78850-37-0

Basic information

• Product Name: methyl (3aR,4R,7aR)-2-methyl-4-(1S,2R,3-triacetoxypropyl)-3a,7a-dihydro-4H-pyrano[3,4-d]oxazole-6-carboxylate
• Synonyms: methyl (3aR,4R,7aR)-2-methyl-4-(1S,2R,3-triacetoxypropyl)-3a,7a-dihydro-4H-pyrano[3,4-d]oxazole-6-carboxylate;(3aR,4R,7aR)-;(3aR,4R,7aR)-3a,7a-Dihydro-2-Methyl-4-[(1S,2R)-1,2,3-tris(acetyloxy)propyl]-4H-pyrano[3,4-d]oxazole-6-carboxylic Acid Methyl Ester
• CAS NO: 78850-37-0
• Molecular Formula: C₁₈H₂₃NO₁₀
• Molecular Weight: 413.37592
• EINECS: 415-670-3
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Anti-virals
• Mol File: 78850-37-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 469.532°C at 760 mmHg
• Flash Point: 170.889°C
• Appearance: /
• Density: 1.408g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.555
• Solubility: Chloroform, Ethyl Acetate
• PKA: 4.56±0.60(Predicted)
• CAS DataBase Reference: methyl (3aR,4R,7aR)-2-methyl-4-(1S,2R,3-triacetoxypropyl)-3a,7a-dihydro-4H-pyrano[3,4-d]oxazole-6-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (3aR,4R,7aR)-2-methyl-4-(1S,2R,3-triacetoxypropyl)-3a,7a-dihydro-4H-pyrano[3,4-d]oxazole-6-carboxylate(78850-37-0)
• EPA Substance Registry System: methyl (3aR,4R,7aR)-2-methyl-4-(1S,2R,3-triacetoxypropyl)-3a,7a-dihydro-4H-pyrano[3,4-d]oxazole-6-carboxylate(78850-37-0)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• Hazardous Substances Data: 78850-37-0(Hazardous Substances Data)

Usage

Description

Methyl (3aR,4R,7aR)-2-methyl-4-(1S,2R,3-triacetoxypropyl)-3a,7a-dihydro-4H-pyrano[3,4-d]oxazole-6-carboxylate is a complex organic compound characterized by its unique molecular structure. It is a derivative of pyrano[3,4-d]oxazole, a heterocyclic compound with potential applications in various fields due to its chemical properties.

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

• 20298-35-5 N-acetylneuraminic acid methyl ester 
• 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 

Downstream Products

• 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 
• 1453411-79-4 methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-4-amino-3,4,5-trideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate 
• 1453411-78-3 methyl (4-nitrophenyl 5-acetamido-7,8,9-tri-O-acetyl-4-azido-3,4,5-trideoxy-D-glycero-β-D-galactonon-2-ulopyranosid)onate 

Relevant articles and documents

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.