211795-75-4

Upstream product

• 73-34-7 6-deoxy-L-galactose 
• 98-88-4 benzoyl chloride 
• 175981-03-0 allyl 2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-α-L-fucopyranoside 
• 175980-93-5 (2S,4aR,6S,7R,8R,8aR)-6-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 175981-04-1 allyl 3,4-di-O-acetyl-2-O-(4-methoxybenzyl)-α-L-fucopyranoside 
• 175980-95-7 Acetic acid (2S,3R,4R,5S,6S)-3-acetoxy-5-(4-methoxy-benzyloxy)-2-methyl-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester 
• 211795-72-1 Benzoic acid (2S,3R,4R,5R,6R)-5-acetylsulfanyl-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 211795-71-0 Benzoic acid (2S,3R,4S,5S,6R)-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-hydroxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 211795-73-2 Benzoic acid (2S,3R,4R,5R,6R)-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-mercapto-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 211795-70-9 Benzoic acid (2S,4aR,6S,7R,8S,8aS)-8-allyloxy-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 
• 211795-69-6 (2S,4aR,6S,7R,8R,8aS)-8-Allyloxy-6-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 211795-67-4 allyl 2-O-p-methoxybenzyl-α-L-fucopyranoside 
• 193221-61-3 Benzoic acid (2S,3R,4S,5S,6R)-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester 
• 211795-74-3 Benzoic acid (2S,3R,4R,5R,6R)-4-allyloxy-5-[(2S,3S,4R,5R,6S)-4,5-diacetoxy-3-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-ylsulfanyl]-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester 

Downstream Products

• 211795-77-6 Benzoic acid (2S,3R,4R,5S,6R)-6-acetoxymethyl-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-4-hydroxy-5-((2S,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester 
• 211795-85-6 heptyl (2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1-4)-S-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-3)]-6-O-acetyl-2-O-benzoyl-1,4-dithio-β-D-glucopyranoside 
• 211795-78-7 C₄₉H₇₀O₂₃SSi 
• 211795-83-4 C₄₃H₅₂Cl₃NO₂₃S 
• 211795-76-5 Benzoic acid (2S,3R,4R,5R,6R)-6-acetoxymethyl-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-((2S,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

Synthesis of a thio-linked Lewis A (Lea) epitope

The synthesis of heptyl (α-L-fucopyranosyl)-(1 → 4)-S-[(β-D- galactopyranosyl)-(1 → 3)]-1,4-dithio-β-D-glucopyranoside (2), as thio- linked Lewis A analogue was based on thexyldimethylsilyl 3-O-allyl-2-O- benzoyl-6-O-(4-methoxybenzyl)-4-thio-β-D-glucopyranoside (15) which was readily obtained from D-galactose. Reaction of 15 with O-3,4-di-O-acetyl-2- O-(4-methoxybenzyl)-α-L-fucopyranosyl trichloroacetimidate (8) as fucosyl donor afforded the α-(1 → 4)-thio-linked disaccharide. Replacement of the 4-methoxybenzyl groups by acetyl groups and removal of the 3a-O-allyl group afforded as 3a-O-unprotected acceptor thexyldimethylsilyl (2,3,4-tri-O- acetyl-α-L-fucopyranosyl)-(1 → 4)-S-6-O-acetyl-2-O-benzoyl-4-thio-β-D- glucopyranoside (19), which gave with 2,3,4,6-tetra-O-acetyl-α-D- galactopyranosyl trichloroacetimidate as galactosyl donor (20) the trisaccharide. Transformation into a trichloroacetimidate as glycosyl donor, glycosylation of heptylmercaptan, and then removal of the O-acyl protective groups afforded target molecule 2.