90318-59-5

Upstream product

• 85464-51-3 (2R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 2880-95-7 methyl (methyl 3-deoxy-α-D-arabino-2-heptulopyranosid)onate 
• 90318-58-4 diphenyl 7-phosphate 

Downstream Products

• 90318-60-8 (methyl 3-deoxy-D-arabino-2-heptulopyranosid)onic acid dihydrogen 7-phosphate 

Relevant academic research and scientific papers

A novel chemical synthesis of a 3-deoxy-D-arabino-heptulosonic acid 7-phosphate (DAHP) derivative and its 2-deoxy analogue

Using 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl cyanide as a precursor, methyl (methyl 3-deoxy-α-D-arabino-hept-2-ulopyranosid)onate (6) and its 2-deoxy analogue (10) were prepared. The synthesis involved an elimination of one molecule of acetic acid from C-2-C-3 and transformation of the CN group into COOMe, followed by methoxymercuration with subsequent reductive removal of the mercuri residue to give 6 or hydrogenation of the double bond to give 10. Phosphorylation of the 7-OH group led to the title compounds.

SYNTHESIS OF 3-DEOXY-D-arabino-2-HEPTULOSONIC ACID 7-PHOSPHATE BY PHOSPHORYLATION OF METHYL (METHYL 3-DEOXY-D-arabino-HEPTULOPYRANOSID)ONATE

3-Deoxy-D-arabino-2-heptulosonic acid 7-phosphate (5), the first committed intermediate in aromatic amino acid biosynthesis, has been synthesized in good yield by treatment of methyl(methyl 3-deoxy-D-arabino-2-heptulopyranosid)onate with diphenylphosphori