127875-29-0

Upstream product

• 100-39-0 benzyl bromide 
• 389119-60-2 allyl 2,4,6-tribenzyl-3-p-methoxybenzyl-β-D-galactopyranoside 
• 125790-91-2 (2R,3R,4S,5R,6R)-2-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-ol 
• 389119-56-6 2-propenyl 3-O-(4-methoxybenzyl)-β-D-galactopyranoside 
• 2595-07-5 allyl β-D-galactopyranoside 
• 71925-95-6 allyl 4,6-O-benzylidene-β-D-galactopyranoside 
• 125790-92-3 2-propenyl 6-O-acetyl-2,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 61236-89-3 Acetic acid (3R,4S,5R,6R)-2-acetoxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yl ester 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 350254-95-4 3-O-allyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 89068-02-0 allyl 3-O-allyl-β-D-glucopyranose 
• 77388-95-5 2,4,6-tri-O-benzyl-β-D-glucopyranose 
• 1068-57-1 acetic acid hydrazide 
• 89104-67-6 1,3-di-O-acetyl-2,4,6-tri-O-benzyl-β-D-glucopyranose 

Downstream Products

• 389119-61-3 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate 
• 389119-79-3 Acetic acid (2R,3S,4S,5R,6R)-4-((2R,3R,4S,5S,6R)-4-acetoxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-allyloxy-3,5-bis-benzyloxy-tetrahydro-pyran-2-ylmethyl ester 
• 389119-80-6 2-propenyl 2,4-O-benzyl-3-O-(2,4,6-tri-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside 
• 1541178-53-3 O-(3-O-acetyl-2,4,6-tri-O-benzyl-α-D-glucopyranosyl) N-phenyltrifluoroacetimidate 
• 1541179-64-9 O-(3-O-acetyl-2,4,6-tri-O-benzyl-β-D-glucopyranosyl) N-phenyltrifluoroacetimidate 

Relevant academic research and scientific papers

Total synthesis of the: Helicobacter pylori serotype O2 O-antigen α-(1 → 2)- And α-(1 → 3)-linked oligoglucosides

Exploiting synergistic remote participation effects of acyl groups at the O3 and O6 positions was key to the complete α-selectivity during the total synthesis of the unique (1 → 2)- and (1 → 3)-linked α-oligoglucosides from the Helicobacter pylori O2 O-antigen. Acyl remote participation and solvent effects were found to counteract during α-stereoselective glucosylations for the first time. The resulting antigen is a lead for the development of a carbohydrate-conjugate vaccine.

Synthesis of helicobacter-pylorus O2 serotype O antigen oligosaccharide compound

The invention discloses discloses synthesis of a helicobacter-pylorus O2 serotype O antigen oligosaccharide compound, and belongs to the field of organic synthesis. According to the synthesis, helicobacter-pylorus O2 serotype O-antigen disaccharide to tet

Is an acyl group at O-3 in glucosyl donors able to control α-stereoselectivity of glycosylation? the role of conformational mobility and the protecting group at O-6

The stereodirecting effect of a 3-O-acetyl protecting group, which is potentially capable of the remote anchimeric participation, and other protecting groups in 2-O-benzyl glucosyl donors with flexible and rigid conformations has been investigated. To this aim, an array of N-phenyltrifluoroacetimidoyl and sulfoxide donors bearing either 3-O-acetyl or 3-O-benzyl groups in combination with 4,6-di-O-benzyl, 6-O-acyl-4-O-benzyl, or 4,6-O-benzylidene protecting groups was prepared. The conformationally flexible 3-O-acetylated glucosyl donor protected at other positions with O-benzyl groups demonstrated very low or no α-stereoselectivity upon glycosylation of primary or secondary acceptors. On the contrary, 3,6-di-O-acylated glucosyl donors proved to be highly α-stereoselective as well as the donor having a single potentially participating acetyl group at O-6. The 3,6-di-O-acylated donor was shown to be the best α-glucosylating block for the primary acceptor, whereas the best α-selectivity of glycosylation of the secondary acceptor was achieved with the 6-O-acylated donor. Glycosylation of the secondary acceptor with the conformationally constrained 3-O-acetyl-4,6-O-benzylidene-protected donor displayed under standard conditions (-35 C) even lower α-selectivity as compared to the 3-O-benzyl analogue. However, increasing the reaction temperature essentially raised the α-stereoselectivities of glycosylation with both 3-O-acetyl and 3-O-benzyl donors and made them almost equal. The stereodirecting effects of protecting groups observed for N- phenyltrifluoroacetimidoyl donors were also generally proven for sulfoxide donors.2013 Elsevier Ltd. All rights reserved.

Synthesis of a set of di- and tri-sulfated galabioses

Among cell-adhesion molecules, L-selectin recognizes sulfated sLex with relatively low affinity. Here, we aimed at artificial mimics by synthesizing a set of di- and tri-sulfated galabioses, which may surpass the affinity of sulfated sLex. As a strategy to obtain 3′,6′,6-tri-O-sulfogalabioses, regioselective reductive cleavage of 4,6- and 4′,6′-di-O-benzylidenegalabioses was employed. Two suitably protected galactose precursors were conjugated to yield α and β anomers (48 and 18%, respectively) by using a pentenyl galactoside donor and iodinium di-sym-collidine perchlorate as the catalyst. For synthesizing the 3′,6-di-O-sulfogalabiose, however, a trichloroacetimidate donor was superior (52%) to the pentenyl one (30%).

A NOVEL PROCEDURE FOR THE PREPARATION OF 1-OH SUGAR DERIVATIVES USING 2-METHOXYETHYL GLYCOSIDES

Treatment of benzyl-protected 2-methoxyethyl glycopyranosides with titanium tetrachloride followed by hydrolysis provides a new method for the preparation of the corresponding 1-OH sugar derivatives.The present method is shown to be useful for the prepara