(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
Identifiers & Physical Properties
| CAS No. | 93379-49-8 |
|---|---|
| Molecular formula | C31H30O4 |
| Average molar mass | 466.6 g/mol |
| Monoisotopic mass | 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 |
Chemical & Physical Properties
| XLogP | 5.2 |
|---|---|
| Topological polar surface area | 58.9 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 6 |
| Heavy atoms | 35 |
| Formal charge | 0 |
| Complexity | 573 |
| Melting point | 193-196 °C(lit.) |
| alpha | -62.6 º (c=1 in chloroform) |
| Boiling point | 633.2±50.0 °C(Predicted) |
| Density | 1.200±0.06 g/cm3(Predicted) |
| Storage conditions | Inert atmosphere,Room Temperature |
| Physical state | powder to crystal |
| pKa (acidity coefficient) | 12.28±0.29(Predicted) |
| Color | White to Almost white |
| optical activity | [α]19/D +67°, c = 1 in chloroform |
| 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 DataBase Reference | 93379-49-8(CAS DataBase Reference) |
| UNSPSC Code | 12352005 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H317-H319 |
| GHS precautionary statements | P280-P305+P351+P338 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Hazard symbols | Xn |
| Risk statements (R) | 20/21/22-36/37/38 |
| Safety statements (S) | 26-36 |
| Water hazard class (WGK) | 3 |
| Customs code | 29329990 |
| Storage class | 11 - Combustible Solids |
Safety & Regulations
| Regulatory information | 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 |
|---|---|
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 3 |
| Customs code | 29329990 |
| Risk statements (R) | 20/21/22-36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xn |
| Safety statements (S) | 26-36 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H317-H319 |
| GHS precautionary statements | P280-P305+P351+P338 |
Applications & Uses
Uses
Ligand for enantioselective Lewis-acid mediated Diels-Alder, allyltitanation of aldehydes, and Michael-Mukaiyama additions promoted by chiral Ti-complexes.
Preparation & Synthesis
Preparation
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.