121512-94-5

Basic information

• Product Name: O-ethyl S-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] dithiocarbonate
• Synonyms: O-ethyl S-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] dithiocarbonate
• CAS NO: 121512-94-5
• Molecular Weight: 595.646
• Mol File: 121512-94-5.mol

Chemical Properties

• CAS DataBase Reference: O-ethyl S-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] dithiocarbonate(CAS DataBase Reference)
• NIST Chemistry Reference: O-ethyl S-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] dithiocarbonate(121512-94-5)
• EPA Substance Registry System: O-ethyl S-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] dithiocarbonate(121512-94-5)

Safety Data

• Hazardous Substances Data: 121512-94-5(Hazardous Substances Data)

Upstream product

• 67670-69-3 N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 
• 140-89-6 potassium ethyl xanthogenate 

Downstream Products

• 156727-01-4 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 
• 156727-02-5 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 
• 139639-79-5 C₅₅H₆₄BrNO₂₆ 
• 139244-26-1 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-<2-azido-6-O-benzyl-2-deoxy-3-O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylate)-β-D-galactopyranosyl>-β-D-glucopyranoside 
• 121512-91-2 methyl (ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid)onate 
• 73960-72-2 methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 
• 191589-28-3 allyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-(2->6)-4-O-acetyl-3-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside 
• 197144-14-2 C₆₆H₉₄N₄O₂₉ 

Relevant articles and documents

Stereoselective α-sialylation with sialyl xanthate and phenylsulfenyl triflate as a promotor

Reaction α- and β-xanthates 2 and 3 of sialic acid with glycosyl acceptors 5-8 in the presence phenylsulfenyl triflate (PST) as a promoter in a 2:1 mixture of CH3CN/CH2Cl2 at low temperature affords α-sialosides in good yield and stereoselectivity. PST is prepared-in. situ by reacting benzenesulfenyl chloride with silver triflate. Less reactive acceptors 5 and 6 give a higher α/β ratio than more reactive allylic alcohol 7 and primary alcohol 8; α-stereoselectivity is increased in a dilute solution. A possible mechanism of the reaction that involves intermediate α- and β-nitrilium cations 16 and 17 is discussed.

Stereoselective synthesis of 2-thioglycosides of N-acetylneuraminic acid

Treatment of methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosonate (1) severally with thiophenol, phenylmethanethiol, and ethanethiol in the presence of boron trifluoride etherate gave the corresponding 2-thio-β-glycosides 3-5.Treatment of methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosyl chloride)onate (2) severally with thiophenol in the presence of N,N-di-isopropylethylamine, O-ethyl S-potassium dithiocarbonate, and O-ethyl S-potassium thiocarbonate gave the corresponding 2-thio-α-glycosides, 7, 10, and 11, of which 10 was converted into the ethyl 2-thio-α-glycoside 9 on heating with N,N-dimethylformamide-sodium iodide.The phenyl 2-thioglycosides 3 and 7 were converted into the corresponding sulfones.