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

• ChemBase ID: 146837
• Molecular Formular: C12H18O6
• Molecular Mass: 258.26772
• Monoisotopic Mass: 258.1103383
• SMILES: CC1(OC[C@]2(O1)C(=O)[C@H]1[C@@H](CO2)OC(O1)(C)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+/m1/s1
• InChIKey: IVWWFWFVSWOTLP-RWYTXXIDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,6S,7aR)-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: (3aR,6S,7aR)-2,2,5',5'-tetramethyl-dihydro-3aH-spiro[[1,3]dioxolo[4,5-c]pyran-6,2'-[1,4]dioxolane]-7-one
• Synonyms: Shi’s epoxidation catalyst; 1,2:4,5-Di-O-isopropylidene-β-D-erythro-2,3-hexodiulo-2,6-pyranose; Shi Epoxidation Diketal Catalyst; 1,2:4,5-Di-O-isopropylidene-beta-D-erythro-2,3-hexodiulo-2,6-pyranose; D-Epoxone; 1,2:4,5-二-O-异亚丙基-β-D-赤式-2,3-二酮-2,6-吡喃糖; D-1,2:4,5-二邻异丙二烯-B-D-红-2,-己基; D-1,2:4,5-二邻异丙二烯-B-D-红-2,3-己基

Database IDs

• CAS Number: 18422-53-2
• EC Number: 000-000-0
• MDL Number: MFCD11865369; MFCD00063383
• Beilstein Number: 1319073
• PubChem SID: 162241029; 24874093
• PubChem CID: 7275400

CALCULATED PROPERTIES

• 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
• Polarizability: 24.3432 Å^3
• Polar Surface Area: 63.22 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 101-103°C; 102-104 °C(lit.)
• Optical Rotation: [α]20/D -120.9°, c = 1 in chloroform

Safety Information

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

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C12H18O6

DETAILS

Sigma Aldrich - 520160

Application
This organocatalyst is able to epoxidize trans alkenes and certain cis alkenes with good to excellent yields and selectivities.1,2,3,4,5
Packaging
5 g in glass bottle

REFERENCES

• Developed by Shi's group for the enantioselective epoxidation of alkenes. Used in substoichiometric amounts in the presence of Oxone^TM or hydrogen peroxide, a chiral dioxirane is formed which converts trans-disubstituted and trisubstituted alkenes to epoxides with high ee: J. Am. Chem. Soc., 119, 11224 (1997); Tetrahedron Lett., 40, 8721 (1999). Selective monoepoxidation of dienes: J. Org. Chem., 63, 2948 (1998), or enynes: Tetrahedron Lett., 39, 4425 (1998), can be achieved. Has also been applied to the kinetic resolution of racemic cyclic olefins: J. Am. Chem. Soc., 121, 7718 (1999).