(2S,3S,4S,5S,6R)-2-azido-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 154179
• Molecular Formular: C6H11N3O5
• Molecular Mass: 205.16864
• Monoisotopic Mass: 205.06987047
• SMILES: C([C@@H]1[C@H]([C@@H]([C@@H]([C@H](O1)N=[N+]=[N-])O)O)O)O
• Canonical SMILES: [N-]=[N+]=N[C@H]1O[C@H](CO)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C6H11N3O5/c7-9-8-6-5(13)4(12)3(11)2(1-10)14-6/h2-6,10-13H,1H2/t2-,3-,4+,5+,6+/m1/s1
• InChIKey: KSRDTSABQYNYMP-PQMKYFCFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5S,6R)-2-azido-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,3S,4S,5S,6R)-2-azido-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: α-D-Mannopyranosyl azide

Database IDs

• MDL Number: MFCD05865236
• PubChem SID: 162248318
• PubChem CID: 54011468

CALCULATED PROPERTIES

• Acid pKa: 12.353503
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.2262404
• LogD (pH = 7.4): -2.2262452
• Log P: -2.1121948
• Molar Refractivity: 42.2159 cm^3
• Polarizability: 16.860182 Å^3
• Polar Surface Area: 119.58 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 1
• Safety Statements: 22-24/25
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (TLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C6H11N3O5

DETAILS

Sigma Aldrich - M6691

Application
Used to make N-link glycopeptides in glycobiology.