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CAS RN: 93379-48-7 | Product Number: B1614
(-)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane
![Thumbnail of (-)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane](/medias/B1614.jpg?context=bWFzdGVyfHJvb3R8MjAxMTZ8aW1hZ2UvanBlZ3xhRGN6TDJnNE1DODRPVE16TXpjeU1qWTBORGM0TDBJeE5qRTBMbXB3Wnd8OTkyMjM4ZDFkNWIzZmM3MjUzNzc4YTZmMWE4ZGU5MDYwMDg2MDc4OGRhZDJlZDg2OWJjOGI1Y2I1NWNkM2M3ZA "(-)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane")
![Chemical Structure of (-)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane](/medias/B1614.jpg?context=bWFzdGVyfHJvb3R8NzA2MDB8aW1hZ2UvanBlZ3xhRGxsTDJoa1pTODRPVEU1T1RVNU5EY3dNVEV3TDBJeE5qRTBMbXB3Wnd8YWY1YzA2ZWEwZjFkMDI1Y2Y1ZDg1MGUyOWQwYTI4OGFiYTBkYTYxNTgyNzM0NjA2MTA0OWM2ZGJhMDBkZDg1Zg "(-)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane")
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![(-)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane](/_ui/responsive/theme-tci/images/missing_product_zoom.webp "(-)-4,5-Bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane")
Purity: >97.0%(HPLC)
Synonyms:
- (-)-trans-α,α'-(2,2-Dimethyl-1,3-dioxolane-4,5-diyl)bis(diphenylmethanol)
- (2R,3R)-2,3-O-Isopropylidene-1,1,4,4-tetraphenyl-1,2,3,4-butanetetrol
- (-)-2,3-O-Isopropylidene-1,1,4,4-tetraphenyl-L-threitol
- TADDOL
Product Documents:
| Size | Unit Price | Belgium | Japan* | Quantity |
Shipping Information
|
|---|---|---|---|---|---|
| 1G |
26,00 €
|
2 | 16 |
|
|
| 5G |
94,00 €
|
1 | 18 |
|
* Stock available in Belgium: Shipment on the same day
* Stock available in Japan: Please check the Shipping Simulation for estimated shipments. (excludes regulated items and dry ice shipments)
| Product Number | B1614 |
Purity / Analysis Method 
|
>97.0%(HPLC) |
| Molecular Formula / Molecular Weight | C__3__1H__3__0O__4 = 466.58 |
| Physical State (20 deg.C) | Solid |
| Storage Temperature
|
Room Temperature (Recommended in a cool and dark place, <15°C) |
| Packaging and Container
|
1G-Glass Bottle with Plastic Insert (View image) |
| CAS RN | 93379-48-7 |
| Reaxys Registry Number | 3657855 |
| PubChem Substance ID | 87564515 |
| MDL Number | MFCD00064467 |
Specifications
| Appearance | White to Almost white powder to crystal |
| Purity(HPLC) | min. 97.0 area% |
| Optical purity(LC) | min. 98.0 ee% |
| Melting point | 194.0 to 198.0 °C |
| NMR | confirm to structure |
Properties (reference)
| Melting Point | 196 °C |
| Specific Rotation | -69° (C=1,CHCl3) |
GHS
Related Laws:
Transport Information:
| HS Number | 2932990090 |
Application
Synthesis of Enantioenriched Axially Chiral Olefins via Asymmetric Wittig Reaction
Typical Procedure:
In a vial, (-)-4,5-bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane 4 g (14.0 mg, 0.030 mmol, 20 mol%) and a ketone (0.45 mmol, 3 eq.) are dissolved in toluene (0.75 mL). To the resulting solution, cooled to 0 °C, tert-butyl 2-[tris(4-methoxyphenyl)phosphoranylidene]acetate (70 mg, 0.15 mmol) is added in one portion. The vial is carefully capped, and the reaction mixture is left standing in an ice bath in a fridge (0 °C) without stirring and without precautions to exclude moisture or air. After 144 h, the product is directly obtained by chromatography on silica gel (n-hexane/Et2O 97.5 : 2.5, then 95 : 5).
In a vial, (-)-4,5-bis[hydroxy(diphenyl)methyl]-2,2-dimethyl-1,3-dioxolane 4 g (14.0 mg, 0.030 mmol, 20 mol%) and a ketone (0.45 mmol, 3 eq.) are dissolved in toluene (0.75 mL). To the resulting solution, cooled to 0 °C, tert-butyl 2-[tris(4-methoxyphenyl)phosphoranylidene]acetate (70 mg, 0.15 mmol) is added in one portion. The vial is carefully capped, and the reaction mixture is left standing in an ice bath in a fridge (0 °C) without stirring and without precautions to exclude moisture or air. After 144 h, the product is directly obtained by chromatography on silica gel (n-hexane/Et2O 97.5 : 2.5, then 95 : 5).
References
PubMed Literature
Product Articles
[TCIMAIL No.105] Chiral Ligands[Research Articles] Synthesis of Enantioenriched Axially Chiral Olefins via Asymmetric Wittig Reaction
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