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CAS RN: 112022-81-8 | Product Number: D2131
(S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine
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Purity: >98.0%(T)
Synonyms:
- (S)-3,3-Diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole
- (S)-Me-CBS Catalyst
- (S)-(-)-2-Methyl-CBS-oxazaborolidine
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| Product Number | D2131 |
Purity / Analysis Method 
|
>98.0%(T) |
| Molecular Formula / Molecular Weight | C__1__8H__2__0BNO = 277.17 |
| Physical State (20 deg.C) | Solid |
| Storage Temperature
|
Frozen (<0°C) |
| Store Under Inert Gas | Store under inert gas |
| Condition to Avoid | Moisture Sensitive,Heat Sensitive |
| CAS RN | 112022-81-8 |
| Reaxys Registry Number | 8492123 |
| PubChem Substance ID | 87568575 |
| MDL Number | MFCD00078439 |
Specifications
| Appearance | White to Almost white powder to crystal |
| Purity(GC) | min. 95.0 % |
| Purity(Nonaqueous Titration) | min. 98.0 % |
| Specific rotation [a]20/D | -66.0 to -73.0 deg(C=1, MeOH) |
| NMR | confirm to structure |
Properties (reference)
| Specific Rotation | -68° (C=1,MeOH) |
| Solubility (slightly sol. in) | Methanol |
GHS
Related Laws:
Transport Information:
| H.S.code* | 2934.99-000 |
Application
Corey-Bakshi-Shibata Reduction (CBS Reduction)
Typical Procedure:
A freshly prepared solution of 0.5 M dimethyl sulfide borane in toluene (48 µL, 0.024 mmol) is added to a solution of 1 (4.5 mg, 0.012 mmol) and 0.05 M (S)-Me-CBS catalyst in toluene (470 µL, 0.024 mmol) at -78 °C under N2 atmosphere. After the mixture is stirred for 15 h at -30 ℃, methanol (100 µL) is added, followed by water (0.5 mL) and Et2O (2 mL), and the mixture is warmed to 23 ℃. Water (10 mL) and Et2O (10 mL) are added, and the aqueous portion is extracted with Et2O (2 x 20 mL). The combined organic fractions are dried (MgSO4) and concentrated in vacuo. Flash chromatography (SiO2, Et2O : hexane = 8 : 92) affords 2 (4.1 mg, 91% yield) as a clear oil.
A freshly prepared solution of 0.5 M dimethyl sulfide borane in toluene (48 µL, 0.024 mmol) is added to a solution of 1 (4.5 mg, 0.012 mmol) and 0.05 M (S)-Me-CBS catalyst in toluene (470 µL, 0.024 mmol) at -78 °C under N2 atmosphere. After the mixture is stirred for 15 h at -30 ℃, methanol (100 µL) is added, followed by water (0.5 mL) and Et2O (2 mL), and the mixture is warmed to 23 ℃. Water (10 mL) and Et2O (10 mL) are added, and the aqueous portion is extracted with Et2O (2 x 20 mL). The combined organic fractions are dried (MgSO4) and concentrated in vacuo. Flash chromatography (SiO2, Et2O : hexane = 8 : 92) affords 2 (4.1 mg, 91% yield) as a clear oil.
References
- Total Synthesis of Dysidiolide
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Related Products
(S)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine (ca. 1mol/L in Toluene)
| Product # | D5912 |
| CAS RN | 112022-81-8 |
| Purity / Analysis Method: |