156726-98-6

Basic information

• Product Name: 5-(Acetylamino)-5-deoxy-3-S-phenyl-3-thio-D-erythro-α-L-gluco-2-nonulopyranosonic Acid Methyl Ester 2,4,7,8,9-Pentaacetate
• Synonyms: 5-(Acetylamino)-5-deoxy-3-S-phenyl-3-thio-D-erythro-α-L-gluco-2-nonulopyranosonic Acid Methyl Ester 2,4,7,8,9-Pentaacetate;5-(Acetylamino)-5-deoxy-3-S-phenyl-3-thio-D-erythro-a-L-gluco-2-nonulopyranosonic acid methyl ester 2,4,7,8,9-pentaacetate
• CAS NO: 156726-98-6
• Molecular Formula: C₂₈H₃₅NO₁₄S
• Molecular Weight: 641.6408
• Product Categories: Aromatics;Carbohydrates & Derivatives;Sulfur & Selenium Compounds
• Mol File: 156726-98-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 706.596°C at 760 mmHg
• Flash Point: 381.136°C
• Appearance: /
• Density: 1.352g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.55
• CAS DataBase Reference: 5-(Acetylamino)-5-deoxy-3-S-phenyl-3-thio-D-erythro-α-L-gluco-2-nonulopyranosonic Acid Methyl Ester 2,4,7,8,9-Pentaacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(Acetylamino)-5-deoxy-3-S-phenyl-3-thio-D-erythro-α-L-gluco-2-nonulopyranosonic Acid Methyl Ester 2,4,7,8,9-Pentaacetate(156726-98-6)
• EPA Substance Registry System: 5-(Acetylamino)-5-deoxy-3-S-phenyl-3-thio-D-erythro-α-L-gluco-2-nonulopyranosonic Acid Methyl Ester 2,4,7,8,9-Pentaacetate(156726-98-6)

Safety Data

• Hazardous Substances Data: 156726-98-6(Hazardous Substances Data)

Usage

General Description

The chemical 5-(Acetylamino)-5-deoxy-3-S-phenyl-3-thio-D-erythro-α-L-gluco-2-nonulopyranosonic Acid Methyl Ester 2,4,7,8,9-Pentaacetate is a complex compound that is derived from a derivative of sialic acid, a type of sugar molecule. It contains acetyl, amino, and thio groups, as well as a phenyl group. 5-(Acetylamino)-5-deoxy-3-S-phenyl-3-thio-D-erythro-α-L-gluco-2-nonulopyranosonic Acid Methyl Ester 2,4,7,8,9-Pentaacetate is a methyl ester and is also pentaacetylated, meaning it has five acetyl groups attached. Sialic acids are important components of glycoproteins and glycolipids and play essential roles in various biological processes, including cell signaling and immune responses. The specific structure and chemical properties of this compound make it a valuable tool for studying and manipulating sialic acid-dependent processes in biological systems.

InChI:InChI=1/C28H35NO14S/c1-14(30)29-22-24(23(40-17(4)33)21(39-16(3)32)13-38-15(2)31)43-28(27(36)37-7,42-19(6)35)26(25(22)41-18(5)34)44-20-11-9-8-10-12-20/h8-12,21-26H,13H2,1-7H3,(H,29,30)/t21-,22+,23-,24?,25+,26+,28+/m1/s1

Upstream product

• 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 
• 1600-27-7 mercury(II) diacetate 
• 108-24-7 acetic anhydride 
• 108740-39-2 (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 
• 73960-72-2 methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 

Downstream Products

• 156726-99-7 Methyl onate 

Relevant articles and documents

Highly stereoselective α-sialylation. Synthesis of GM3-saccharide and a bis-sialic acid unit

The novel sialyl donor methyl [ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-thio-3-(phenylthio)-2,3,5-trideox y-D-erythro-α-L-gluco-2-nonulopyranosid]onate (6) was synthesized in six steps from N-acetylneuraminic acid in an overall yield of 47%. Donor 6 was shown to be superior to conventional sialyl donors in that the sialylation yields were higher, even with sterically hindered and unreactive sialyl acceptors, and the α/β-selectivity was virtually complete.