179072-63-0

Upstream product

• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 824-94-2 p-methoxybenzyl chloride 
• 10257-28-0 D-Galactose 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 
• 25878-60-8 D-galactose pentaacetate 

Downstream Products

• 303775-37-3 phenyl 2,6-di-O-benzoyl-3-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside 
• 864270-46-2 Acetic acid (2S,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-4-(4-methoxy-benzyloxy)-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

Pentaerythritol as the core of multivalent glycolipids: Synthesis of a glycolipid with three SO3Lea ligands

(Chemical Equation Presented) A glycolipid containing three SO 3Lea ligands was synthesized with pentaerythritol as the core. The glycolipid was used to prepare glycoliposomes that showed stability similar to that of DSPC liposomes w

Directing effect by remote electron-withdrawing protecting groups at O-3 or O-4 position of donors in glucosylations and galactosylations

Glucosylations and galactosylations of various acceptors with donors possessing an electron-withdrawing benzylsulfonyl, benzoyl, or acetyl group at the O-3 or O-4 position were performed. A β-directing effect by the benzylsulfonyl group at O-3 of the glucosyl donors and by the benzylsulfonyl and acyl groups at O-4 of the glucosyl donors was observed. In contrast, acyl groups at O-3 of the glucosyl donors and acyl groups at O-3 and O-4 of the galactosyl donors exhibited an α-directing effect. The α-directing effect is partly considered to remote participation of the acyl groups, whereas the β-directing effect is somewhat attributed to the SN2-like reaction of the acceptor with the glycosyl triflate or the contact ion pair, which is stabilized by remote electron-withdrawing groups. Further evidence for the stability of the α-glycosyl triflates was determined by a low-temperature NMR study.

Polymer-supported synthesis of a branched trisaccharide of the type IA Group B Streptococcus capsular polysaccharide: 3-Iodo-4-methoxybenzyl as a new O-protecting group

The synthesis of a key branched trisaccharide (1), of the type IA Group B Streptococcus capsular polysaccharide is described. The monomethyl ether of polyethylene glycol (MeO-(CH2CH2O)(n)-H, MPEG) and dioxyxylene [p-(O)CH2-C6H4-CH2(O)-, DOX] have been used as the polymer-support/linker combination. Attempts to use the p-methoxybenzyl (PMB) protecting group under glycosylation conditions involving N-iodosuccinimide/silver trifuoromethanesulfonate promotion resulted in iodination to form the 3-iodo-4-methoxybenzyl (IPMB) derivative. Subsequently IPMB chloride was independently synthesized and used to introduce this new protecting group. The levulinoyl and the IPMB protecting groups have been used in an orthogonal manner to create 3,4-branching on a galactopyranosyl residue. Due to the enhanced acid stability of the IPMB group over the PMB group, the former group was critical to the success of the synthesis. The final trisaccharide and its intermediates were cleaved from the MPEG polymer-support by scandium(III)trifluoromethanesulfonate and acetic anhydride. (C) 2000 Elsevier Science Ltd.

Orthogonal glycosylation strategy in synthesis of extended blood group B determinant

The orthogonal glycosylation strategy was applied for the synthesis of extended blood type B determinant (2) of a novel glycolipid 1. Key features in the synthesis are 1) four monosaccharide units were synthesized as either glycosyl fluoride or thioglycoside to be engaged to the orthogonal glycosylation strategy and 2) all necessary manipulations were completed at the monosaccharide level, therefore, manipulations during the elongation of sugar chain were minimized.