78850-37-0

Usage

Uses

Used in Pharmaceutical Industry:
Methyl (3aR,4R,7aR)-2-methyl-4-(1S,2R,3-triacetoxypropyl)-3a,7a-dihydro-4H-pyrano[3,4-d]oxazole-6-carboxylate is used as an intermediate in the preparation of Zanamivir derivatives. Zanamivir is an antiviral medication used for the treatment of influenza A and B. methyl (3aR,4R,7aR)-2-methyl-4-(1S,2R,3-triacetoxypropyl)-3a,7a-dihydro-4H-pyrano[3,4-d]oxazole-6-carboxylate plays a crucial role in the synthesis of Zanamivir-related drugs, contributing to the development of effective treatments for viral infections.

InChI:InChI=1/C18H23NO10/c1-8-19-15-12(26-8)6-13(18(23)24-5)29-17(15)16(28-11(4)22)14(27-10(3)21)7-25-9(2)20/h6,12,14-17H,7H2,1-5H3/t12-,14-,15-,16-,17-/m1/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 
• 20298-35-5 N-acetylneuraminic acid methyl ester 
• 108-24-7 acetic anhydride 

Downstream Products

• 130525-58-5 methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate 
• 1072449-83-2 methyl (3aS,4R,7aR)-4-[(1R,2R)-1,2,3-trihydroxy-propyl]-2-methyl-3a,7a-dihydro-4H-pyrano[3,4-d][1,3]oxazole-6-carboxylate 
• 1453411-74-9 4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-guanidino-α-D-glycero-D-galacto-non-2-ulpyranosylonic acid 
• 1453411-73-8 4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-isopropylamino-α-D-glycero-D-galacto-non-2-ulopyranosylonic acid 
• 1453411-72-7 4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-dimethylamino-α-D-glycero-D-galacto-non-2-ulpyranosylonic acid 
• 1453411-71-6 4-nitrophenyl 4,5-diacetamido-3,4,5-trideoxy-α-D-glycero-D-galacto-non-2-ulpyranosylonic acid 
• 1453411-70-5 4-nitrophenyl 5-acetamido-4-amino-3,4,5-trideoxy-α-D-glycero-D-galacto-non-2-ulpyranosylonic acid 
• 1453411-69-2 4-nitrophenyl 5-acetamido-3,4,5-trideoxy-4-(1-triazolyl)-α-D-glycero-D-galacto-non-2-ulpyranosylonic acid 
• 1453411-68-1 4-nitrophenyl 5-acetamido-4-azido-3,4,5-trideoxy-α-D-glycero-D-galacto-non-2-ulpyranosylonic acid 
• 1453411-84-1 methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-4-[2,3-bis(tert-butoxycarbonyl)guanidino]-3,4,5-trideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate 
• 1453411-83-0 methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-3,4,5-trideoxy-4-isopropylamino-D-glycero-α-D-galacto-non-2-ulopyranosid)onate 
• 1453411-82-9 methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-3,4,5-trideoxy-4-dimethylamino-D-glycero-α-D-galacto-non-2-ulopyranosid)onate 
• 1453411-81-8 methyl (4-nitrophenyl 4,5-diacetamido-7,8,9-tri-O-acetyl-3,4,5-trideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate 
• 1453411-80-7 methyl (4-nitrophenyl 5-acetamido-4-(1-triazolyl)-3,4,5-trideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate 

Relevant academic research and scientific papers

Selective synthesis of Neu5Ac2en and its oxazoline derivative using BF3·Et2O

Application of the Lewis acid BF3·Et2O to the selective synthesis of 5-acetamido-2,6-anhydro-3,5-dideoxy-d-glycero-d-galacto-non-2-enonic acid (Neu5Ac2en) and the related oxazoline, methyl 7,8,9-tri-O-acetyl-2,3,4,5-tetradeoxy-2,3-didehydro-2,3-trideoxy-4′,5′-dihydro-2′-methyloxazolo[5,4-d]- d-glycero-d-talo-non-2-enonate is described.

A synthesis of N-acetylneuraminic acid and [6-2H]-N-acetylneuraminic acid from N-acetyl-D-glucosamine.

N-Acetylneuraminic acid (Neu5Ac) and [6-2H]-Neu5Ac were prepared from 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine). Then Henry reaction of a 1-deoxy-1-nitro derivative of GlcNAc (protected 1-C-nitroanhydro-D-glucitol) with cyclohexylidene-D-glyceraldehyde, followed by successive acetylation and reductive denitration with Bu3SnH, gave an anhydrononitol intermediate (6) diastereo-selectively in high yields. Debenzylidenation of 6 freed its distal primary carbinol group, which was subjected to catalytic oxidation followed by hydrolysis, esterification (diazomethane), and acetylation to give a protected methyl nononate. This ester was transformed into the known methyl N-acetyl-4,7,8,9-tetra-O-acetyl-2,3-dehydroneuraminate (15), which was identical with a sample prepared from Neu5Ac. Neu5Ac was obtained from 15 by bromoetherification (NBS, methanol) followed by reductive debromination with Bu3SnH and hydrolysis. Similarly, the [6-2H]-derivative of 15 was transformed into [6-2H]-Neu5Ac.