139526-08-2

Upstream product

• 98-88-4 benzoyl chloride 
• 155-30-6 methyl 1-thio-β-D-galactopyranoside 
• 55722-48-0 methyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 61198-88-7 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide 
• 917-64-6 methyl magnesium iodide 
• 158419-90-0 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl thiocyanate 

Downstream Products

• 139526-09-3 allyl O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->3)-2-azido-4,6-di-O-benzyl-2-deoxy-β-D-galactopyranoside 
• 390400-38-1 C₅₇H₆₁NO₁₅ 
• 847159-01-7 methyl 2-O-acetyl-4-O-(4-methoxybenzyl)-3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-α-L-rhamnopyranoside 
• 139525-90-9 allyl O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside 
• 139526-13-9 O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-D-galactopyranosyl fluoride 
• 139526-12-8 O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-D-galactopyranose 
• 139526-11-7 allyl O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->3)-2-azido-4,6-di-O-benzyl-2-deoxy-β-D-galactopyranoside 
• 139526-10-6 allyl O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->3)-2-azido-4,6-di-O-benzyl-2-deoxy-β-D-galactopyranoside 
• 143571-99-7 (2R,3R,4R,5S)-5-Acetoxy-2-benzyloxymethyl-3-((2R,3R,4S,5S,6R)-3,4,5-tris-benzoyloxy-6-benzoyloxymethyl-tetrahydro-pyran-2-yloxy)-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-piperidine-1-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Reaction of sugar thiocyanates with Grignard reagents. New synthesis of thioglycosides

Glycosyl thiocyanates having hydroxyl groups protected with acetyl or benzoyl groups react readily at -40°C with Grignard reagents to afford the corresponding alkyl or aryl thioglycosides in good yields. Monosaccharide derivatives having the SCN grouping at other positions form under similar conditions thioethers. Axial thiocyanates do not react. Elevated temperatures induce side reactions leading to mercaptans.

Studies Directed toward the Synthesis of Polysialogangliosides: The Regio- and Stereocontrolled Synthesis of Rationally Designed Fragments of the Tetrasialoganglioside GQ1b

The synthesis of suitably protected fragments of the tetrasialoganglioside GQ1b (I), i. e., 1 (αNeuAc2->8αNeuAc2->3βGal1->4Glc), 2 (αNeuAc2->8αNeuAc2->3Gal), 3 (GalNAc), 4 (αNeuAc2->8NeuAc), 5 (βGal1->3GalNAc), and 42 3βGalNAc1->4(αNeuAc2->3)βGal->4Glc>, is described.All are rationally designed so that the protecting groups can be regioselectively introduced and removed, as needed, before or after the stereoselective coupling of an appropriate pair of fragments.The syntheses of 1, 2, and 4 all feature stereoselective glycosylations by glycosyl donors that bear a C-3 thiophenoxy stereocontrolling auxiliary.Compound 3 was prepared from the D-glucosamine derivative 17 by way of a novel intramolecular nucleophilic displacement with inversion of configuration.Furthermore, model glycosylations of 4-hydroxygalactose derivatives, in which the thioglycoside 3 and the fluoride 40 served as glycosyl donors, were performed.The reaction of 3 with the glycosyl acceptor 30 gave the disaccharide 31 (GalNAcβ1->4Gal), whereas that of 40 with 41 afforded the pentasaccharide 42.