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

• ChemBase ID: 174357
• Molecular Formular: C9H19NO5S
• Molecular Mass: 253.31586
• Monoisotopic Mass: 253.09839371
• SMILES: [C@H]1([C@@H]([C@@H]([C@H](O[C@H]1[C@@H]([C@H](O)C)N)SC)O)O)O
• Canonical SMILES: CS[C@H]1O[C@@H]([C@@H]([C@H](O)C)N)[C@@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C9H19NO5S/c1-3(11)4(10)8-6(13)5(12)7(14)9(15-8)16-2/h3-9,11-14H,10H2,1-2H3/t3-,4-,5+,6-,7-,8-,9-/m1/s1
• InChIKey: AEEIMWYSDWZKAT-HJTGYUAHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R,6R)-2-[(1R,2R)-1-amino-2-hydroxypropyl]-6-(methylsulfanyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4S,5R,6R)-2-[(1R,2R)-1-amino-2-hydroxypropyl]-6-(methylsulfanyl)oxane-3,4,5-triol
• Synonyms: Methyl 6-Amino-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside; Methyl α-Thiolincosaminide; Methyl 1-Thiolincosaminide

Database IDs

• CAS Number: 14810-93-6
• PubChem SID: 164230267
• PubChem CID: 22294670

CALCULATED PROPERTIES

• Acid pKa: 12.490366
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -4.647918
• LogD (pH = 7.4): -3.0883846
• Log P: -1.8990632
• Molar Refractivity: 58.8336 cm^3
• Polarizability: 24.470695 Å^3
• Polar Surface Area: 116.17 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Off-White to Pale Beige Solid
• Melting Point: 185-188°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M330735

Intermediate in the production of biosynthetic antibiotics

REFERENCES

• Horton, D., et al.: Anal. Biochem., 59, 452 (1974)
• Kamenik, Z., et al.: Anal. Bioanal. Chem., 393, 1779 (1974)