methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxane-2-carboxylate

• ChemBase ID: 134196
• Molecular Formular: C13H17BrO9
• Molecular Mass: 397.17268
• Monoisotopic Mass: 396.00559412
• SMILES: CC(=O)O[C@H]1[C@@H]([C@H](O[C@@H]([C@@H]1OC(=O)C)Br)C(=O)OC)OC(=O)C
• Canonical SMILES: COC(=O)[C@H]1O[C@H](Br)[C@@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C13H17BrO9/c1-5(15)20-8-9(21-6(2)16)11(13(18)19-4)23-12(14)10(8)22-7(3)17/h8-12H,1-4H3/t8-,9-,10+,11-,12-/m0/s1
• InChIKey: GWTNLHGTLIBHHZ-SVNGYHJRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxane-2-carboxylate
• Synonyms: (2,3,4-Tri-O-acetyl-α-D-glucopyranosyl bromide)uronic acid methyl ester; Bromo-2,3,4-tri-O-acetyl-α-D-glucopyranuronic acid methyl ester; Methyl acetobromo-α-D-glucuronate; Acetobromo-α-D-glucuronic acid methyl ester; (2R,3R,4S,5S,6S)-2-Bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate; 1-Bromo-1-deoxy-2,3,4-triacetate α-D-Glucopyranuronic Acid Methyl Ester; Methyl (Tri-O-acetyl-α-D-glucopyranosyl Bromide)uronate; Methyl 2,3,4-Tri-O-acetyl-1-bromo-1-deoxy-α-D-glucopyranuranate; Methyl α-Acetobromoglucuronate; Acetobromo-α-D-glucuronic Acid Methyl Ester

Database IDs

• CAS Number: 21085-72-3
• EC Number: 244-203-4
• MDL Number: MFCD00061613
• Beilstein Number: 96281
• PubChem SID: 24891328; 162228473; 24845062
• PubChem CID: 88785

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.38527408
• LogD (pH = 7.4): -0.38527408
• Log P: -0.38527408
• Molar Refractivity: 74.3686 cm^3
• Polarizability: 31.050533 Å^3
• Polar Surface Area: 114.43 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethyl Sulfoxide; Dimethylformamide; Ethyl Acetate; Methaol
• Apperance: White Solid
• Melting Point: 100-102°C; 80-110 °C(lit.)
• Optical Rotation: [α]20/D +190±10°, c = 1% in ethyl acetate

Safety Information

• Storage Condition: -86°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥93%; ≥95.0% (GC); 95+%
• Grade: purum
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C13H17BrO9

DETAILS

Sigma Aldrich - A8292

Application
Acetobromo-α-D-glucuronic acid methyl ester is used for the synthesis of HMR1098-S-Glucuronide Methyl Ester, a new K-ATP-blocking agent being developed as a drug for prevention of sudden cardiac death.

REFERENCES

• Honda, T., et al.: J. Med. Chem., 31, 1295 (1988)