175981-03-0

Basic information

• Product Name: allyl 2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-α-L-fucopyranoside
• Synonyms: allyl 2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-α-L-fucopyranoside
• CAS NO: 175981-03-0
• Molecular Weight: 364.439
• Mol File: 175981-03-0.mol

Chemical Properties

• CAS DataBase Reference: allyl 2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-α-L-fucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: allyl 2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-α-L-fucopyranoside(175981-03-0)
• EPA Substance Registry System: allyl 2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-α-L-fucopyranoside(175981-03-0)

Safety Data

• Hazardous Substances Data: 175981-03-0(Hazardous Substances Data)

Upstream product

• 108182-34-9 allyl 3,4-di-O-isopropylidene-α-L-fucopyranoside 
• 824-94-2 p-methoxybenzyl chloride 
• 2746-25-0 p-Methoxybenzyl bromide 
• 73-34-7 6-deoxy-L-galactose 
• 41308-77-4 allyl α-L-fucopyranoside 

Downstream Products

• 175981-04-1 allyl 3,4-di-O-acetyl-2-O-(4-methoxybenzyl)-α-L-fucopyranoside 
• 211795-67-4 allyl 2-O-p-methoxybenzyl-α-L-fucopyranoside 
• 175981-11-0 C₃₆H₃₈Cl₃NO₁₄S₂ 
• 175981-10-9 Thexyldimethylsilyl 4-S-acetyl-2,6-di-O-benzoyl-3-S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-3,4-dithio-β-D-glucopyranoside 
• 175981-07-4 Thexyldimethylsilyl 2-O-benzoyl-4,6-O-benzylidene-3-S-(3,4-di-O-acetyl-2-p-methoxybenzyl-α-L-fucopyranosyl)-3-thio-β-D-galactopyranoside 
• 175981-12-1 Heptyl 4-S-acetyl-2,6-di-O-benzoyl-3-thio-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-1,3,4-trithio-β-D-glucopyranoside 
• 175980-99-1 Heptyl S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-2,6-di-O-benzoyl-4-thio-β-D-glucopyranoside 
• 175980-97-9 Thexyldimethylsilyl 2,6-di-O-benzoyl-3-S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-3-thio-β-D-galactopyranoside 
• 175981-08-5 Thexyldimethylsilyl 2-O-benzoyl-4,6-O-benzylidene-3-S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-3-thio-β-D-galactopyranoside 
• 175981-05-2 Acetic acid (2S,3R,4R,5S,6R)-3-acetoxy-6-hydroxy-5-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-4-yl ester 
• 211795-83-4 C₄₃H₅₂Cl₃NO₂₃S 
• 211795-78-7 C₄₉H₇₀O₂₃SSi 
• 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 
• 211795-74-3 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 

Relevant articles and documents

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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.

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