1350889-86-9

Upstream product

• 415726-81-7 (2R,3R,4S,6R)-2,3:4,5-bis(isopropylidenedioxy)-1-cyclohexanone 
• 488-73-3 (+)-proto-quercitol 
• 98-88-4 benzoyl chloride 
• 1157852-09-9 1,2:3,4-di-O-isopropylidene-5R-(+)-proto-quercitol 

Downstream Products

• 1350889-88-1 C₁₇H₁₈Br₂O₄ 
• 1350889-89-2 C₂₄H₂₃BrO₆ 
• 442851-90-3 (1R,2S,3S,4S)-5-hydroxymethyl-1-octylamino-2,3,4-trihydroxycyclohex-5-ene 
• 1350889-87-0 C₁₇H₁₈O₄ 
• 1393710-16-1 2,6-di-O-benzoyl-3,4-O-isopropylidene-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide 
• 1425499-45-1 2-O-benzoyl-3,4-O-isopropylidene-6-methyl-6-deoxy-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide 
• 1425499-48-4 N-octyl-6-methyl-6-deoxy-5a-carba-α-L-arabino-hex-5(5a)-enopyranosylamine hydrochloride 
• 1393710-14-9 2-O-benzoyl-3,4-O-isopropylidene-6-bromo-6-deoxy-5a-carba-β-L-arabino-hex-5(5a)-enopyranosyl bromide 
• 1393710-15-0 2-O-benzoyl-3,4-O-isopropylidene-6-bromo-6-deoxy-5a-carba-α-L-arabino-hex-5(5a)-enopyranosyl bromide 

Relevant academic research and scientific papers

Concise syntheses of potent chaperone drug candidates, N-octyl-4-epi- β-valinenamine (NOEV) and its 6-deoxy derivative, from (+)-proto-quercitol

Described are the efficient syntheses of β-galactose-type unsaturated carbasugar amine, N-octyl-4-epi-β-valienamine (1a, NOEV) and 6-deoxy NOEV (12), starting from (+)-proto-quercitol (2), which is readily provided by the bioconversion of myo-inositol. NOEV is a potent chemical chaperone drug candidate for GM1-gangliosidosis. An intermediate alkadiene benzoate was prepared from 2 in five steps, with the key step being a Wittig reaction with an enol ester. The 6-deoxy derivative 12 was conveniently synthesized from the versatile intermediate dibromo compound 6, which was also an intermediate in the synthesis of NOEV. Enzyme inhibition assays demonstrated that 12 possessed stronger inhibitory activity than the parent 1a, suggesting that the C-6 position of the 4-epi-β-valienamine-type inhibitor could have hydrophobic interactions at the β-galactosidase active site residues.

Transformation of quercitols into 4-methylenecyclohex-5-ene-1,2,3-triol derivatives, precursors for the chemical chaperones N-octyl-4-epi-β- valienamine (NOEV) and N-octyl-β-valienamine (NOV)

(+)-proto-Quercitol (1) and (-)-vibo-quercitol (2), both of which could be readily prepared by the bioconversion of myo-inositol, were successfully converted into the corresponding 4-methylenecyclohex-5-ene-1,2,3-triol derivatives. These compounds were demonstrated to be suitable precursors, preserving their configurations, for bioactive carba-aminosugars such as the potent chemical chaperone drug candidates, N-octyl-4-epi-β-valienamine (NOEV, 3) and N-octyl-β-valienamine (NOV, 4).