85549-53-7

Upstream product

• 76249-75-7 methyl (methyl 5-O-benzyl-3-deoxy-α-D-manno-oct-2-ulopyranosid)onate 
• 165875-82-1 methyl onate 
• 67-56-1 methanol 
• 29873-81-2 3-Desoxy-D-lyxo-heptulosansaeure 
• 211935-00-1 methyl (methyl 4,5,7-tri-O-benzyl-3-deoxy-α-D-lyxo-hept-2-ulopyranosid)onate 
• 221450-08-4 methyl onate 
• 221450-00-6 2,6-anyhdro-4,5,7-tri-O-(tert-butyldimethylsilyl)-1-(propane-1,3-diyl-dithioacetal)-1,3-dideoxy-D-lyxo-hept-1-enitol 
• 72605-77-7 (2R,3R,4R)-3,4-bis-benzyloxy-2-benzyloxymethyltetrahydropyran-5-one 
• 211934-98-4 2,6-anhydro-4,5,7-tri-O-benzyl-1-(propane-1,3-diyl-dithioacetal)-1,3-dideoxy-D-lyxo-hept-1-enitol 

Downstream Products

• 189238-19-5 (4aR,6R,8R,8aR)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid methyl ester 
• 186831-56-1 (2R,4R,5R,6R)-4-Benzyloxy-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 186831-58-3 (2R,4R,5R,6S)-4-Benzyloxy-5-hydroxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester 
• 186831-59-4 (2R,4R,5R,6S)-5-[(2R,3R,4R,5S)-5-((S)-1-Acetoxy-ethyl)-4-benzyloxy-3-((2S,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yloxy]-4-benzyloxy-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester 
• 210048-43-4 (2R,4R,5R,6S)-4-Benzyloxy-5-[(2S,3R,4R,5S,6S)-4,5-diacetoxy-6-methyl-3-((2S,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-methoxy-tetrahydro-pyran-2,6-dicarboxylic acid dimethyl ester 
• 178272-07-6 {(4aR,6R,8R,8aR)-6-Methoxy-2-phenyl-6-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-acetic acid methyl ester 
• 178271-93-7 (2S,3R)-2-[((4aR,6R,8R,8aR)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carbonyl)-amino]-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-butyric acid ethyl ester 
• 178272-06-5 (4aR,6R,8R,8aR)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid [(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyl]-amide 
• 189071-51-0 {(2R,4R,5R,6R)-5-Hydroxy-6-hydroxymethyl-2-methoxy-2-[(1R,2R)-2-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-tetrahydro-pyran-4-yloxy}-acetic acid methyl ester 
• 178271-92-6 (4aR,6R,8R,8aR)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid 

Relevant academic research and scientific papers

The first synthesis of the ketene dithioacetals from sugar lactones: A convenient access to 3-ulosonic acids

Isomeric 2-deoxy aldonolactones undergo Horner-Emmons reactions with 2- [bis(2,2,2-trifluoroethoxy)phosphoryl]1,3-dithiane, to give the corresponding ketene dithioacetals, which are the key intermediates in the synthesis of 3- deoxy-2-keto-aldonic acids.

Synthetic routes to methyl 3-deoxy-aldulosonic acid methyl esters and their 2-deoxy isomers based on the Horner-Emmons and Peterson reaction of sugar lactones

The two reagents: 2-trimethylsilyl- and 2-[bis(2,2,2- trifluoroethoxy)phosphoryl]-1,3-dithianes were engaged in the construction of appropriate ketene thioacetals from the isomeric 2-deoxy-hexono-1,5-lactones via Horner-Emmons or Peterson reaction. A comparison of the results shows that the second reagent is more promising, as it forms the desired ketene thioacetals as sole products. The latter were directly transformed stereoselectively into the title α ulosonates in an oxidative hydrolysis reaction, using NBS/MeOH in CH2Cl2. A construction of the methyl 2-deoxy- ulosonates involved a preceding hydrogenation of the double bond by LiBH4- TMSCl species, and subsequent hydrolysis with NBS in aqueous THF medium.

Synthesis of sialyl Lewis X mimetics and related structures using the glycosyl phosphite methodology and evaluation of E-selectin inhibition

This paper describes our recent study of glycosyl phosphites for glycosylation reactions, with particular emphasis on the investigation of protecting group and stereochemistry effects on the anomeric reactivity and stereoselectivity, and the application of this methodology to the synthesis of Lewis X (Le(x)), Lewis Y (Le(y)), glycopeptides, and sialyl Lewis X (SLe(x)) mimetics. Both α-O-fucosyl-L-threonine and α-O-fucosyl-(1R,2R)-2-aminocyclohexanol were found to be effective templates for the chemical/enzymatic synthesis of SLe(x) mimetics, and some fucopeptides prepared were 5-10 times more active than SLe(x) as inhibitors of E-selectin.

The first synthesis of 3-deoxy-D-lyxo-2-heptulosaric acid (DHA) derivatives

Synthetic route to the methyl ester of methyl glycoside of 3-deoxy-D-lyxco-heptulosaric acid (13) starting from 1-cyanogalactal 2 is described. The latter substance was prepared by direct elimination of acetic acid from 1 using 1,8-diazabicyclo[5.4.0]unde

Determination of the Anomeric Configuration in Glycosides of 3-Deoxy-2-aldulosonic Acids by Circular Dichroism and X-Ray Crystallography

Methyl (methyl 3-deoxy-D-arabino-2-heptulopyranosid)onate was obtained by acid-catalysed esterification and glycosidation of the free 2-aldulosonic acid.The molecular geometry of the glycosidic ester was determined by X-ray crystallography, and indicated both that the molecule was α-anomer and that the ring oxygen and the carboxy-group were nearly coplanar.The c.d. spectrum showed a negative n -> ?* transition band centred at 224 nm.The c.d. spectra od a number of methyl glycopyranosides derived from 6-, 7-, and 8-carbon 3-deoxy-2-aldulosonic acids demonstrated that all the compounds believed to be α-glycosides had negative maxima, and all those believed to be β-glycosides had positive maxima around 220 nm independent of their 2C5 or5C2 conformation.The only known furanoside, believed to be a β-anomer, also had a positive maximum.The chirality of the anomeric carbon atom of this class of compound can thus be conveniently established by determining the sign of the Cotton effect at 220 nm.