65530-31-6

Upstream product

• 65530-27-0 (2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine 
• 71117-37-8 (2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 67-56-1 methanol 
• 1471283-58-5 C₁₆H₁₈O₆ 
• 2880-96-8 (1aR,2S,6R,7aR,7bR)-2-Methoxy-6-phenyl-hexahydro-1,3,5,7-tetraoxa-cyclopropa[a]naphthalene 
• 709-50-2 methyl beta-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 192769-48-5 methyl 4,6-O-benzylidene-2,3-O-thiocarbonyl-β-D-glucoside 

Downstream Products

• 74644-56-7 1,5-anhydro-3-azido-4,6-O-benzylidene-2,3-dideoxy-D-arabino-hex-1-enitol 
• 142632-74-4 methyl 4,6-O-benzylidene-2,3-dideoxy-β-D-erythro-hexopyranoside 
• 76231-52-2 O-benzylidene-4,6 tridesoxy-1,2,3 deuterio-3 D-arabino-hexeno-1 pyranose 
• 126924-12-7 Methyl 4,6-O-(phenylmethylene)-β-D-allopyranoside 
• 34366-99-9 methyl 2,3-dideoxy-4,6-di-O-p-toluenesulfonyl-β-D-glycero-hexopyranoside 
• 100102-49-6 Methyl-4-O-benzoyl-2,3,6-tridesoxy-β-D-erythro-hexopyranosid 
• 142573-20-4 methyl 2,3-dideoxy-6-O-p-toluenesulfonyl-β-D-erythro-hexopyranoside 
• 142573-09-9 methyl 4-O-benzoyl-6-bromo-2,3,6-trideoxy-β-D-erythro-hexopyranoside 
• 142573-12-4 methyl 4-O-(3,4-O-benzylidene-α-L-arabinopyranosyl)-2,3,6-trideoxy-β-D-erythro-hexopyranoside 
• 142573-22-6 methyl 2,3-di-deoxy-6-O-p-toluenesulfonyl-4-O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-erythro-hexopyranoside 
• 142573-13-5 methyl 4-O-<3,4-O-benzylidene-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-α-L-arabinopyranosyl>-2,3,6-trideoxy-β-D-erythro-hexopyranoside 
• 142573-21-5 methyl 4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-2,3-di-deoxy-6-O-p-toluenesulfonyl-β-D-erythro-hexopyranoside 
• 142573-25-9 methyl 2,3-dideoxy-4-O-<3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranosyl>-β-D-erythro-hexopyranoside 
• 142573-10-2 methyl 6-bromo-2,3,6-trideoxy-4-O-<3,4,6-tri-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-galactopyranosyl>-β-D-erythro-hexopyranoside 

Relevant academic research and scientific papers

Stereocontrolled O -glycosylation with palladium-catalyzed decarboxylative allylation

The Pd-π-allyl intermediate in an electron-rich glycal system with poor reactivity is employed as an efficient glycosyl donor. Starting from glucal derived carbonate, various O-glycosides were formed via a palladium-catalyzed reaction through a tandem decarboxylation, proton abstraction, and nucleophilic addition, in good yields with excellent selectivity. Iterative glycosylation with the same strategy may provide an access to complex oligosaccharides.

Kinetically controlled Ferrier rearrangement of 3-O-mesyl-d-glycal derivatives

The Ferrier rearrangement, which is widely used in carbohydrate chemistry, is generally performed under acidic conditions to give an α anomer with high stereoselectivity. We have found that 3-O-mesyl-d-glycals 2-4 were smoothly reacted with alcohols in th

Stereospecific synthesis of β-D-allopyranosides by dihydroxylation of β-D-erythro-2,3-dideoxyhex-2-enopyranosides

The synthesis of 4,6-O-benzylidene-β-D-erythro-2-3-dideoxyhex-2-enopyranosides and their osmium and ruthenium catalysed dihydroxylation reactions have been investigated. These reactions have been shown, for a range of monosaccharides and a disaccharide, to proceed stereospecifically to give β-D-allopyranosides in moderate to excellent yield.

Thio-sugars III. Radical catalyzed thione-thiol rearrangement of cyclic thionocarbonates on a pyranose ring: Formation of cis-arranged cyclic thiolcarbonates

Pyranoside 3,4-cis-thionocarbonates, under radical-promoted reaction conditions (method A, B, or C, described in the text), gave O-S rearrangement products, 3,4-thiolcarbonates of cis-stereochemistry, in acceptable yields. 2,3-Thionocarbonates of trans-stereochemistry also gave the rearrangement products of cis-stereochemistry preferentially in method B (photolysis with hexabutyldistannane). Although regio-control of the product was not satisfactory in most cases, some of the results suggested that the regioselectivity of the reaction is markedly influenced by the stereochemistry of the anomeric position of the substrates. The products were converted to thioglycosides (peracetate forms) by conventional means.

A Novel Route to Olefins from Vicinal Diols

A novel reagent system consisting of chlorodiphenylphosphine, imidazole, and iodine in an inert solvent converts vicinal diols to olefins.Reagents are, after completed reaction, removed by extractive procedures, which facilitates large-scale preparations.Vicinal diols consisting of either a primary and a secondary hydroxyl or two secondary hydroxyls are in this way converted to olefins in high yields.

ALLYLIC SUBSTITUTIONS IN TRI-O-BENZYL-GLYCALS, 4,6-OBENZYLIDENE-GLYCALS AND RELATED COMPOUNDS

3,4,6-Tri-O-benzyl-D-glucal and the benzyl 4,6-di-O-benzyl-2,3-dideoxy-hex-2-enopyranosides react with sodium azide in acetonitrile under boron trifluoride catalysis to yield mixtures of 3-azido-glycals and 2,3-unsaturated glycosyl azides.Similar reaction