[(2R,3S,4R,5R)-3,4-bis(acetyloxy)-6-bromo-5-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)oxan-2-yl]methyl acetate

• ChemBase ID: 162818
• Molecular Formular: C20H20BrNO9
• Molecular Mass: 498.2781
• Monoisotopic Mass: 497.03214323
• SMILES: [C@@H]1([C@@H]([C@@H](C(O[C@H]1COC(=O)C)Br)N1C(=O)c2ccccc2C1=O)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@H]1[C@H](OC(=O)C)[C@H](COC(=O)C)OC([C@H]1N1C(=O)c2c(C1=O)cccc2)Br
• InChI: InChI=1S/C20H20BrNO9/c1-9(23)28-8-14-16(29-10(2)24)17(30-11(3)25)15(18(21)31-14)22-19(26)12-6-4-5-7-13(12)20(22)27/h4-7,14-18H,8H2,1-3H3/t14-,15-,16-,17-,18?/m1/s1
• InChIKey: GRDUQQNEXMJRRS-XNIMBYMISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4R,5R)-3,4-bis(acetyloxy)-6-bromo-5-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4R,5R)-3,4-bis(acetyloxy)-6-bromo-5-(1,3-dioxoisoindol-2-yl)oxan-2-yl]methyl acetate
• Synonyms: 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-D-glucopyranosyl Bromide 3,4,6-Triacetate; Bromo 2-Deoxy-2-N-phthalimido-3,4,6-tri-O-acetyl-α,β-D-glucopyranoside

Database IDs

• CAS Number: 70831-94-6
• PubChem SID: 162256953
• PubChem CID: 10696647

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 0.46911132
• LogD (pH = 7.4): 0.46911132
• Log P: 0.46911132
• Molar Refractivity: 105.6823 cm^3
• Polarizability: 41.670437 Å^3
• Polar Surface Area: 125.51 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane,Ethanol; Ethyl Acetate; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 124-128°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B683000

Used for the synthesis of β-D-N-acetyl glucosamine glycosidic linkages.

REFERENCES

• Am. Chem. Symp. Ser., 39, 90, (1976)