404377-28-2

Upstream product

• 404377-25-9 methyl 4,5,7-tri-O-benzyl-2-deoxy-D-gluco-hept-2-ulosonate diethyldithioacetal 
• 404377-35-1 methyl 3-O-acetyl-4,5,7-tri-O-benzyl-α-D-gluco-hept-2-ulopyranosonate 
• 136305-59-4 methyl 4,5,7-tri-O-benzyl-α-D-gluco-hept-2-ulopyranosonate 
• 160549-10-0 2,3,5-tri-O-benzyl-D-arabinofuranose 

Downstream Products

• 404377-32-8 methyl 2,4,5,7-tetra-O-benzyl-3-deoxy-α-D-arabino-2-heptulopyranosonate 
• 404377-30-6 methyl 2,4,5,7-tetra-O-benzyl-3-O-thiobenzoyl-α-D-gluco-2-heptulopyranosonate 

Relevant academic research and scientific papers

Efficient synthesis of 3-deoxy-D-arabino-2-heptulosonate (DAH) and -D-gluco-2-heptulosonate by a two-carbon chain elongation of D-arabinose

Reaction of α-lithiated methyl glyoxylate diethyl mercaptal (3) with 2,3,5-tri-O-benzyl-D-arabinose (2) stereoselectively afforded the D-gluco-2-heptulosonate derivative 4. Mercaptal cleavage led to the corresponding pyranose 5a which could be directly transformed into unprotected D-gluco-2-heptulosonic acid (1a), one of the target molecules. Deoxygenation of 5a at C-3 could also be readily accomplished as its 3-hydroxy group is unprotected. Thus, the second target molecule, 1b, was obtained in just a few steps.