20298-34-4

Basic information

• Product Name: methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-acetamido-α-D-glycero-D-galacto-2-nonulopyranosonate
• CAS NO: 20298-34-4
• Molecular Weight: 491.449
• Mol File: 20298-34-4.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-acetamido-α-D-glycero-D-galacto-2-nonulopyranosonate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-acetamido-α-D-glycero-D-galacto-2-nonulopyranosonate(20298-34-4)
• EPA Substance Registry System: methyl 4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-acetamido-α-D-glycero-D-galacto-2-nonulopyranosonate(20298-34-4)

Safety Data

• Hazardous Substances Data: 20298-34-4(Hazardous Substances Data)

Upstream product

• 155155-64-9 (4S,5R,6R)-4-Acetoxy-5-acetylamino-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 57-88-5 cholesterol 
• 91041-78-0 methyl N-acetyl-4,7,8,9-tetra-O-acetyl-2-fluoro-α-D-neuraminate 
• 91041-78-0 methyl N-acetyl-4,7,8,9-tetra-O-acetyl-2-fluoro-β-D-neuraminate 
• 24850-33-7 allyltributylstanane 
• 20298-35-5 N-acetylneuraminic acid methyl ester 
• 108-24-7 acetic anhydride 
• 6813-81-6 N-acetyl neuraminic acid 

Downstream Products

• 170298-66-5 methyl <5-acetamido-4,7,8,9-tetra-O-acetyl-2-(phenoxycarbonyloxy)-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosyl>onate 
• 73960-72-2 methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 
• 874904-90-2 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 2-(N-phenyl)trifluoroacetimidate 
• 1374853-99-2 C₃₂H₄₅NO₁₃ 
• 1374838-89-7 C₃₃H₄₇NO₁₃ 
• 1374853-98-1 sodium (3-methyl-5-phenylpentanyl-5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranoside)onate 
• 345209-46-3 (4S,5R,6R)-4-Acetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 96520-22-8 benzyl O--(2->3)-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 133411-35-5 ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosylonate)-(2->3)-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside 
• 133411-36-6 ethyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-S-phenyl-3-thio-D-erythro-β-L-gluco-2-nonulopyranosylonate)-(2->3)-2,4-di-O-acetyl-6-O-pivaloyl-β-D-galactopyranosyl-(1->4)-3-O-acetyl-2,6-di-O-pivaloyl-1-thio-β-D-glucopyranoside 
• 120104-58-7 (2S,3S,4R,5S,6R)-4-Acetoxy-5-acetylamino-2-chloro-3-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 90124-30-4 methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 109681-25-6 methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 144240-36-8 methyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate 

Relevant articles and documents

Chemical and enzymatic synthesis of high-affinity selectin ligands

Analogs of sialyl Lewis(X) have been synthesized chemically using donors of modified sialic acids. The sialic acids were obtained enzymatically by an aldolase reaction. The sLe(x) tetrasaccharides modified at C-2 of the GlcNAc moiety and at C-5 of the sialic acid residue were tested as inhibitors for E- and P-selectins. Up to 12-fold higher inhibitory potency was found for the lyso-derivative of sLeX compared to the parent compound.

An efficient synthesis of C3 C-alkylated Neu5Ac2en derivatives

C3-modified Neu5Ac2en derivatives can be used to study the flexible 150-loop region of influenza virus sialidases and also provide a new template for the development of next-generation sialidase inhibitors. This Letter describes an efficient synthetic route towards the large scale synthesis of C3 C-alkylated Neu5Ac2en derivatives. The key intermediate, a 3-eq-allyl-Neu5Ac derivative, is formed by stereoselective addition of the allyl group in an equatorial configuration at C3, regardless of the stereochemistry of the bromohydrin precursor.

Highly efficient α-sialylation by virtue of fixed dipole effects of N-phthalyl group: Application to continuous flow synthesis of α(2-3)-and α(2-6)-Neu5Ac-Gal motifs by microreactor

Highly α-selective sialylation of sialic acid N- phenyltrifluoroacetimidate with various galactose and lactose acceptors has been achieved by introducing the C-5 N-phthalyl group on the donor. The "fixed dipole effect" of the N-phthalyl group was proposed to explain the high reactivity and α-selectivity. The microfluidic system was applied to the present α-sialylation, which is amenable to large-scale synthesis. The N-phthalyl group was removed by treatment with methylhydrazine acetate, for which protocol can be readily applied to the synthesis of a variety of sialic acid-containing oligosaccharides. (Chemical Equation Presented). Copyright Taylor & Francis Group, LLC.