870001-83-5

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 870001-82-4 Acetic acid (2R,3S,4R,5R,6S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(4-methoxy-benzyloxy)-6-p-tolylsulfanyl-tetrahydro-pyran-4-yl ester 
• 870001-81-3 Acetic acid (2S,3R,4R,5S,6R)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-2-p-tolylsulfanyl-tetrahydro-pyran-4-yl ester 

Downstream Products

• 870001-62-0 p-tolyl 2-azido-6-O-(tert-butyldiphenylsilyl)-1,2-deoxy-3-levulinoyl-4-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranoside 
• 870001-87-9 (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-hydroxymethyl-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 870001-91-5 (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-amino-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxy]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 870001-67-5 (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-4-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid 
• 870001-86-8 (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-4-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 870001-88-0 (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxy-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 870001-89-1 (2S,3S,4S,5R,6S)-5-Acetoxy-3-[(2R,3R,4R,5S,6R)-3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yloxy]-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 870001-90-4 3-[3-azido-6-(tert-butyl-diphenyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-4-(4-oxo-pentanoyloxy)-tetrahydro-pyran-2-yloxy]-5-hydroxy-6-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 870001-64-2 methyl (methyl 4-O-[2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-4-O-(p-methoxybenzyl)-α-D-glucopyranosyl]-2-O-acetyl-3-O-[2-(trimethylsilyl)ethoxymethyl]-α-D-glucopyranosyluronate) 

Relevant academic research and scientific papers

Synthesis and reactivity of 4'-deoxypentenosyl disaccharides

4-Deoxypentenosides (4-DPs) are versatile synthons for rare or higher-order pyranosides, and they provide an entry for structural diversification at the C5 position. Previous studies have shown that 4-DPs undergo stereocontrolled DMDO oxidation; subsequent epoxide ring-openings with various nucleophiles can proceed with both anti or syn selectivity. Here, we report the synthesis of α- and β-linked 4'-deoxypentenosyl (4'-DP) disaccharides, and we investigate their post-glycosylational C5' additions using the DMDO oxidation/ring-opening sequence. The α-linked 4'-DP disaccharides were synthesized by coupling thiophenyl 4-DP donors with glycosyl acceptors using BSP/Tf2O activation, whereas β-linked 4'-DP disaccharides were generated by the decarboxylative elimination of glucuronyl disaccharides under microwave conditions. Both α- and β-linked 4'-DP disaccharides could be epoxidized with high stereoselectivity using DMDO. In some cases, the α-epoxypentenosides could be successfully converted into terminal l-iduronic acids via the syn addition of 2-furylzinc bromide. These studies support a novel approach to oligosaccharide synthesis, in which the stereochemical configuration of the terminal 4'-DP unit is established at a post-glycosylative stage.

Orthogonal sulfation strategy for synthetic heparan sulfate ligands

(Chemical Equation Presented) An orthogonal sulfation strategy involving six different protecting groups has been developed for generating sulfated carbohydrate libraries based on heparan. Chemoselective cleavage conditions (optimized for a heparan disacc