(5R)-5-[(triphenylmethoxy)methyl]oxolan-2-one

• ChemBase ID: 149591
• Molecular Formular: C24H22O3
• Molecular Mass: 358.42968
• Monoisotopic Mass: 358.15689456
• SMILES: c1ccc(cc1)C(c1ccccc1)(c1ccccc1)OC[C@H]1CCC(=O)O1
• Canonical SMILES: O=C1CC[C@@H](O1)COC(c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C24H22O3/c25-23-17-16-22(27-23)18-26-24(19-10-4-1-5-11-19,20-12-6-2-7-13-20)21-14-8-3-9-15-21/h1-15,22H,16-18H2/t22-/m1/s1
• InChIKey: OZWWLABCDGFABG-JOCHJYFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-5-[(triphenylmethoxy)methyl]oxolan-2-one
• IUPAC Traditional name: (5R)-5-[(triphenylmethoxy)methyl]oxolan-2-one
• Synonyms: 5-O-Trityl-2,3-dideoxy-L-glyceropentono-1,4-lactone; (R)-(-)-Dihydro-5-trityloxymethyl-2(3H)-furanone; (R)-(-)-γ-Trityloxymethyl-γ-butyrolactone; (R)-(-)-二氢-5-三苯甲基甲氧基-2(3H)-呋喃酮; (R)-(-)-γ-三苯甲基甲氧基-γ-丁内酯

Database IDs

• CAS Number: 78158-90-4
• MDL Number: MFCD00043001
• Beilstein Number: 4911276
• PubChem SID: 24889892; 24867486; 162243754
• PubChem CID: 12869482

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.319298
• LogD (pH = 7.4): 5.319298
• Log P: 5.319298
• Molar Refractivity: 106.072 cm^3
• Polarizability: 41.299053 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 150-152 °C; 150-152 °C(lit.)
• Optical Rotation: [α]20/D -26±1°, c = 1% in methylene chloride; [α]20/D -26°, c = 1 in methylene chloride

Safety Information

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

Product Information

• Purity: ≥95.0% (CH); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C24H22O3

DETAILS

Sigma Aldrich - 438979

Packaging
1 g in glass bottle
Application
This compound was used in the synthesis of target pentonolactones for interaction studies of γ-lactones with the phorbol ester receptor of protein kinase1