81928-96-3

Upstream product

• 108-24-7 acetic anhydride 
• 100-39-0 benzyl bromide 
• 21193-75-9 D-galactal 
• 81928-98-5 4,6-di-O-benzyl-D-galactal 

Downstream Products

• 1327259-77-7 cyclohexyl 2-deoxy-3-O-acetyl-4,6-di-O-benzyl-α-D-lyxo-hexopyranoside 
• 1327260-15-0 C₅₂H₆₆O₁₅ 
• 1327260-14-9 2-deoxy-3,4,6-tri-O-benzyl-α-D-lyxo-hexopyranosyl-(1->6)-3-hyroxy-1,2,4-tri-O-methyl-α-D-glucopyranose 
• 471930-56-0 dibutyl 3-acetyl-4,6-dibenzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranosyl phosphate 
• 471930-67-3 dimethylthexylsilyl 3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside 
• 471930-69-5 3-acetyl-4,6-dibenzyl-2-deoxy-2-trichloroacetamido-α-D-galactopyranosyl trichloroacetimidate 
• 471930-68-4 Acetic acid (2R,3R,4R,5R,6R)-3-benzyloxy-2-benzyloxymethyl-6-hydroxy-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester 
• 471930-66-2 dimethylthexylsilyl 3-acetyl-2-azido-4,6-dibenzyl-2-deoxy-β-D-galactopyranoside 

Relevant academic research and scientific papers

Study of the stereoselectivity of 2-azido-2-deoxygalactosyl donors: Remote protecting group effects and temperature dependency

The stereoselectivity of glycosylation reactions is affected by many factors. Synthesis of 1,2-cis glycosidic linkages (such as α linkages in glucose and galactose like monosaccharides) is challenging due to lack of control of the stereoselectivity. Our s

Linear synthesis of the tumor-associated carbohydrate antigens Globo-H, Ssea-3, and Gb3

The tumor-associated carbohydrate antigens Globo-H, SSEA-3, and Gb3 were synthesized in a linear fashion using glycosyl phosphate monosaccharide building blocks. All of the building blocks were prepared from readily available common precursors. The difficult α-(1→-4-cis)-galactosidic linkage was installed using a galactosyl phosphate donor with high selectivity. Introduction of the β-galactosamine unit required the screening a variety of amine protecting groups to ensure good donor reactivity and protecting group compatibility. An N-trichloroacetyl-protected galactosamine donor performed best for the installation of the β-glycosidic linkage. Conversion of the trichloroacetyl group to the N-acetyl group was achieved under mild conditions, fully compatible with the presence of multiple glycosidic bonds. This synthetic strategy is expected to be amenable to the synthesis of the globo-series of tumor antigens on solid-support.

Glycosyl imidates, 74: Synthesis of ganglioside GM1 via a GM3 intermediate

The synthesis of GM1 (1) via GM3 intermediate 7 was based on lactose building-block 5, sialyl donors 6, and a Galβ(1-3)-GalN3 donor 13α. Reaction of donor 13α with acceptor 7 in the presence of TMSOTf as catalyst afforded GM1 pentasaccharide 30. Azido group reduction, N-acetylation, hydrogenolytic O-debenzylation, and O-acetylation furnished O-acyl-protected GM1 pentasaccharide 34. Chemoselective 1a-O-deacetylation and generation of O-(pentaosyl)trichloroacetimidate 36 provided the required glycosyl donor for the application to azidosphingosine glycosylation procedure affording GM1 (1). VCH Verlagsgesellschaft mbH, 1996.

THE ALKYLATION AND ACYLATION OF GLYCALS VIA AN INITIALIZING ELECTROCHEMICAL STEP

The method of electrochemically induced formation of ether and ester derivatives of saturated mono- and disaccharides was applied to 1,2-unsaturated monosaccharides (D-glycals).The influence of the supporting electrolyte on the product distribution was investigated by variation of the cation.To provide data for comparison, alkylation was also carried out chemically in the presence of different bases, e.g.LiH and NaH.