(2S,3S,4S,6R)-4-amino-6-methoxy-2-methyloxan-3-ol

• ChemBase ID: 173499
• Molecular Formular: C7H15NO3
• Molecular Mass: 161.1989
• Monoisotopic Mass: 161.10519335
• SMILES: [C@H]1([C@H]([C@H](C[C@@H](O1)OC)N)O)C
• Canonical SMILES: CO[C@H]1C[C@H](N)[C@@H]([C@H](O1)C)O
• InChI: InChI=1S/C7H15NO3/c1-4-7(9)5(8)3-6(10-2)11-4/h4-7,9H,3,8H2,1-2H3/t4-,5-,6+,7+/m0/s1
• InChIKey: UIWJWFKPPXKEJV-VWDOSNQTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,6R)-4-amino-6-methoxy-2-methyloxan-3-ol
• IUPAC Traditional name: (2S,3S,4S,6R)-4-amino-6-methoxy-2-methyloxan-3-ol
• Synonyms: Methyl 3-Αmino-2,3,6-trideoxy-α-L-lyxohexopyranoside Hydrochloride; α-Methyl Daunosaminide Hydrochloride; Methyl α-L-Daunosamine Hydrochloride (α:β approx. 85:15)

Database IDs

• CAS Number: 32385-06-1
• PubChem SID: 164229409
• PubChem CID: 3081447

CALCULATED PROPERTIES

• Acid pKa: 13.615076
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.4501855
• LogD (pH = 7.4): -2.6381607
• Log P: -0.44874647
• Molar Refractivity: 39.2777 cm^3
• Polarizability: 16.46614 Å^3
• Polar Surface Area: 64.71 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Off-White Powder
• Melting Point: 175-178°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M294800

Methyl α-L-Daunosamine is used in the synthesis of (L)-Daunosamine and related amino sugars.

REFERENCES

• Di Marco, A., et al.: Tumori, 49, 203 (1963)
• Nagumo, S., et al.: Chem. Pharm. Bull., 43, 171 (1963)