156726-99-7

Basic information

• Product Name: Methyl onate
• Synonyms: Methyl onate
• CAS NO: 156726-99-7
• Molecular Weight: 643.733
• Mol File: 156726-99-7.mol

Chemical Properties

• CAS DataBase Reference: Methyl onate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl onate(156726-99-7)
• EPA Substance Registry System: Methyl onate(156726-99-7)

Safety Data

• Hazardous Substances Data: 156726-99-7(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 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 
• 75-08-1 ethanethiol 
• 156726-98-6 Methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-3-(phenylthio)-D-erythro-β-L-gluco-2-nonulopyranosonate 
• 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

• 221524-10-3 methyl onate 
• 221524-15-8 2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-5-N,N-diacetylamino-3,5-dideoxy-3-phenylthio-D-erythro-β-L-gluco-non-2-ulopyranosylonate)-(2->3)-4-O-acetyl-2-azido-6-O-benzoyl-2-deoxy-β-D-galactopyranoside 
• 221524-14-7 2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-5-N,N-diacetylamino-3,5-dideoxy-3-phenylthio-D-erythro-β-L-gluco-non-2-ulopyranosylonate)-(2->3)-2-azido-6-O-benzoyl-2-deoxy-β-D-galactopyranoside 
• 221524-11-4 methyl [2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-5-N,N-diacetylamino-3,5-dideoxy-3-phenylthio-D-erythro-β-L-gluco-non-2-ulopyranosylonate)-(2->8)-5-acetamido-4-O-benzoyl-3,5-dideoxy-9-O-p-methoxybenzyl-D-glycero-α-D-galacto-non-...] 
• 221524-16-9 2-(trimethylsilyl)ethyl (methyl 4,7,8,9-tetra-O-acetyl-5-N,N-diacetylamino-3,5-dideoxy-3-phenylthio-D-erythro-β-L-gluco-non-2-ulopyranosylonate)-(2->3)-(2,6-di-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-acetyl-β-D-xylopyranoside 
• 173911-72-3 methyl (2-(trimethylsilyl)ethyl 5-acetamido-9-azido-4-O-benzoyl-3,5,9-trideoxy-8-O-{methyl [5-acetamido-4,7,8,9-tetra-O-acetyl-3-(phenylthio)-3,5-dideoxy-D-erythro-α-L-gluco-2-nonulopyranosid]onate}-D-glycero-α-D-galacto-2-nonulopyranosid)onate 
• 156727-00-3 2-(Trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<2,4,6-tri-O-benzyl-3-O-onate>-β-D-galactopyranosyl>-β-D-glucopyranoside 

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.

A New N-Acetylneuraminic Acid Donor for Highly Stereoselective α-Sialylation

The new sialyl donor 6 (prepared from N-acetylneuraminic acid in 44percent yield over six steps) effects clean α-sialylation of 2-(trimethylsilyl)ethyl 2,3,6,2',4',6'-hexabenzyl-β-D-lactoside in 67percent yield.