121237-39-6

Upstream product

• 1445-45-0 Trimethyl orthoacetate 
• 94926-36-0 benzyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 3616-19-1 1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 
• 67310-53-6 (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(acetoxymethyl)-6-(benzyloxy)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 18404-73-4 (2R,3R,4R,5S,6R)-2-(benzyloxy)-5-(((3aS,4R,6S,7R,7aR)-7-hydroxy-4-(hydroxymethyl)-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol 
• 59263-35-3 (3aS,4R,6S,7R,7aS)-7-(benzyloxy)-4-((benzyloxy)methyl)-2,2-dimethyl-6-(((2R,3R,4S,5R,6R)-4,5,6-tris(benzyloxy)-2-((benzyloxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-4H-[1,3]dioxolo[4,5-c]pyran 
• 70223-97-1 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl bromide 
• 18404-72-3 benzyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside 
• 171973-78-7 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-diacetylamino-6-methylsulfanyl-tetrahydro-pyran-4-yl ester 

Downstream Products

• 95580-50-0 Benzyl-O-(3,4,6-tri-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosid 
• 928824-08-2 benzyl O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-(1->3)-O-(2,6-di-O-benzyl-4-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 95580-52-2 Benzyl-O-(2-acetamido-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-(1->3)-O-(4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosid 
• 95580-54-4 Benzyl-O-(2-acetamido-2-desoxy-β-D-glucopyranosyl)-(1->3)-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosid 

Relevant academic research and scientific papers

Synthesis of lacto-N-tetraose

Human milk oligosaccharides (HMOs) are the third largest macromolecular component of breast milk and offer infants numerous health benefits, most of which stem from the development of a healthy microbiome. Characterization, quantification, and chemical de

A convenient synthesis of partially benzylated derivative of β-DGlcpNAc-(1→3)-β-D-Galp-(1→4)-β-D-Glcp-1-OBn as a versatile building block for sialyl lewis X antigens

Synthesis of the trisaccharide, benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-Dglucopyranosyl-(1→3)-2,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-benzyl-β-Dglucopyranoside (9), was achieved from building block derivatives of the component mono-

Synthesis of N-acetylglucosamine containing Lewis A and Lewis X building blocks based on N-tetrachlorophthaloyl protection - synthesis of Lewis X pentasaccharide

Phenyl 6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside (5a) and thexyldimethylsilyl 6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside (5b) gave with O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)trichloroacetimidate (8) in the presence of BF3*Et2O as catalyst exclusively lactosamine derivatives 7a and 7b, respectively, in high yields.Ensuing reaction with O-(3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl)trichloroacetimidate (9) in the presence of TMSOTf as catalyst afforded LeX trisacharide intermediates 10a,b.With fucosyl donor 9 and 5a,b as acceptors in the presence of TMSOTf as catalyst glycosylation either at the 3-O or the 4-O was observed, thus leading to mixtures of disaccharides 11a/12a and 11b/12b, respectively; their reaction with 8 furnished LeX trisaccharide intermediates 10a,b and Lea trisaccharide intermediates 14a,b.Transformation of 10b into the corresponding trichlotoacetimidate 17 and reaction with lactose acceptor 19 in the presence of Zn(OTf)2 as catalyst gave protected LeX pentasaccharide intermediate 21, which on deprotection led to unprotected LeX pentasaccharide 1. - Keywords: Glycosylation; Trichloroacetimidates; Protection; N-tetrachlorophthaloyl; Disaccharide, Trisaccharide building blocks; Lewis X; Lewis A

N,N-diacetyl-glucosamine and -galactosamine derivatives as glycosyl donors

N-Acetyl-glucosamine and N-acetyl-galactosamine were converted into the O-acetyl protected 1-methylthio-derivatives 1A,B which were then transformed into N,N-diacetyl derivatives 2A and 2B, respectively. Activation of 2A,B with DMTST afforded good glycosy