155835-07-7

Upstream product

• 3601-36-3 methyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside 
• 613-90-1 benzoyl cyanide 
• 3396-99-4 methyl α-D-galactopyranoside 
• 42927-28-6 methyl 6-O-benzoyl-α-D-galactopyranoside 
• 98-88-4 benzoyl chloride 
• 26927-44-6 methyl 2,6-bis-O-benzoyl-α-D-galactopyranoside 
• 1663-61-2 triethoxymethylbenzene 

Downstream Products

• 399036-37-4 methyl 3-O-acetyl-2,4,6-tri-O-benzoyl-α-D-galactopyranoside 
• 399036-11-4 C₅₃H₅₂N₄O₁₆ 
• 399036-10-3 allyl O-(3-O-acetyl-2,4,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzoyl-3-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 399036-12-5 2-azidoethyl O-(2,4,6-tri-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-6-O-benzoyl-3-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 399035-95-1 1,3-di-O-acetyl-2,4,6-tri-O-benzoyl-α-D-galactopyranose 
• 399035-96-2 3-O-acetyl-2,4,6-tri-O-benzoyl-α-D-galactopyranosyl bromide 

Relevant academic research and scientific papers

Regioselective benzoylation of sugars mediated by excessive Bu2SnO: Observation of temperature promoted migration

Regioselective benzoylation of carbohydrates using an excess of dibutyltin oxide (Bu2SnO) at increased reaction temperatures has been developed for the synthesis of several glycoside benzoates with one or two free hydroxyl groups, including gal

Study of glycosylation with N-trichloroacetyl-D-glucosamine derivatives in the syntheses of the spacer-armed pentasaccharides sialyl lacto-N-neotetraose and sialyl lacto-N-tetraose, their fragments, and analogues

The syntheses of 2-aminoethyl glycosides of the pentasaccharides Neu5Ac-α(2→3)-Gal-β(1→4)-GlcNAc-β(1→3)-Gal- β(1→4)-Glc and Neu5Ac-α(2→3)-Gal-β(1→3)-GlcNAc-β(1→3)-Gal- β(1→4)-Glc, their asialo di-, tri-, and tetrasaccharide fragments, and analogues included a systematic study of glycosylation with variously protected mono- and disaccharide donors derived from N-trichloroacetyl-D-glucosamine of galactose, lactose, and lactosamine glycosyl acceptors bearing benzoyl protection around the OH group to be glycosylated. Despite the low reactivity of these acceptors, stereospecificity and good to excellent yields were obtained with NIS-TfOH-activated thioglycoside donors of such type, or with AgOTf-activated glycosyl bromides, while other promotors, as well as a trichloroacetimidate donor, were less effective, and a β-acetate donor was inactive. In NIS-TfOH-promoted glycosylation with the thioglycosides, the use of TfOH in catalytic amount led to rapid formation of the corresponding oxazoline, but the quantity of TfOH necessary for further efficient coupling with an acceptor depended on the reactivity of the donor, varying from 0.07 equiv for a 3,6-di-O-benzylated monosaccharide derivative to 2.1 equiv for a peracetylated disaccharide one. In the glycosylation products, the N-trichloroacetyl group was easily converted into N-acetyl by alkaline hydrolysis followed by N-acetylation.

Synthesis of methyl O-α-L-rhamnopyranosyl-(12)-α-D-galactopyranosides specifically deoxygenated at position 3, 4, or 6 of the galactose residue

The title disaccharides were synthesized by condensation of 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl bromide with suitably protected, deoxygenated derivatives of methyl α-D-galactopyranoside.Deoxygenation was achieved via activation of a protected methyl α