219703-40-9

Upstream product

• 243136-74-5 5-azido-3-oxapentyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 243136-75-6 2-{(2R,3R,4R,5S,6R)-2-[2-(2-Azido-ethoxy)-ethoxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-isoindole-1,3-dione 
• 243136-79-0 4,6-O-benzylidene-1,2,3-tris-O-acetyl-D-galactopyranoside 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 
• 129753-04-4 O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate 
• 219703-39-6 5-azido-3-oxapentyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 

Downstream Products

• 219703-46-5 2-[2-[2-(2-azido-ethoxy)-ethoxy]-6-benzyloxymethyl-5-(7,8-dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-4-(3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione 
• 219703-43-2 C₆₉H₇₄N₄O₁₉ 

Relevant academic research and scientific papers

Synthesis of a sialyl-α-(2→6)-lactosamine trisaccharide with a 5-amino-3-oxapentyl spacer group at C-1

As part of a continuing study aimed to achieve improved monoclonal antibodies against carcinoembryonic antigen (CEA) carbohydrate fragments, the synthesis of a sialyl-(2→6)-lactosamine trisaccharide with a 5-amino-3-oxapentyl spacer group at C-1(I) has been developed. Two different routes to access this target are described. For this purpose 5-azido-3-oxapentyl 6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (4) was selectively β-galactosylated in 81% yield using the crystalline 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-galactopyranosyl trichloroacetimidate as the donor, taking advantage of the bulky phthalimido group at C-2 of 4. On the other hand, galactosylation of the suitable protected acceptor 5-azido-3-oxapentyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside with the crystalline 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-galactosyl bromide renders the corresponding disaccharide in a moderate 58% yield. Despite the fact that the first strategy, unlike the second one, requires a hydrazinolysis-acetylation reaction at the disaccharide stage, it was found to be more convenient to access the disaccharide acceptor. Sialylation was performed using a thiophenyl donor under an NIS-TfOH activation procedure in acetonitrile to give a mixture of α and β trisaccharides in 49 and 16% yields, respectively. Copyright (C) 1999 Elsevier Science Ltd.

Synthesis of dimeric Lewis X antigenic determinant with azido-type spacer arm by a sequence of regioselective glycosylation steps

A new regioselective glycosylation strategy was used to develop a highly efficient synthesis of the dimeric Lewis X determinant linked to an azido type spacer arm. Regioselective galactosylation of 3,4 glucosamine diols 2 and 3 with galactose donor 4, followed by fucosylation provided two trisaccharide building blocks 9 and 10. The final condensation involved a 3b- regioselective glycosylation of the 2b,3b trisaccharide diol 11 in good yields.