356067-96-4

Upstream product

• 154125-72-1 (2R,4aR,8R,8aS)-8-(benzyloxy)-2-(4-methoxyphenyl)-4,4a,8,8a-tetrahydropyrano [3,2-d][1,3]dioxine 
• 791790-13-1 3-O-benzyl-4,6-O-p-methoxybenzylidene-D-glucal 
• 100-39-0 benzyl bromide 
• 312623-79-3 (4aR,8R,8aS)-2-(4-methoxyphenyl)-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-8-ol 
• 2873-29-2 D-glucal triacetate 
• 356067-93-1 3-O-benzyl-6-O-triisopropylsilyl-D-glucal 
• 13265-84-4 D-glucal 
• 187880-20-2 2,6-anhydro-5-deoxy-1,3-O-(4-methoxybenzylidene)-D-arabino-hex-5-enitol 
• 137915-37-8 1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose 
• 356067-95-3 [(2R,3S,4R)-4-Benzyloxy-3-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran-2-ylmethoxy]-triisopropyl-silane 

Downstream Products

• 356067-97-5 (2S,3S,4R)-4-Benzyloxy-3-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran-2-carboxylic acid methyl ester 
• 356068-08-1 methyl (n-pentenyl 2-O-benzoyl-3-O-benzyl-β-D-glucopyranosid)-uronate 
• 356068-02-5 (2S,3S,4R,5R,6R)-4-Benzyloxy-5-hydroxy-3-(4-methoxy-benzyloxy)-6-pent-4-enyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 356068-07-0 methyl (n-pentenyl 2-O-benzoyl-3-O-benzyl-4-O-para-methoxybenzyl-β-D-glucopyranosid)-uronate 
• 913258-73-8 (2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-(4-methoxy-benzyloxy)-3,4-dihydro-2H-pyran 
• 1279711-53-3 methyl 3,6-di-O-benzyl-4-deoxy-1R-D-galactopyranose 
• 1279711-36-2 3,6-di-O-benzyl-4-deoxy-D-glucal 
• 1279711-67-9 C₂₀H₂₂O₄ 
• 145852-76-2 3,6-di-O-benzyl-D-glucal 
• 760987-52-8 1,5-anhydro-3-O-benzyl-6-O-(3,4-dimethoxyphenyl)benzyl-2-deoxy-4-O-(4-methoxybenzyl)-D-arabinohex-1-enitol 

Relevant academic research and scientific papers

CARBOCYCLIC DERIVATIVES AND CONJUGATED DERIVATIVES THEREOF, AND THEIR USE IN VACCINES

The invention is in the field of vaccines and relates to oligomers having a selected degree of polymerization, obtained by connecting together a number of carbocyclic repeating units, and to conjugated derivatives thereof. The oligomers and conjugated derivatives thereof of the invention also have a selected degree of acetylation. The derivatives of the invention are useful for the preparation of immunogenic compositions, e.g. in the form of a vaccine.

Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides

Glycals and 4-deoxypentenosides (4-DPs), unsaturated pyranosides with similar structures and reactivity profiles, can exhibit a high degree of stereoselectivity upon epoxidation with dimethyldioxirane (DMDO). In most cases, the glycals and their corresponding 4-DP isosteres share the same facioselectivity, implying that the pyran substituents are largely responsible for the stereodirecting effect. Fully substituted dihydropyrans are subject to a "majority rule", in which the epoxidation is directed toward the face opposite to two of the three groups. Removing one of the substituents has a variable effect on the epoxidation outcome, depending on its position and also on the relative stereochemistry of the remaining two groups. Overall, we observe that the greatest loss in facioselectivity for glycals and 4-DPs is caused by removal of the C3 oxygen, followed by the C5/anomeric substituent, and least of all by the C4/C2 oxygen. DFT calculations based on polarized-π frontier molecular orbital (PPFMO) theory support a stereoelectronic role for the oxygen substituents in 4-DP facioselectivity, but less clearly so in the case of glycals. We conclude that the anomeric oxygen in 4-DPs contributes toward a stereoelectronic bias in facioselectivity whereas the C5 alkoxymethyl in glycals imparts a steric bias, which at times can compete with the stereodirecting effects from the other oxygen substituents.

Synthesis and transformations of D-glucuronic and L-iduronic acid glycals

D-Glucuronic acid glycals can be efficiently synthesized from diacetone glucose or tri-O-acetyl glycal and can be transformed into D-glucuronic acid donors and acceptors in high yields. Base catalyzed epimerization of D-glucuronic acid glycals provides access to the corresponding L-iduronic acid glycals. Both D-glucuronic and L-iduronic acid glycals were transformed into glycosylating agents for use in the synthesis of glycosaminoglycan oligosaccharides.