(2R,3R,4R)-2-(hydroxymethyl)-3,4-dihydro-2H-pyran-3,4-diol

• ChemBase ID: 105538
• Molecular Formular: C6H10O4
• Molecular Mass: 146.1412
• Monoisotopic Mass: 146.0579088
• SMILES: O[C@@H]1[C@H](O)C=CO[C@@H]1CO
• Canonical SMILES: OC[C@H]1OC=C[C@H]([C@H]1O)O
• InChI: InChI=1S/C6H10O4/c7-3-5-6(9)4(8)1-2-10-5/h1-2,4-9H,3H2/t4-,5-,6-/m1/s1
• InChIKey: YVECGMZCTULTIS-HSUXUTPPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R)-2-(hydroxymethyl)-3,4-dihydro-2H-pyran-3,4-diol
• IUPAC Traditional name: (2R,3R,4R)-2-(hydroxymethyl)-3,4-dihydro-2H-pyran-3,4-diol
• Synonyms: D-Galactal; 1,5-Anhydro-2-deoxy-D-lyxo-hex-1-enitol; D-GALACTAL; D-半乳醛; D-半乳糖烯

Database IDs

• CAS Number: 21193-75-9
• EC Number: 244-264-7
• MDL Number: MFCD00038067
• Beilstein Number: 81690
• PubChem SID: 162092529; 24869955
• PubChem CID: 2734735

CALCULATED PROPERTIES

• Acid pKa: 12.961105
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.6373401
• LogD (pH = 7.4): -1.6373413
• Log P: -1.6373401
• Molar Refractivity: 33.7791 cm^3
• Polarizability: 13.478408 Å^3
• Polar Surface Area: 69.92 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 99-102 °C; 99-103 °C(lit.)
• Optical Rotation: [α]20/D -21.5±1°, c = 1.2% in methanol; [α]22/D -21.5°, c = 1.2 in methanol

Safety Information

• Storage Condition: 2-8°C
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (sum of enantiomers, GC); 95%
• Grade: purum
• Impurities: ~10% water; ~5% Ethyl acetate
• Empirical Formula (Hill Notation): C6H10O4

DETAILS

Sigma Aldrich - 462233

Application
Important building block for both solution- and solid-phase synthesis of oligosaccharides.1
Packaging
1 g in glass bottle

Sigma Aldrich - 48225

Other Notes
Selective derivatization1,2