[(4R,5R)-5-(hydroxymethyl)-2-phenyl-1,3-dioxolan-4-yl]methanol

• ChemBase ID: 156637
• Molecular Formular: C11H14O4
• Molecular Mass: 210.22646
• Monoisotopic Mass: 210.08920893
• SMILES: c1ccc(cc1)C1O[C@@H]([C@H](O1)CO)CO
• Canonical SMILES: OC[C@H]1OC(O[C@@H]1CO)c1ccccc1
• InChI: InChI=1S/C11H14O4/c12-6-9-10(7-13)15-11(14-9)8-4-2-1-3-5-8/h1-5,9-13H,6-7H2/t9-,10-/m1/s1
• InChIKey: AEJRVTSEJAYBNR-NXEZZACHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(4R,5R)-5-(hydroxymethyl)-2-phenyl-1,3-dioxolan-4-yl]methanol
• IUPAC Traditional name: [(4R,5R)-5-(hydroxymethyl)-2-phenyl-1,3-dioxolan-4-yl]methanol
• Synonyms: (4R,5R)-(+)-2-Phenyl-1,3-dioxolane-4,5-dimethanol; (+)-2,3-O-Benzylidene-D-threitol; (4R,5R)-(+)-2-苯基-1,3-二氧戊环-4,5-二甲醇; (+)-2,3-O-亚苄基-D-苏糖醇

Database IDs

• CAS Number: 58383-35-0
• MDL Number: MFCD00010198
• Beilstein Number: 5433394
• PubChem SID: 24848178; 162250774
• PubChem CID: 719729

CALCULATED PROPERTIES

• Acid pKa: 14.281761
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.69573027
• LogD (pH = 7.4): 0.6957302
• Log P: 0.69573027
• Molar Refractivity: 53.3622 cm^3
• Polarizability: 21.451094 Å^3
• Polar Surface Area: 58.92 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 70-72 °C; 70-72 °C(lit.)
• Optical Rotation: [α]20/D +11±1°, c = 2% in methanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (sum of enantiomers, HPLC)
• Grade: purum
• Empirical Formula (Hill Notation): C11H14O4

DETAILS

Sigma Aldrich - 13473

Other Notes
Chiral building block1; Bromination of the dibenzyl ether to the 2-bromo-3-benzoate derivative2; Deoxygenation of the hydroxy groups3; Cleavage of acetal to benzyl ether in derivatives4