229954-87-4

Upstream product

• 174314-11-5 2-(trimethylsilyl)ethyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 139608-36-9 phenyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 175977-99-8 phenyl 6-O-benzyl-1-thio-β-D-galactopyranoside 
• 71676-30-7 phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 174392-90-6 2-(trimethylsilyl)ethyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 107855-14-1 ethyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside 
• 229954-86-3 2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 

Downstream Products

• 229954-88-5 2-trimethylsilylethyl 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside 
• 229954-89-6 2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl-(1->3)-4-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl trichloroacetimidate 

Relevant academic research and scientific papers

Synthesis and NMR assignments of galactosylgloboside and its β-d-GalNAc-(1→4)-α-D-Gal-linked positional isomer in a conjugatable form

Two pentasaccharides suitable for conjugation, namely 3-aminopropyl glactosylgloboside and its β-D-GalNAc-(1→4)-α-D-Gal-linked positional isomer, were synthesized from 3(III),4(III)-di-O-unprotected globotrioside and the trichloroacetimidate of β-D-Gal-(1→3)-β-D-GalNPhth derivative. Glycosylation at both positions led to the formation of β-D-GalNPhth-(1→4)-α-D-Gal and β-D-GalNPhth-(1→3)-α-D-Gal-linked products in a ratio of 1:1 without selectivity. Complete NMR spectral assignments are also described. Copyright (C) 1999 Elsevier Science Ltd.

A high yielding chemical synthesis of sialyl Lewis x tetrasaccharide and Lewis x trisaccharide; examples of regio- and stereodifferentiated glycosylations

Virtually complete regioselective galactosylation of the diol acceptor p-methoxyphenyl 6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D- glucopyranoside (8) with the donor phenyl 2,3,4-tri-O-acetyl-6-O-benzyl-1- thio-β-D-galactopyranoside (11) gave the lactosamine derivative 14, which was fucosylated with the donor 15 to give the Le(x) trisaccharide glycoside 2 after deprotection. Regioselective sialylation of the partially protected Le(x) trisaccharide triol 24 with the sialyl donor 25 gave, after deprotection, the SLe(x) tetrasaccharide glycoside 1. The overall yields of 2 and 1 from the monosaccharide starting materials 8, 11, 15, and 25 were 56% and 29%, respectively. In contrast to the virtually complete regio- and stereoselective galactosylation of 8, fucosylation with the benzyl-protected donor 15 gave the corresponding 1→3- and 1→4-linked disaccharides in a ratio of 3.6:1 (highly stereo- but not regioselective glycosylation), whereas fucosylation with acetyl-protected donor 18 gave a 2.2:1 β/α-mixture of 4- O-linked disaccharides (highly regio- but not stereoselective glycosylation).