(3aS,6R,7aS)-2,2,5',5'-tetramethyl-tetrahydro-2H-spiro[[1,3]dioxolo[4,5-c]pyran-6,2'-[1,4]dioxolane]-7-one

• ChemBase ID: 90766
• Molecular Formular: C12H18O6
• Molecular Mass: 258.26772
• Monoisotopic Mass: 258.1103383
• SMILES: O1C(OC[C@@]21C(=O)[C@@H]1[C@@H](OC(O1)(C)C)CO2)(C)C
• Canonical SMILES: O=C1[C@H]2OC(O[C@H]2CO[C@]21COC(O2)(C)C)(C)C
• InChI: InChI=1S/C12H18O6/c1-10(2)15-6-12(18-10)9(13)8-7(5-14-12)16-11(3,4)17-8/h7-8H,5-6H2,1-4H3/t7-,8-,12+/m0/s1
• InChIKey: IVWWFWFVSWOTLP-YVZVNANGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aS,6R,7aS)-2,2,5',5'-tetramethyl-tetrahydro-2H-spiro[[1,3]dioxolo[4,5-c]pyran-6,2'-[1,4]dioxolane]-7-one
• IUPAC Traditional name: (3aS,6R,7aS)-2,2,5',5'-tetramethyl-dihydro-3aH-spiro[[1,3]dioxolo[4,5-c]pyran-6,2'-[1,4]dioxolane]-7-one
• Synonyms: Shi epoxidation catalyst; L-enantiomer; 1,2:4,5-Bis-O-(isopropylidene)-beta-L-erythro-2,3-hexodiulo-2,6-pyranose; Shi epoxidation catalyst enantiomer; 1,2:4,5-Bis-O-(isopropylidene)-β-L-erythro-2,3-hexodiulo-2,6-pyranose; 史氏环氧化反应催化剂对映体; 1,2:4,5-双-O-(异亚丙基)-β-L-赤式-2,3-二酮-2,6-吡喃糖

Database IDs

• CAS Number: 198965-05-8
• MDL Number: MFCD16621458
• PubChem SID: 162077497
• PubChem CID: 11391247

CALCULATED PROPERTIES

• Polarizability: 24.3432 Å^3
• Polar Surface Area: 63.22 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true
• Acid pKa: 15.104746
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 1.4142153
• LogD (pH = 7.4): 1.4142153
• Log P: 1.4142153
• Molar Refractivity: 60.0832 cm^3

PROPERTIES

Physical Property

• Melting Point: 98-104 °C; 98-104°C
• Optical Rotation: [α]22/D +111.0°, c = 0.5 in chloroform

Safety Information

• Storage Warning: Harmful
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302

Product Information

• Empirical Formula (Hill Notation): C12H18O6

DETAILS

Sigma Aldrich - 718653

Packaging
250 mg in glass bottle
Application
Reactant for:
• Diastereoselective synthesis of a-tocopherol via Shi epoxidation1
• Synthesis of benzimidazole-based analogs of epothilone A with anticancer activity2Catalyst for:
• Preparation of microtubule-stabilizing and antitumor active analogs of epothilone3
• Synthesis of (+)-aurilol via regio- and stereocontrolled A-D ether ring formations4