155155-64-9

Basic information

• Product Name: METHYL (PHENYL 5-ACETAMIDO-4,7,8,9-TETRA-O-ACETYL-3,5-DIDEOXY-2-THIO-D-GLYCERO-D-GALACTO-2-NONULOPYRANOSID)ONATE
• Synonyms: Phenyl 4,7,8,9-tetra-O-acetyl-2-thio-N-acetyl-a-D-neuraminic acid methyl ester;Methyl (Phenyl 5-Acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate Neu5Ac[1Me,4789Ac]-SPh;Phenyl 4,7,8,9-tetra-O-acetyl-2-thio-N-acetylneuraminic acid methyl ester;Phenyl 4,7,8,9-tetra-O-acetyl-2-thio-N-acetyl-D-neuraminic acid methyl ester;N-Acetyl-2-phenylthioneuraminic Acid Methyl Ester 4,7,8,9-Tetraacetate;Methyl 5-Acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-S-phenyl-2-thio-D-glycero-D-galacto-2-nonulopyranosylonate;METHYL (PHENYL 5-ACETAMIDO-4,7,8,9-TETRA-O-ACETYL-3,5-DIDEOXY-2-THIO-D-GLYCERO-D-GALACTO-2-NONULOPYRANOSID)ONATE;METHYL 5-ACETAMIDO-4,7,8,9-TETRA-O-ACETYL-3,5-DIDEOXY-2-S-PHENYL-2-THIO-D-GLYCERO-D-GALACTO-2-NONULOPYRANOSYLONATE
• CAS NO: 155155-64-9
• Molecular Formula: C₂₆H₃₃NO₁₂S
• Molecular Weight: 583.6
• Product Categories: Biochemistry;Sialic Acids;Sugars;Thioglycosides
• Mol File: 155155-64-9.mol

Chemical Properties

• Melting Point: 183 °C
• Boiling Point: 670.995oC at 760 mmHg
• Flash Point: 359.605oC
• Appearance: /
• Density: 1.329g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: -121 ° (C=1, CHCl3)
• Storage Temp.: Freezer
• Solubility: soluble in Chloroform
• PKA: 13.79±0.70(Predicted)
• CAS DataBase Reference: METHYL (PHENYL 5-ACETAMIDO-4,7,8,9-TETRA-O-ACETYL-3,5-DIDEOXY-2-THIO-D-GLYCERO-D-GALACTO-2-NONULOPYRANOSID)ONATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL (PHENYL 5-ACETAMIDO-4,7,8,9-TETRA-O-ACETYL-3,5-DIDEOXY-2-THIO-D-GLYCERO-D-GALACTO-2-NONULOPYRANOSID)ONATE(155155-64-9)
• EPA Substance Registry System: METHYL (PHENYL 5-ACETAMIDO-4,7,8,9-TETRA-O-ACETYL-3,5-DIDEOXY-2-THIO-D-GLYCERO-D-GALACTO-2-NONULOPYRANOSID)ONATE(155155-64-9)

Safety Data

• Hazardous Substances Data: 155155-64-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
METHYL (PHENYL 5-ACETAMIDO-4,7,8,9-TETRA-O-ACETYL-3,5-DIDEOXY-2-THIO-D-GLYCERO-D-GALACTO-2-NONULOPYRANOSID)ONATE is used as a building block for the preparation of ganglioside GM3 analogs. These analogs are essential in the development of novel therapeutic agents targeting various diseases, including cancer and neurodegenerative disorders. The compound's unique structure allows for the creation of molecules with specific biological activities, making it a valuable asset in the pharmaceutical industry.
Used in Biochemical Research:
In the field of biochemistry, METHYL (PHENYL 5-ACETAMIDO-4,7,8,9-TETRA-O-ACETYL-3,5-DIDEOXY-2-THIO-D-GLYCERO-D-GALACTO-2-NONULOPYRANOSID)ONATE is employed as a key intermediate in the synthesis of complex carbohydrates and glycoconjugates. These molecules play crucial roles in cellular recognition, signal transduction, and immune responses. The compound's versatility in chemical modifications enables researchers to study the structure-function relationships of various biologically active molecules, contributing to a deeper understanding of cellular processes and the development of targeted therapies.

InChI:InChI=1/C26H33NO12S/c1-14(28)27-22-20(36-16(3)30)12-26(25(33)34-6,40-19-10-8-7-9-11-19)39-24(22)23(38-18(5)32)21(37-17(4)31)13-35-15(2)29/h7-11,20-24H,12-13H2,1-6H3,(H,27,28)/t20-,21+,22+,23+,24+,26?/m0/s1

Upstream product

• 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 
• 108-98-5 thiophenol 
• 59367-09-8 methyl acetochloroneuraminate 
• 882-33-7 diphenyldisulfane 
• 6931-68-6 methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 

Downstream Products

• 170156-72-6 2-(Trimethylsilyl)ethyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(1->6)-O-(2-acetamido-2-deoxy-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->4)-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)... 
• 187232-88-8 (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-[(2R,4aR,6R,7R,8R,8aS)-7-hydroxy-2-phenyl-6-(2-trimethylsilanyl-ethoxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 190269-56-8 5-azidopentyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-(2->3)-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 299179-55-8 methyl (phenyl 4,7,8,9-tetra-O-acetyl-5-butanoylamino-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid)onate 
• 286420-58-4 C₈₃H₁₀₆N₂O₂₇ 
• 73960-72-2 methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 
• 334934-22-4 phenyl [methyl 4,7,8,9-tetra-O-acetyl-5-(N-tert-butoxycarbonylacetamido)-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranosid]onate 

Relevant articles and documents

Synthesis of N,N-Ac,Boc laurylthio sialoside and its application to O-sialylation

The combination of the 5-N-tert-butoxycarbonyl (Boc) group of laurylthio sialoside and cyclopentyl methyl ether (CPME) as a solvent enhanced the reactivity and α-selectivity of the sialyl donor during sialylation. Selective deprotection of the N-Boc group

Synthesis of thio- and selenoglycosides by cleavage of dichalconides in the presence of zinc/zinc chloride and reaction with glycosyl bromides

A convenient odorless methodology has been devised for the preparation of 1,2-trans-thio- and selenoglycosides through zinc-mediated cleavage of disulfides and diselenides and reaction of the thiolate and selenides formed in situ with glycosyl bromides. T

Approaches to intramolecular sialylation 2. * Synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid containing an unprotected carboxy group

Various approaches to the synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid (Neu5Ac) containing an unprotected carboxy group starting from the corresponding methyl esters were comparatively studied. One-step demethylation of methyl t