(2R,3R,4S,5R,6R)-2-[(1S,2S)-1-amino-2-chloropropyl]-6-(methylsulfanyl)oxane-3,4,5-triol

• ChemBase ID: 173462
• Molecular Formular: C9H18ClNO4S
• Molecular Mass: 271.76152
• Monoisotopic Mass: 271.06450674
• SMILES: [C@H]1([C@@H]([C@@H]([C@H](O[C@H]1[C@@H]([C@@H](Cl)C)N)SC)O)O)O
• Canonical SMILES: CS[C@H]1O[C@@H]([C@@H]([C@@H](Cl)C)N)[C@@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C9H18ClNO4S/c1-3(10)4(11)8-6(13)5(12)7(14)9(15-8)16-2/h3-9,12-14H,11H2,1-2H3/t3-,4+,5-,6+,7+,8+,9+/m0/s1
• InChIKey: TVVQUVMUAMNLLX-WCFBUKAXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R,6R)-2-[(1S,2S)-1-amino-2-chloropropyl]-6-(methylsulfanyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4S,5R,6R)-2-[(1S,2S)-1-amino-2-chloropropyl]-6-(methylsulfanyl)oxane-3,4,5-triol
• Synonyms: Methyl 6-Amino-7-chloro-6,7,8-trideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside; Methyl 7-Chloro-7-deoxy-1-thiolincosaminide

Database IDs

• CAS Number: 22965-79-3
• PubChem SID: 164229372
• PubChem CID: 53485980

CALCULATED PROPERTIES

• Acid pKa: 12.492843
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -3.055369
• LogD (pH = 7.4): -1.3757694
• Log P: -0.5444714
• Molar Refractivity: 61.8846 cm^3
• Polarizability: 25.691162 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - M294505

Intermediate in the preparation of lincomycin derived antibiotics.

REFERENCES

• Alexander, J., et al.: J. Med. Chem., 39, 480 (1996)