442851-90-3

Upstream product

• 111-86-4 n-Octylamine 
• 177898-40-7 N-octyl-2,3:4,6-di-O-isopropylidene-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine 
• 415726-81-7 (2R,3R,4S,6R)-2,3:4,5-bis(isopropylidenedioxy)-1-cyclohexanone 
• 488-73-3 (+)-proto-quercitol 
• 1350889-89-2 C₂₄H₂₃BrO₆ 
• 1350889-88-1 C₁₇H₁₈Br₂O₄ 
• 1350889-87-0 C₁₇H₁₈O₄ 
• 1350889-86-9 C₃₀H₂₆O₈ 
• 1157852-09-9 1,2:3,4-di-O-isopropylidene-5R-(+)-proto-quercitol 
• 796850-44-7 C₂₈H₅₃NO₁₀ 
• 442852-00-8 N-octyl-N-tert-butoxycarbonyl-2,3-di-O-methoxymethyl-6-O-tert-butyldimethylsilyl-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine 
• 442851-98-1 N-octyl-N-tert-butoxycarbonyl-4,6-O-benzylidene-2,3-di-O-methoxymethyl-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine 
• 442852-09-7 ((3aS,4R,9aR,9bS)-2,8-Diphenyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-yl)-octyl-carbamic acid tert-butyl ester 
• 442851-96-9 N-octyl-N-tert-butoxycarbonyl-4,6-O-benzylidene-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine 

Relevant academic research and scientific papers

Novel stereoselective syntheses of N -octyl-β-valienamine (NOV) and N -octyl-4- epi -β-valienamine (NOEV) from (-)-shikimic acid

N-Octyl-β-valienamine (NOV) 1 and N-octyl-4-epi-β-valienamine (NOEV) 2 are potent chemical chaperone drug candidates for the therapy of lysosomal storage disorders. Novel stereoselective syntheses of NOV 1 and NOEV 2 starting from naturally abundant (-)-shikimic acid are described in this article. The common key intermediate compound 5 was first synthesized from readily available (-)-shikimic acid via 9 steps in 50% yield. Compound 5 was then converted to NOV 1via 5 steps in 61% yield, and it was also converted to NOEV 2via 8 steps in 38% yield. In summary, NOV 1 was synthesized via 14 steps in 31% overall yield; and NOEV 2 was synthesized via 17 steps in 19% overall yield.

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).

ACID ADDITION SALT OF CARBASUGAR AMINE DERIVATIVE

An acid addition salt of a carba-sugar amine derivative represented by the following formula (1): wherein R1 and R2 each independently represents a hydrogen atom, or an alkyl group, an alkenyl group, an alkynyl group, an acyl group,

Convenient synthesis and evaluation of glycosidase inhibitory activity of α- And β-galactose-type valienamines, and some N-alkyl derivatives

Valienamine analogues having α- and β-galactose-type structures were synthesized by racemic modification from (1SR,2RS,3SR)-6-methylenecyclohex- 4-ene-1,2,3-triol. Four N-alkyl derivatives of the β-anomer were readily prepared selectively by treatment of

CARBA-SUGAR AMINE DERIVATIVES AND TREATMENTS FOR DISORDER OF GLYCOLIPID METABOLISM CONTAINING THE SAME AS THE ACTIVE INGREDIENT

A carba-sugar amine derivative represented by the following formula (1) or (2) is used as the active ingredient of a β-galactosidase inhibitor or a glycolipid metabolic disorder treating agent. Wherein each of R1 and R2 independently

Chemical modification of the beta-glucocerebrosidase inhibitor N-octyl-beta-valienamine: synthesis and biological evaluation of 4-epimeric and 4-O-(beta-D-galactopyranosyl) derivatives.

N-Octyl-beta-valienemine (1), a potent beta-glucocerebrosidase inhibitor, was chemically transformed into two biologically interesting compounds: the 4-epimer, beta-galacto-type N-octyl-valienamine, and the 4-O-(beta-D-galactopyranosyl) derivative, a carba-lactosylceramide analogue. The former, interestingly, could be demonstrated to act as a very effective inhibitor (IC(50)=0.3 microM) of human beta-galactosidase. The latter exhibited moderate inhibitory activity (IC(50)=20 microM) against beta-glucocerebrosidase (mouse liver).