deoxy-5-diethylphosphonomethyl-α-D-arabinofuranoside 
• 404935-69-9 (2S,3S,4S,5S)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-carboxylic acid (R)-1-vinyl-decyl ester 
• 404935-68-8 (2S,3S,4S,5S)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-carboxylic acid (S)-1-vinyl-decyl ester 
• 404935-57-5 (2S,3S,4S,5S)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-carboxylic acid 1-vinyl-decyl ester 
• 404935-58-6 (2S,3S,4S,5S)-3,4-Bis-benzyloxy-5-methoxy-tetrahydro-furan-2-carboxylic acid 
• 697298-48-9 methyl 2,3-di-O-benzyl-5-dehydro-α-D-arabinofuranoside 

Relevant academic research and scientific papers

Arabino mycolates from synthetic mycolic acids

The synthesis of single mono-arabino mycolates, important lipid antigens from mycobacteria is described, using structurally defined synthetic mycolic acids. Preliminary assays indicate that these are differentially antigenic to antibodies in the serum of

Synthesis of partially benzylated arabinofuranosides, NMR analysis, and application to oligosaccharide synthesis

The preparation and NMR analysis of 2,3-di-O-benzyl arabinofuranosides have been described. In DMSO-d6, the sugar adopts a conformation in which the hydroxyl groups are in an equatorial position; the equilibrium composition is determined by steric factors. In CDCl3, the sugar adopts a conformation in which the intramolecular hydrogen bonding plays an important role in determining the equilibrium composition. The use of 2,3-di-O-benzyl arabinose in the synthesis of oligoarabinofuranosides enabled the synthesis of α- or β-linked furanosides.

Enantiospecific synthesis of the phospholipase A2 inhibitor (-)-cinatrin B

The first enantiospecific synthesis of phospholipase A2 (PLA2) inhibitor (-)-cinatrin B (2) from the D-arabinose derivative 9 is described. The spirolactone system was formed by an Ireland-Claisen rearrangement of the allyl ester 8 followed by hydrolysis and stereoselective iodolactonization. The stereoselectivity of the rearrangement was controlled by the asymmetry in the allylic alcohol fragment. Ester (S)-8 gave the desired rearrangement product 7 and the epimer 13 in high yield as a 73:27 ratio, respectively. The final stereocenter at C2 was introduced via a chelation-controlled addition of the Grignard reagent derived from trimethylsilylacetylene to α-hydroxy ketone 6. Transformation of the terminal alkyne into the methyl ester 21 followed by acetal hydrolysis and selective lactol oxidation afforded cinatrin B methyl ester (22). Base hydrolysis and acid-induced relactonization then gave (-)-cinatrin B (2).