176106-81-3

Basic information

• Product Name: Lewis X Trisaccharide, Methyl Glycoside
• Synonyms: Methyl 2-Acetamido-2-deoxy-3-O-(a-L-fucopyranosyl)-4-O-(b-D- galactopyranosyl)-b-D-glucopyranoside, Gal1-b-4[Fuc1-a-3] GlcNAc1-b-O-Me;LewisXtrisaccharidemethylglucoside;Methyl 2-Acetamido-2-deoxy-3-O-(α-L-fucopyranosyl)-4-O-(b-D- galactopyranosyl)-β-D-glucopyranoside, Gal1-β-4[Fuc1-α-3] GlcNAc1-β-O-Me;Gal1-b-4[Fuc1-α-3] GlcNAc1-b-O-Me;Methyl 2-AcetaMido-2-deoxy-3-O-(α-L-fucopyranosyl)-4-O-(b-D- galactopyranosyl)-b-D-glucopyranoside
• CAS NO: 176106-81-3
• Molecular Formula: C21H37NO15
• Molecular Weight: 543.515
• Product Categories: Oligosaccharide Compounds;Oligosaccharides
• Mol File: 176106-81-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 174-176°C
• Boiling Point: 853.8°C at 760 mmHg
• Flash Point: 470.2°C
• Appearance: /
• Density: 1.57g/cm³
• Vapor Pressure: 6.14E-34mmHg at 25°C
• Refractive Index: 1.607
• Storage Temp.: -20°C Freezer
• CAS DataBase Reference: Lewis X Trisaccharide, Methyl Glycoside(CAS DataBase Reference)
• NIST Chemistry Reference: Lewis X Trisaccharide, Methyl Glycoside(176106-81-3)
• EPA Substance Registry System: Lewis X Trisaccharide, Methyl Glycoside(176106-81-3)

Safety Data

• Hazardous Substances Data: 176106-81-3(Hazardous Substances Data)

Usage

Chemical Properties

Off-White to Pale Yellow Solid

Uses

Lewis X and related compounds bind to the selectins and act as anti-inflammatory agents.

InChI:InChI=1/C21H37NO15/c1-6-11(26)13(28)15(30)20(33-6)37-18-10(22-7(2)25)19(32-3)35-9(5-24)17(18)36-21-16(31)14(29)12(27)8(4-23)34-21/h6,8-21,23-24,26-31H,4-5H2,1-3H3,(H,22,25)

Upstream product

• 313342-35-7 methyl O-(2,3,4-tri-O-acetyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)-[(3,4-di-O-acetyl-2-O-benzyl-α-L-fucopyranosyl)-(1->3)]-2-acetamido-2-deoxy-α-D-glucopyranoside 
• 6619-02-9 methyl N-acetyl-2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 481052-23-7 methyl O-(3,4-di-O-acetyl-2-O-benyzl-α-L-fucopyranosyl)-(1->3)-2-acetamido-2-deoxy-6-O-(2,2,2-trichloroethoxycarbonyl)-α-D-glucopyranoside 
• 481052-22-6 methyl O-(3,4-di-O-acetyl-2-O-benyzl-α-L-fucopyranosyl)-(1->3)-2-acetamido-2-deoxy-α-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 1045775-20-9 C₄₈H₅₅NO₂₁ 
• 183875-22-1 phenyl 2-azido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-α/β-D-glucopyranoside 
• 183875-25-4 phenyl 2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside 
• 183875-02-7 phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside 
• 196397-53-2 phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-fucopyranoside 
• 202462-37-1 phenyl 2-azido-2-deoxy-1-thio-α/β-D-glucopyranoside 
• 261374-57-6 phenyl 1-thio-α-L-fucopyranoside 
• 183875-20-9 Acetic acid (2R,3S,4R,5R,6R)-5-azido-6-phenylsulfanyl-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester 
• 183875-13-0 2,2-Dimethyl-propionic acid (2R,3R,4S,5S,6R)-2-((2R,4aR,6R,7R,8R,8aS)-7-azido-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl ester 

Relevant articles and documents

Application and limitations of the methyl imidate protection strategy of N-acetylglucosamine for glycosylations at O-4: synthesis of Lewis A and Lewis X trisaccharide analogues

We describe here the synthesis of the allyl Lea trisaccharide antigen as well as that of an analogue of the Lex trisaccharide antigen, in which the galactose residue has been replaced by a glucose unit. Although successful fucosylations at O-4 of N-acetylglucosamine acceptors have been reported using perbenzylated thioethyl fucosyl donors under MeOTf activation, such conditions led in our case to the conversion of our acceptor to the corresponding alkyl imidates. Indeed, in this synthesis of the Lea analogue, we demonstrate that the temporary protection of the N-acetyl group as a methyl imidate is advantageous to fucosylate at O-4. In contrast, we report here that glucosylation at O-4 of an N-acetylglucosamine monosaccharide acceptor using the α-trichloroacetimidate of peracetylated glucopyranose as a donor proceeded in better yields under activation with excess BF3·OEt2 than that of the corresponding methyl imidate. Therefore, we conclude that activation of thioglycoside donors by MeOTf to glycosylate at O-4 of a glucosamine acceptor is best accomplished following the temporary protection of the N-acetyl group as a methyl imidate, especially when the donors are highly reactive and prone to degradation. In contrast, if donor and acceptor can withstand multiple equivalents of BF3·OEt2, glycosylations at O-4 of a glucosamine acceptor with a trichloroacetimidate donor does not benefit from the temporary protection of the N-acetyl group as a methyl imidate.

Carbohydrate-carbohydrate recognition between Lewis X blood group antigens, mediated by calcium ions

Bivalent Lewis X (LeX) oligosaccharides were synthesised in order to study the conformational details of carbohydrate clusters by NMR spectroscopy. To this end, two Lex trisaccharide moieties (1) were covalently linked through the 6-hydroxy group or through the anomeric oxygen of GlcNAc to yield dimers 2 and 3, respectively. The two Lex halves of the model saccharide 2 exhibited cooperativity in calcium binding. Three different lactosides served as control compounds for NMR titration with calcium chloride. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Generalizing glycosylation: Synthesis of the blood group antigens Lea, Leb, and Le(x) using a standard set of reaction conditions

Because there are no general reaction conditions for any glycosylation method, biologically interesting oligosaccharides can only be made in a small number of laboratories in the world. To make carbohydrate synthesis accessible to nonspecialists, it is critical to have glycosylation methods that will work in a wide range of cases under a single set of conditions. The Lewis blood group antigens have attracted the attention of numerous synthetic carbohydrate groups because of their structural complexity. Although they have been synthesized many times, they have never been made using a single glycosylation method under one set of reaction conditions. In this paper, we show that the sulfoxide glycosylation method can be used to form all of the glycosidic linkages in the Lewis blood group antigens Lea (1), Leb (2), and Le(x) (3) stereoselectively under a uniform set of reaction conditions. This work highlights the flexibility of the sulfoxide method and demonstrates its utility for constructing families of related oligosaccharides.