methyl (2R,3S,4S,5R,6S)-3,4,5,6-tetrakis(acetyloxy)oxane-2-carboxylate

• ChemBase ID: 174326
• Molecular Formular: C15H20O11
• Molecular Mass: 376.3127
• Monoisotopic Mass: 376.10056146
• SMILES: [C@@H]1([C@@H](O[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)C(=O)OC)OC(=O)C)OC(=O)C
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](OC(=O)C)[C@@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C15H20O11/c1-6(16)22-10-11(23-7(2)17)13(24-8(3)18)15(25-9(4)19)26-12(10)14(20)21-5/h10-13,15H,1-5H3/t10-,11-,12+,13+,15+/m0/s1
• InChIKey: DPOQCELSZBSZGX-RLPMIEJPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R,3S,4S,5R,6S)-3,4,5,6-tetrakis(acetyloxy)oxane-2-carboxylate
• IUPAC Traditional name: methyl (2R,3S,4S,5R,6S)-3,4,5,6-tetrakis(acetyloxy)oxane-2-carboxylate
• Synonyms: Methyl 1,2,3,4-Tetra-O-acetyl-α-L-iduronate; α-L-Idopyranuronic Acid Methyl Ester Tetraacetate; Methyl 1,2,3,4-Tetra-O-acetyl-α-L-idopyranuronate

Database IDs

• CAS Number: 108032-41-3
• PubChem SID: 164230236
• PubChem CID: 12275077

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): -0.701869
• LogD (pH = 7.4): -0.701869
• Log P: -0.701869
• Molar Refractivity: 77.1659 cm^3
• Polarizability: 32.614796 Å^3
• Polar Surface Area: 140.73 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 120-122°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Store at -20°C

DETAILS

Toronto Research Chemicals - M326700

Methyl 1,2,3,4-Tetra-O-acetyl-α-L-idopyranuronate is used in the synthesis of L-iduronic acid derivatives from D-glucuronic acid analogs.

REFERENCES

• Chiba, T., et al.: Carbohydr. Res., 151, 379 (1986)