253683-41-9

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 145852-76-2 3,6-di-O-benzyl-D-glucal 
• 69739-34-0 t-butyldimethylsiyl triflate 

Downstream Products

• 253683-26-0 dibutyl 4-O-tert-butyldimethylsilyl-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside phosphate 
• 385421-81-8 n-pentenyl 4,6-di-O-benzyl-3-O-levulinyl-2-O-pivaloyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside 
• 385421-82-9 n-pentenyl 4,6-di-O-benzyl-2-O-pivaloyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside 
• 385422-18-4 n-pentenyl 4-O-tert-butyldimethylsilyl-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside 
• 385421-79-4 4-pentenyl 3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside 
• 373606-36-1 3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside 
• 373606-35-0 dibutyl 3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside phosphate 
• 511511-39-0 Acetic acid (2S,3R,4S,5R,6S)-5-acetoxy-6-acetoxymethyl-2-[(2R,3R,4R,5S,6R)-6-(2-azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-yloxy]-4-methoxy-tetrahydro-pyran-3-yl ester 
• 511511-40-3 (2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5S,6R)-6-(2-Azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid benzyl ester 
• 511511-34-5 [(2R,3R,4R,5S,6R)-6-(2-Azido-ethyl)-4-benzyloxy-2-benzyloxymethyl-5-methoxy-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane 
• 511511-33-4 2-[(2R,3S,4R,5R,6R)-4-Benzyloxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-tetrahydro-pyran-2-yl]-ethanol 
• 511511-31-2 (2R,3S,4R,5R,6R)-4-Benzyloxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-2-ethynyl-tetrahydro-pyran-3-ol 
• 511511-32-3 ((2R,3R,4R,5S,6R)-4-Benzyloxy-2-benzyloxymethyl-6-ethynyl-5-methoxy-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane 

Relevant academic research and scientific papers

Glycal glycosylation and 2-nitroglycal concatenation, a powerful combination for mucin core structure synthesis

(Chemical Equation Presented) A 3,4-O-unprotected galactal derivative having bulky 6-O-TIPS protection (compound 2) could be regioselectively 3-O-glycosylated with O-(galactopyranosyl) trichloroacetimidates; depending on the protecting group pattern stere

Probing the heparin - Antithrombin III interaction using synthetic pentasaccharides bearing positively charged groups

Four heparin pentasaccharides bearing either one (i.e. 3b and 4b) or two (i.e. 3c and 4c) positively charged amino groups at the reducing end have been synthesized and evaluated for their antithrombin III mediated anti-Xa activity. The positively charged groups were introduced to interact specifically with the negatively charged amino acid residues Glu113 and Asp117 of antithrombin III, which are located in the heparin binding site in close proximity to the reducing end of the saccharide. It turned out that the target compounds 3b,c and 4b,c exhibited relatively low anti-Xa activities, indicating unfavorable interactions between the new pentasaccharides and antithrombin III rather than the anticipated enhancement of association. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Linear synthesis of a protected H-type II pentasaccharide using glycosyl phosphate building blocks

A linear synthesis of a fully protected H-type II blood group determinant pentasaccharide utilizing glycosyl phosphate and glycosyl trichloroacetimidate building blocks is reported. Envisioning an automated solid-phase synthesis of blood group determinants, the utility of glycosyl phosphates in the stepwise construction of complex oligosaccharides, such as the H-type II antigen, is demonstrated. Installation of the central glucosamine building block required the screening of a variety of nitrogen protecting groups to ensure good glucosamine donor reactivity and protecting group compatibility. The challenge to differentiate C2 of the terminal galactose in the presence of other hydroxyl and amine protecting groups prompted us to introduce the 2-(azidomethyl)benzoyl group as a novel mode of protection for carbohydrate synthesis. The compatibility of this group with traditionally employed protecting groups was examined, as well as its use as a C2 stereodirecting group in glycosylations. The application of the 2-(azidomethyl)benzoyl group along with a systematic evaluation of glycosyl donors allowed for the completion of the pentasaccharide and provides a synthetic strategy that is expected to be generally amenable to the solid support synthesis of blood group determinants.