2-chloro-1-[(1R,3S,4S,5S,8S)-4,8-dihydroxy-3-methoxy-2-oxa-6-azabicyclo[3.2.1]octan-6-yl]ethan-1-one

• ChemBase ID: 173550
• Molecular Formular: C9H14ClNO5
• Molecular Mass: 251.66416
• Monoisotopic Mass: 251.05605023
• SMILES: [C@@H]12[C@H]([C@@H]([C@@H]([C@H](O1)OC)O)N(C2)C(=O)CCl)O
• Canonical SMILES: CO[C@H]1O[C@@H]2CN([C@H]([C@@H]1O)[C@@H]2O)C(=O)CCl
• InChI: InChI=1S/C9H14ClNO5/c1-15-9-8(14)6-7(13)4(16-9)3-11(6)5(12)2-10/h4,6-9,13-14H,2-3H2,1H3/t4-,6+,7-,8+,9+/m1/s1
• InChIKey: OOLIJRCIVXLOFW-WTZHZCGUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-chloro-1-[(1R,3S,4S,5S,8S)-4,8-dihydroxy-3-methoxy-2-oxa-6-azabicyclo[3.2.1]octan-6-yl]ethan-1-one
• IUPAC Traditional name: 2-chloro-1-[(1R,3S,4S,5S,8S)-4,8-dihydroxy-3-methoxy-2-oxa-6-azabicyclo[3.2.1]octan-6-yl]ethanone
• Synonyms: [1R-(3-exo,4-endo,8-syn)]-6-(Chloroacetyl)-3-methoxy-2-oxa-6-azabicyclo[3.2.1]octane-4,8-diol; Methyl-3,6-dideoxychloroacetamido-α-D-mannopyranoside

Database IDs

• CAS Number: 172926-30-6
• PubChem SID: 164229460
• PubChem CID: 11097050

CALCULATED PROPERTIES

• Acid pKa: 12.654416
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.297851
• LogD (pH = 7.4): -1.2978534
• Log P: -1.297851
• Molar Refractivity: 53.1645 cm^3
• Polarizability: 21.804077 Å^3
• Polar Surface Area: 79.23 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Brown Liquid

DETAILS

Toronto Research Chemicals - M301550

Methyl-3,6-dideoxychloroacetamido-α-D-mannopyranoside is used in the process for the preparation of immunostimulating swainsonine analogs.