(4R,5R)-4-[(4R,5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl]-2-phenyl-1,3-dioxan-5-ol

• ChemBase ID: 152005
• Molecular Formular: C20H22O6
• Molecular Mass: 358.38508
• Monoisotopic Mass: 358.14163842
• SMILES: c1ccc(cc1)C1OC[C@H]([C@@H](O1)[C@H]1[C@@H](COC(O1)c1ccccc1)O)O
• Canonical SMILES: O[C@@H]1COC(O[C@H]1[C@@H]1OC(OC[C@H]1O)c1ccccc1)c1ccccc1
• InChI: InChI=1S/C20H22O6/c21-15-11-23-19(13-7-3-1-4-8-13)25-17(15)18-16(22)12-24-20(26-18)14-9-5-2-6-10-14/h1-10,15-22H,11-12H2/t15-,16-,17-,18-,19?,20?/m1/s1
• InChIKey: NVEGGHPETXMRSV-NIJYPJQDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,5R)-4-[(4R,5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl]-2-phenyl-1,3-dioxan-5-ol
• IUPAC Traditional name: (4R,5R)-4-[(4R,5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl]-2-phenyl-1,3-dioxan-5-ol
• Synonyms: 1,3:4,6-Di-O-benzylidene-D-mannitol; 1,3:4,6-二-O-苄烯-D-甘露醇

Database IDs

• CAS Number: 28224-73-9
• MDL Number: MFCD18910001
• Beilstein Number: 1627753
• PubChem SID: 24860484; 162246151
• PubChem CID: 9946856

CALCULATED PROPERTIES

• Acid pKa: 13.022294
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.6001396
• LogD (pH = 7.4): 2.6001387
• Log P: 2.6001396
• Molar Refractivity: 92.1708 cm^3
• Polarizability: 37.21387 Å^3
• Polar Surface Area: 77.38 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 192-195 °C
• Optical Rotation: [α]20/D -8.4±0.3°, c = 1% in acetone

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)
• Empirical Formula (Hill Notation): C20H22O6

DETAILS

Sigma Aldrich - 33750

Other Notes
Starting component for the synthesis of optically active glycerol derivatives with a minimum of protective group chemistry1,2; Synthesis of heterocyclic 2,5-dimethanol derivatives3,4
Packaging
5 g in glass bottle