[(3S,5S,6S)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate

• ChemBase ID: 301955
• Molecular Formular: C14H19BrO9
• Molecular Mass: 411.19926
• Monoisotopic Mass: 410.02124419
• SMILES: CC(=O)OCC1[C@@H](C([C@@H]([C@@H](O1)Br)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)OCC1O[C@@H](Br)[C@H](C([C@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C14H19BrO9/c1-6(16)20-5-10-11(21-7(2)17)12(22-8(3)18)13(14(15)24-10)23-9(4)19/h10-14H,5H2,1-4H3/t10?,11-,12?,13-,14+/m0/s1
• InChIKey: CYAYKKUWALRRPA-YCKYNJIMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(3S,5S,6S)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate
• IUPAC Traditional name: [(3S,5S,6S)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate
• Synonyms: 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide; Acetobromo-alpha-D-glucose; 乙酰溴-alpha-D-葡萄糖

Database IDs

• CAS Number: 572-09-8
• EC Number: 209-339-0
• MDL Number: MFCD00063254
• Beilstein Number: 96669
• Merck Index: 1460

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.3887714
• LogD (pH = 7.4): -0.3887714
• Log P: -0.3887714
• Molar Refractivity: 78.8836 cm^3
• Polarizability: 32.837383 Å^3
• Polar Surface Area: 114.43 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 84-89°C
• Optical Rotation: +198 (c=3 in chloroform)

Safety Information

• Storage Warning: Moisture Sensitive
• TSCA Listed: 否

Product Information

• Purity: 97%, stab. with 2% calcium carbonate

REFERENCES

• Glycosyl isothiocyanates have been prepared in good yield by heating fully O-acetylated glycosyl bromides with KSCN in the absence of solvent. With acetobromo-ɑ-D-glucose, displacement was accompanied by stereochemical inversion: Synthesis, 1228 (1995).
• Reaction with Bis(cyclopentadienyl)titanium dichloride, A11456 results in 1,2-elimination providing a convenient route to the glycal: J. Org. Chem., 60, 7055 (1995).