(2R)-2-[(triphenylmethoxy)methyl]oxirane

• ChemBase ID: 150962
• Molecular Formular: C22H20O2
• Molecular Mass: 316.393
• Monoisotopic Mass: 316.14632988
• SMILES: c1ccc(cc1)C(c1ccccc1)(c1ccccc1)OC[C@H]1CO1
• Canonical SMILES: O1C[C@@H]1COC(c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C22H20O2/c1-4-10-18(11-5-1)22(24-17-21-16-23-21,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-15,21H,16-17H2/t21-/m1/s1
• InChIKey: XFSXUCMYFWZRAF-OAQYLSRUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(triphenylmethoxy)methyl]oxirane
• IUPAC Traditional name: (2R)-2-[(triphenylmethoxy)methyl]oxirane
• Synonyms: (R)-(+)-Glycidyl trityl ether; 三苯甲基-(R)-缩水甘油醚

Database IDs

• CAS Number: 65291-30-7
• MDL Number: MFCD00273368
• PubChem SID: 24868810; 162245121
• PubChem CID: 2734442

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.1227713
• LogD (pH = 7.4): 5.1227713
• Log P: 5.1227713
• Molar Refractivity: 96.8074 cm^3
• Polarizability: 37.57349 Å^3
• Polar Surface Area: 21.76 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 99-102 °C(lit.)
• Optical Rotation: [α]20/D +10.5°, c = 1 in chloroform

Safety Information

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

Product Information

• Purity: 98%
• Optical Purity: ee: 98% (GLC)
• Empirical Formula (Hill Notation): C22H20O2

DETAILS

Sigma Aldrich - 453455

Packaging
5 g in glass bottle
Application
Nucleotides with activity against herpes simplex virus 1 and 2, lipid ammonium salts, and thio analogs of phospholipids have been prepared recently through ring-opening of this epoxide with cytosine derivatives,1 amines,2 and thiols,3 respectively.