(2S,3R,4S,5R,6S)-5-azido-4-(benzoyloxy)-2-methoxy-6-[(triphenylmethoxy)methyl]oxan-3-yl benzoate

• ChemBase ID: 173325
• Molecular Formular: C40H35N3O7
• Molecular Mass: 669.7218
• Monoisotopic Mass: 669.24750048
• SMILES: [C@@H]1([C@@H]([C@@H]([C@H](O[C@H]1COC(c1ccccc1)(c1ccccc1)c1ccccc1)OC)OC(=O)c1ccccc1)OC(=O)c1ccccc1)N=[N+]=[N-]
• Canonical SMILES: [N-]=[N+]=N[C@@H]1[C@H](COC(c2ccccc2)(c2ccccc2)c2ccccc2)O[C@@H]([C@H]([C@H]1OC(=O)c1ccccc1)OC(=O)c1ccccc1)OC
• InChI: InChI=1S/C40H35N3O7/c1-46-39-36(50-38(45)29-19-9-3-10-20-29)35(49-37(44)28-17-7-2-8-18-28)34(42-43-41)33(48-39)27-47-40(30-21-11-4-12-22-30,31-23-13-5-14-24-31)32-25-15-6-16-26-32/h2-26,33-36,39H,27H2,1H3/t33-,34-,35+,36-,39+/m1/s1
• InChIKey: XSCBEOKIHHOARQ-JUVZPEBASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5R,6S)-5-azido-4-(benzoyloxy)-2-methoxy-6-[(triphenylmethoxy)methyl]oxan-3-yl benzoate
• IUPAC Traditional name: (2S,3R,4S,5R,6S)-5-azido-4-(benzoyloxy)-2-methoxy-6-[(triphenylmethoxy)methyl]oxan-3-yl benzoate
• Synonyms: Methyl 4-Azido-4-deoxy-6-O-trityl-2,3-dibenzoate α-D-Glucopyranoside; Methyl 4-Azido-2,3-di-O-benzoyl-4-deoxy-6-O-trityl-α-D-glucopyranoside

Database IDs

• CAS Number: 26511-50-2
• PubChem SID: 164229235
• PubChem CID: 71750202

CALCULATED PROPERTIES

• Acid pKa: 14.9261675
• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 9.207567
• LogD (pH = 7.4): 9.207567
• Log P: 9.321613
• Molar Refractivity: 186.4125 cm^3
• Polarizability: 72.1815 Å^3
• Polar Surface Area: 109.72 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: White to Off-White Solid
• Melting Point: 162-164°C

Safety Information

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

DETAILS

Toronto Research Chemicals - M288725

Used as intermediate for synthesis in nucleoside antibiotics.

REFERENCES

• Naka, T., et al.: Agr. Biol. Chem., 34, 1855 (1970)
• Watanabe, A., et al.: Carbohydrate Res., 21, 148 (1970)