175981-04-1

Basic information

• Product Name: allyl 3,4-di-O-acetyl-2-O-(4-methoxybenzyl)-α-L-fucopyranoside
• Synonyms: allyl 3,4-di-O-acetyl-2-O-(4-methoxybenzyl)-α-L-fucopyranoside
• CAS NO: 175981-04-1
• Molecular Weight: 408.449
• Mol File: 175981-04-1.mol

Chemical Properties

• CAS DataBase Reference: allyl 3,4-di-O-acetyl-2-O-(4-methoxybenzyl)-α-L-fucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: allyl 3,4-di-O-acetyl-2-O-(4-methoxybenzyl)-α-L-fucopyranoside(175981-04-1)
• EPA Substance Registry System: allyl 3,4-di-O-acetyl-2-O-(4-methoxybenzyl)-α-L-fucopyranoside(175981-04-1)

Safety Data

• Hazardous Substances Data: 175981-04-1(Hazardous Substances Data)

Upstream product

• 175981-03-0 allyl 2-O-(p-methoxybenzyl)-3,4-O-isopropylidene-α-L-fucopyranoside 
• 108182-34-9 allyl 3,4-di-O-isopropylidene-α-L-fucopyranoside 
• 73-34-7 6-deoxy-L-galactose 
• 108-24-7 acetic anhydride 
• 211795-67-4 allyl 2-O-p-methoxybenzyl-α-L-fucopyranoside 

Downstream Products

• 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 
• 211795-75-4 Benzoic acid (2S,3R,4R,5R,6R)-4-allyloxy-5-((2S,3S,4S,5R,6S)-4,5-diacetoxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-ylsulfanyl)-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-hydroxymethyl-tetrahydro-pyran-3-yl ester 
• 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 
• 211795-76-5 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 
• 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 
• 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 
• 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 

Relevant articles and documents

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.

Synthesis of a thio-linked analogue of sialyl Lewis X

Thiolinked sialyl Lewis X analogue 2 was obtained from neuraminic acid, D-galactose, and L-fucose. Galactose was transformed into 3-thiogalactose building block 6 and also into the required 3,4-dithioglucose moiety. Thioglycoside bond formation was performed via base-promoted S-glycosylation [Neu5Acα(2-3S)Gal and Galβ(1-4S)Glc linkages] and via acid catalyzed S-glycosylation [Fucα(1-3S)Glc and Glcβ-(1-1S)heptyl linkages].