(4S)-4-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolane

• ChemBase ID: 152221
• Molecular Formular: C13H18O3
• Molecular Mass: 222.28022
• Monoisotopic Mass: 222.12559444
• SMILES: CC1(OC[C@@H](O1)COCc1ccccc1)C
• Canonical SMILES: CC1(C)OC[C@@H](O1)COCc1ccccc1
• InChI: InChI=1S/C13H18O3/c1-13(2)15-10-12(16-13)9-14-8-11-6-4-3-5-7-11/h3-7,12H,8-10H2,1-2H3/t12-/m0/s1
• InChIKey: DBFDSKSLTCMIPB-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolane
• IUPAC Traditional name: (4S)-4-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolane
• Synonyms: 3-Benzyl-1,2-isopropylidene-sn-glycerol; D-α,β-Isopropylideneglycerol-γ-benzyl ether; (S)-4-Benzyloxymethyl-2,2-dimethyl-1,3-dioxolane; (4S)-2,2-Dimethyl-4-[(phenylmethoxy)methyl]-1,3-dioxolane; 1,2-Isopropylidene-3-O-benzyl-sn-glycerol; (S)-4-[(Benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolane; (S)-1-Benzyl-2,3-O-isopropylidene Glycerol; 3-苄基-1,2-异亚丙基-sn-甘油; D-α,β-异亚丙基甘油-γ-苄醚; (S)-4-苄氧甲基-2,2-二甲基-1,3-二氧戊环

Database IDs

• CAS Number: 16495-03-7
• MDL Number: MFCD00043000
• Beilstein Number: 82963
• PubChem SID: 162246366; 24881507
• PubChem CID: 10878747

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.2310102
• LogD (pH = 7.4): 2.2310102
• Log P: 2.2310102
• Molar Refractivity: 62.0869 cm^3
• Polarizability: 24.560461 Å^3
• Polar Surface Area: 27.69 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Clear Yellow Oil
• Boiling Point: 79-80 °C/0.05 mmHg(lit.)
• Flash Point: 100 °C; 212 °F
• Density: 1.050 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.496
• Optical Rotation: [α]20/D +21±1°, c = 4% in chloroform

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (sum of enantiomers, GC)
• Empirical Formula (Hill Notation): C13H18O3

DETAILS

Sigma Aldrich - 59442

Other Notes
Chiral building block; synthesis of chiral glycerides1,2,3,4
Packaging
5 mL in glass bottle

Toronto Research Chemicals - B281010

Used in the preparation of the analogs of dioxolanes Dexoxadrol and Etoxadrol as potential phencyclidine-like agents.

REFERENCES

• Nacro, K., et al.: Bioorg. Med. Chem. Lett., 10, 1401 (2000)
• Rodriguez, J., et al.: Anal. Biochem., 375, 196 (2000)