219489-03-9

Basic information

• Product Name: 4-methoxyphenyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-<2,3,4-tri-O-benzyl-α-L-fucopyranosyl>-(1->3)-(2-acetamido-2-deoxy-β-D-glucopyranoside)
• Synonyms: 4-methoxyphenyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-<2,3,4-tri-O-benzyl-α-L-fucopyranosyl>-(1->3)-(2-acetamido-2-deoxy-β-D-glucopyranoside)
• CAS NO: 219489-03-9
• Molecular Weight: 1212.35
• Mol File: 219489-03-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-methoxyphenyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-<2,3,4-tri-O-benzyl-α-L-fucopyranosyl>-(1->3)-(2-acetamido-2-deoxy-β-D-glucopyranoside)(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methoxyphenyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-<2,3,4-tri-O-benzyl-α-L-fucopyranosyl>-(1->3)-(2-acetamido-2-deoxy-β-D-glucopyranoside)(219489-03-9)
• EPA Substance Registry System: 4-methoxyphenyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-<2,3,4-tri-O-benzyl-α-L-fucopyranosyl>-(1->3)-(2-acetamido-2-deoxy-β-D-glucopyranoside)(219489-03-9)

Safety Data

• Hazardous Substances Data: 219489-03-9(Hazardous Substances Data)

Upstream product

• 219488-95-6 4-methoxyphenyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-(6-O-benzyl-2-deoxy-2-(tetrachlorophthalimido)-β-D-glucopyranoside) 
• 219488-90-1 4-methoxyphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-(tetrachlorophthalimido)-β-D-glucopyranoside 
• 219488-93-4 p-methoxyphenyl 6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside 
• 219488-92-3 4-methoxyphenyl 4,6-O-benzylidene-2-deoxy-2-(tetrachlorophthalimido)-β-D-glucopyranoside 
• 219488-91-2 4-methoxyphenyl 2-deoxy-2-(tetrachlorophthalimido)-β-D-glucopyranoside 
• 139608-36-9 phenyl 2,3,4-tri-O-acetyl-6-O-benzyl-1-thio-β-D-galactopyranoside 
• 183388-14-9 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(tetrachlorophthalimido)-β-D-glucopyranose 
• 175977-99-8 phenyl 6-O-benzyl-1-thio-β-D-galactopyranoside 
• 5432-46-2 1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride 
• 71676-30-7 phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 16758-34-2 1-thiophenyl-β-D-galactopyranoside 
• 116514-50-2 ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside 
• 219489-02-8 4-methoxyphenyl (2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-(2-acetamido-6-O-benzyl-2-deoxy-β-D-glucopyranoside) 

Downstream Products

• 219489-06-2 4-methoxyphenyl (6-O-benzyl-β-D-galactopyranosyl)-(1->4)-<2,3,4-tri-O-benzyl-α-L-fucopyranosyl>-(1->3)-(2-acetamido-2-deoxy-β-D-glucopyranoside) 

Relevant articles and documents

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).