291314-22-2

Upstream product

• 77196-31-7 2-(dimethoxymethyl)naphthalene 
• 17791-36-5 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 
• 66-99-9 β-naphthaldehyde 
• 100-39-0 benzyl bromide 
• 291314-21-1 methyl 4,6-O-((2-naphthyl)methylene)-α-D-glucopyranoside 
• 2641-79-4 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside 
• 104-88-1 4-chlorobenzaldehyde 
• 100-52-7 benzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 1122-91-4 4-bromo-benzaldehyde 
• 106-95-6 allyl bromide 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 824-94-2 p-methoxybenzyl chloride 

Downstream Products

• 291314-27-7 methyl 2,3-di-O-benzyl-4-O-(2-naphthyl)methyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

METHOD FOR PREPARING HEXOSE DERIVATIVES

A method for preparing hexose derivatives comprises the steps of providing a silylated hexose, treating the silylated hexose with a first carbonyl compound in the presence of a catalyst to form an ketalized hexose, treating the ketalized hexose with a second carbonyl compound followed by treating with a first reductant to form an etherized hexose, and converting the etherized hexose into a target hexose derivative, which can be 2-alcohol hexose, 3-alcohol hexose, 4-alcohol hexose, or a 6-alcohol hexose. In particular, the present invention can prepare the hexose derivatives with highly regioselective scheme to protect individual hydroxyls of monosaccharide units and install an orthogonal protecting group pattern in a one-pot manner

Dioxane-type (2-naphthyl)methylene acetals of glycosides and their hydrogenolytic transformation into 6-O- and 4-O-(2-naphthyl)methyl (NAP) ethers

α-, β-D-Gluco-, galacto-, 2-deoxy-2-phthalimido-β-D-glucopyranosides with different aglycons (methyl, allyl, p-methoxyphenyl, thioethyl) reacted with 2-naphthaldehyde dimethyl acetal to give rise to 4,6-O-(2-naphthyl)methylene acetals. The acetals were converted into fully protected compounds bearing benzoyl, benzyl, allyl, p-methoxybenzyl groups. The fully alkylated dioxane-type acetals were hydrogenolysed with AlH3 (3LiAlH4-AlCl3) reagent to furnish 4-O-NAP/6-OH derivatives. All acetals were treated with BH3·Me3N-AlCl3 in THF and a reverse regioselectivity was observed, producing 6-O-NAP/4-OH derivatives. Similar regioselectivity was also observed by using NaCNBH3-HCl reagent. In all reactions very mild reaction conditions were required, regioselectivity was better than 93:7, and the isolated yields were between 83-92%. All compounds were characterised by 1H and 13C NMR spectra. Solid-state and solution conformation of methyl 2,3-di-O-acetyl-4,6-O-(2-naphthyl)methylene-α-D-galactopyranoside were elucidated by X-ray and NMR measurements.

Preparation of (2-naphthyl)methylene acetals of glycosides and their hydrogenolytic transformation into 2-naphthylmethyl (NAP) ethers

Dioxane- and dioxolane-type (2-naphthyl)methylene acetals of glycosides were prepared by acid-catalyzed transacetalization reactions. The acetals were cleaved using either AlH3 (LiAlH4:AlCl3-3:1), NaCNBH3-HCl or BH3·Me3N-AlCl3 reagents. Reaction of the 4,6-O-acetals with AlH 3 yielded 4-ONAP ethers whereas the other two reagents gave 6-ONAP derivatives with excellent regioselectivity. In dioxolane, type acetals the direction of the cleavage with all three reagents is determined by the stereochemistry of the acetal center; equatorial ONAP/axial-hydroxy derivatives are obtained from the exo-naphthyl isomers; endo-naphthyl acetals, on the other hand, give rise to the formation of axial ONAP/equatorial-hydroxy compounds. The NAP ether and the (2-naphthyl)methylene acetal protecting groups can both be readily removed by treatment with DDQ. (C) 2000 Elsevier Science Ltd.