4,5-dimethyl (4S,5S)-2-phenyl-1,3-dioxolane-4,5-dicarboxylate

• ChemBase ID: 136892
• Molecular Formular: C13H14O6
• Molecular Mass: 266.24666
• Monoisotopic Mass: 266.07903817
• SMILES: COC(=O)[C@@H]1[C@H](OC(O1)c1ccccc1)C(=O)OC
• Canonical SMILES: COC(=O)[C@H]1OC(O[C@@H]1C(=O)OC)c1ccccc1
• InChI: InChI=1S/C13H14O6/c1-16-11(14)9-10(12(15)17-2)19-13(18-9)8-6-4-3-5-7-8/h3-7,9-10,13H,1-2H3/t9-,10-/m0/s1
• InChIKey: FMSYNRGOFIGJMM-UWVGGRQHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4,5-dimethyl (4S,5S)-2-phenyl-1,3-dioxolane-4,5-dicarboxylate
• IUPAC Traditional name: 4,5-dimethyl (4S,5S)-2-phenyl-1,3-dioxolane-4,5-dicarboxylate
• Synonyms: Dimethyl (4S,5S)-2-phenyl-1,3-dioxolane-4,5-dicarboxylate; (4S,5S)-2-Phenyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester; (+)-Dimethyl 2,3-O-benzylidene-D-tartrate; (4S,5S)-2-Phenyl-1,3-dioxolane-4,5-dicarboxylic acid, dimethyl ester; Dimethyl 2,3-O-benzylidene-D-tartrate; 2,3-O-苄烯酒石酸二甲酯; (4S,5S)-2-苯基-1,3-二氧戊环-4,5-二羧酸二甲酯; 2,3-O-苄烯-酒石酸二甲酯

Database IDs

• CAS Number: 91326-83-9; 38270-70-1
• MDL Number: MFCD00010199
• Beilstein Number: 4704640
• PubChem SID: 24848182; 162231159
• PubChem CID: 719735

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.6280675
• LogD (pH = 7.4): 1.6280675
• Log P: 1.6280675
• Molar Refractivity: 62.6352 cm^3
• Polarizability: 25.50175 Å^3
• Polar Surface Area: 71.06 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 73-75 °C; 74-76 °C(lit.)
• Optical Rotation: [α]20/D +33±1°, c = 7% in benzene; [α]20/D +41.9°, c = 2 in ethanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (sum of enantiomers, GC); 99%
• Empirical Formula (Hill Notation): C13H14O6

DETAILS

Sigma Aldrich - 13476

Other Notes
Starting material for the synthesis of chiral building blocks1; Preparation of 2-O-benzyl-D-threitol and protected D-threose derivative2,3,4
Packaging
25 g in glass bottle