Methyl (6R)-5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-6-[(1S,2R)-1,2,3-triacetoxypropyl]-L-threo-hex-2-enonate | CAS No. 130525-58-5

Methyl (6R)-5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-6-[(1S,2R)-1,2,3-triacetoxypropyl]-L-threo-hex-2-enonate

Basic Information

CAS Number

130525-58-5

Molecular Formula

C18H24N4O10

Molecular Weight

456.4 g/mol

AD

Basic Physical Properties

Melting Point

56-61°C

Solubility

Chloroform, Methanol

CC(=O)NC1C(C=C(OC1C(C(COC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC)N=[N+]=[N-]

InChI

InChI=1S/C18H24N4O10/c1-8(23)20-15-12(21-22-19)6-13(18(27)28-5)32-17(15)16(31-11(4)26)14(30-10(3)25)7-29-9(2)24/h6,12,14-17H,7H2,1-5H3,(H,20,23)/t12-,14+,15+,16+,17+/m0/s1

InChIKey

ANKWFOHGBMGGAL-IIHMKKKESA-N

LogP

-0.10414

Complexity

836

Synonyms & References

English

  • Zanamivir Azide Triacetate Methyl Ester
  • CS-0081277
  • methyl (2R,3R,4S)-3-acetamido-4-azido-2-[(1S,2R)-1,2,3-triacetyloxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate
  • MFCD08704809
  • 5-(Acetylamino)-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic Acid Methyl Ester 7,8,9-Triacetate
  • 130525-58-5
  • Methyl 7,8,9-tri-o-acetyl-N-acetyl-2-deoxy-2,3-didehydro-4a-azido-D-neuraminate
  • (4S,5R,6R)-5-ACETYLAMINO-4-AZIDO-6-(1S,2R,3-TRIACETOXYPROPYL)-5,6-DIHYDRO-4H-PYRAN-2-CARBOXYLIC ACID
  • SCHEMBL15045962
  • D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID
  • D95530
  • ANKWFOHGBMGGAL-IIHMKKKESA-N
  • D-glycero-D-galacto-Non-2-enonic acid, 5-(acetylamino)-2,6-anhydro-4-azido-3,4,5-trideoxy-, methyl ester, 7,8,9-triacetate
  • (1S,2R)-1-((2R,3R,4S)-3-acetamido-4-azido-6-(methoxycarbonyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate
  • Methyl 5-acetamido-7,8,9-O-triacetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonat
  • Q-102537
  • AS-76958
  • Methyl 5-acetamido-7,8,9-O-triacetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonate
  • D-GLYCERO-D-GALACTO-NON-2-ENONIC ACID,ENTERPRISE STANDARD
  • Zanamivir Azide Tria
  • ZanaMivir Azide
  • ZanaMivir interMediate3
  • Zanamivir intermediate D4
  • Methyl7,8,9-tri-O-acetyl-N-acetyl-2-deoxy-2,3-didehydro-4a-azido-D-neuraminate
  • 5-(acetylamino)-2,6-anhydro-4-azido-3,4,5-trideoxy-,methyl ester, 7,8,9-triacetate
  • Methyl 5-acetaMido-7,8,9-O-triacetyl-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonat
  • 5-(AcetylaMino)-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic Acid Methyl Ester 7,8,9-Triacetate

MDL Number

MFCD08704809

FAQ

What are the physical and chemical properties of Methyl (6R)-5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-6-[(1S,2R)-1,2,3-triacetoxypropyl]-L-threo-hex-2-enonate (CAS: 130525-58-5)?

The compound is a crystalline solid with a molecular weight of approximately 631.5 g/mol. It is slightly soluble in water but highly soluble in organic solvents like methanol and DMSO. Chemically, it is reactive due to the presence of acetamido, azido, and acetoxy groups. It is stable in neutral and slightly acidic conditions but should be handled with care in basic environments.

How is Methyl (6R)-5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-6-[(1S,2R)-1,2,3-triacetoxypropyl]-L-threo-hex-2-enonate (CAS: 130525-58-5) typically synthesized?

The compound can be synthesized through a multi-step process involving acetylation, azidation, and esterification reactions. The key steps include the protection of hydroxyl groups, followed by selective functionalization. The reaction conditions typically involve the use of acetic anhydride and sodium azide, with suitable catalysts and solvents to achieve high yield and selectivity.

What industries use Methyl (6R)-5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-6-[(1S,2R)-1,2,3-triacetoxypropyl]-L-threo-hex-2-enonate (CAS: 130525-58-5)?

This compound is primarily used in the pharmaceutical and chemical research industries for its unique functional groups. It may find applications in the development of new drugs, as a building block for complex molecules, and in the synthesis of biosensors and other medical devices. Its reactivity makes it suitable for use in custom chemical synthesis and academic research.

What precautions should be taken when handling Methyl (6R)-5-acetamido-2,6-anhydro-4-azido-3,4,5-trideoxy-6-[(1S,2R)-1,2,3-triacetoxypropyl]-L-threo-hex-2-enonate (CAS: 130525-58-5)?

When handling this compound, laboratory personnel should wear appropriate personal protective equipment (PPE), including gloves, goggles, and a lab coat. It should be stored in a fume hood and away from heat and oxidizing agents. In case of a spill, it should be cleaned up immediately according to the Material Safety Data Sheet (MSDS) guidelines. Always refer to the latest SDS for updated safety information.

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