213192-07-5

Upstream product

• 213191-99-2 N-{(4aR,6R,7R,8R,8aS)-6-[2-(2-Azido-ethoxy)-ethoxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide 
• 212896-43-0 1-azido-3-oxapentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 213192-06-4 Acetic acid (2S,3R,4S,5S,6R)-2-{(2R,3S,4R,5R,6R)-5-acetylamino-6-[2-(2-azido-ethoxy)-ethoxy]-2-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-3-yloxy}-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 213192-04-2 Acetic acid (2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-[2-(2-azido-ethoxy)-ethoxy]-2-benzyloxymethyl-4-(3-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 213192-05-3 Acetic acid (2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-[2-(2-azido-ethoxy)-ethoxy]-2-benzyloxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yloxy]-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 
• 213192-03-1 N-[(2R,3R,4R,5S,6R)-2-[2-(2-Azido-ethoxy)-ethoxy]-6-benzyloxymethyl-5-hydroxy-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-acetamide 
• 213192-02-0 N-[(2R,3R,4R,5S,6R)-2-[2-(2-Azido-ethoxy)-ethoxy]-6-benzyloxymethyl-5-hydroxy-4-(3-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-acetamide 
• 213192-01-9 N-[(4aR,6R,7R,8R,8aS)-6-[2-(2-Azido-ethoxy)-ethoxy]-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide 
• 213192-00-8 N-[(4aR,6R,7R,8R,8aS)-6-[2-(2-Azido-ethoxy)-ethoxy]-8-(3-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide 
• 338971-32-7 N-{(2R,3R,4R,5S,6R)-2-[2-(2-Azido-ethoxy)-ethoxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

Synthesis of Lex and Ley oligosaccharides with azido-type spacer-arms. Comparison of 3- and 4-methoxybenzyl groups as key temporary protective groups

5-Azido-3-oxa-1-pentanol was prepared from 2-(2-chloroethoxy)ethanol and used as a spacer in the chemical synthesis of the trisaccharide β-D-Gal-(1→4)-[α-L-Fuc-(1-→3)]-GlcNAc and the tetrasaccharide α-L-Fuc-α-(1→2)-β-D-Gal-(1→4)-[α-L-Fuc- (1→3)]-GlcNAc that represent the epitopes defining the human blood groups Lex and Ley. The classical 4-methoxybenzyl group and the remarably acid-stable 3-methoxybenzyl group were compared as temporary protective groups for position 3 at the glucosamine unit to circumvent the problems associated with the simultaneous presence of allyl and azido groups. The resulting oligosaccharides were coupled to proteins with high efficiency.