(S,S)-Taddol
((4S,5S) · 97.0%(LC) · (+)-TADDOL · (S,S)-taddol · SEEBACH REAGENT · bis(diphenylmethanol) · (4S,5S)-2,2-Dimethyl-α · (+)-4,5-Bis[hydroxy(diphenyL
Identifikatoren & physikalische Daten
| CAS No. | 93379-49-8 |
|---|---|
| Summenformel | C31H30O4 |
| Durchschnittliche Molmasse | 466,6 g/mol |
| Monoisotopische Masse | 466,21440944 g/mol |
| SMILES | CC1(C)O[C@H](C(O)(c2ccccc2)c2ccccc2)[C@@H](C(O)(c2ccccc2)c2ccccc2)O1 |
| InChIKey | OWVIRVJQDVCGQX-NSOVKSMOSA-N |
| PubChem CID | 9852051 |
| DTXSID | DTXSID701317964 |
Chemische & physikalische Eigenschaften
| XLogP | 5,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 58,9 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 35 |
| Formalladung | 0 |
| Komplexität | 573 |
| Schmelzpunkt | 193-196 °C(lit.) |
| Siedepunkt | 633.2±50.0 °C(Predicted) |
| Dichte | 1.200±0.06 g/cm3(Predicted) |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Aggregatzustand | powder to crystal |
| pKa (Säurekonstante) | 12.28±0.29(Predicted) |
| Farbe | White to Almost white |
| BRN | 4724097 |
| InChIKey | RNSJHECWLNVNFE-LOYHVIPDSA-N |
| SMILES | C(O)(C1C=CC=CC=1)(C1C=CC=CC=1)[C@H]1OC(C)(C)O[C@@H]1C(O)(C1C=CC=CC=1)C1C=CC=CC=1 |&1:14,20,r| |
| CAS Datenbank | 93379-49-8(CAS DataBase Reference) |
Sicherheit & Vorschriften
| Regulatorische Informationen | 1,3-Dioxolane-4,5-dimethanol, 2,2-dimethyl-.alpha.,.alpha.,.alpha.',.alpha.'-tetraphenyl-, (4S,5S)-: Does not have an individual approval but may be used under an appropriate group standard |
|---|---|
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29329990 |
| R-Sätze (R) | 20/21/22-36/37/38 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 26-36 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Verwenden
Ligand for enantioselective Lewis-acid mediated Diels-Alder, allyltitanation of aldehydes, and Michael-Mukaiyama additions promoted by chiral Ti-complexes.
Herstellung & Synthese
synthetische
Preparative Methods of (4R,5R)-2,2-Dimethyl-4,5-bis(hydroxydiphenylmethyl)-1,3-dioxolane: chiral titanates are usually prepared by mixing dichlorodiisopropoxytitanium and a chiral 1,4-diol in toluene. Other solvents such as ether and dichloromethane can also be employed. The alcohol exchange reaction takes place immediately at rt. Wherever necessary, liberated isopropyl alcohol is removed by azeotropic removal with toluene. The chiral 1,4-diols are prepared from dimethyl (or diethyl) tartrate by a two-step procedure comprising acetalization followed by the addition of an aryl Grignard reagent.