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CAS RN: 112022-83-0 | Product Number: D2130
(R)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine
Purity: >97.0%(T)
Synonyms:
- (R)-3,3-Diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole
- (R)-Me-CBS Catalyst
- (R)-(+)-2-Methyl-CBS-oxazaborolidine
Documents:
Size | Unit Price | Belgium | Japan* | Quantity |
---|---|---|---|---|
1G |
€42.00
|
Contact Us | Contact Us |
|
5G |
€126.00
|
Contact Us | Contact Us |
|
*Stock available in Belgium will be delivered in 1 to 3 days
*Stock available in Japan will be delivered in 1 to 2 weeks (excludes regulated items and dry ice shipments).
Product Number | D2130 |
Purity / Analysis Method | >97.0%(T) |
Molecular Formula / Molecular Weight | C__1__8H__2__0BNO = 277.17 |
Physical State (20 deg.C) | Solid |
Storage Temperature | 0-10°C |
Store Under Inert Gas | Store under inert gas |
Condition to Avoid | Moisture Sensitive,Heat Sensitive |
CAS RN | 112022-83-0 |
Reaxys Registry Number | 9059874 |
PubChem Substance ID | 87568574 |
MDL Number | MFCD00078440 |
Specifications
Appearance | White to Almost white powder to crystal |
Purity(Nonaqueous Titration) | min. 97.0 % |
Specific rotation [a]20/D | +66.0 to +73.0 deg(C=1, MeOH) |
Properties (reference)
Specific Rotation | 68° (C=1,MeOH) |
GHS
Related Laws:
Transport Information:
HS Number | 2934999090 |
Application
Asymmetric Reduction Using CBS Catalyst
Experimental procedure5): To a solution of 1 (3.52 g, 10.8 mmol) in toluene (85 mL) is added (R)-CBS-Me catalyst (1 mol/L in toluene, 4.30 mL, 4.30 mmol) and the solution is cooled to -78 °C. A solution of catecholborane (3.44 mL, 32.3 mmol) in toluene (20 mL) is added dropwise over 30 minutes. After stirring for 6 hours at -78 °C, water (40 mL) is added and the reaction is allowed to warm to rt. The reaction mixture is poured on water (150 mL) and extracted with Et2O (3 x 125 mL). The combined organic layers are washed with 1 mol/L NaOH (2 x 100 mL), saturated NaCl (100 mL), dried over MgSO4, and concentrated under vacuum. The crude product is purified by flash chromatography (hexanes:EtOAc = 4:1) to provide 3.00 g (85% yield, 98% ee) of 2 as a clear oil.
References
- 1)Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines. Mechanism and synthetic implications
- 2)A stable and easily prepared catalyst for the enantioselective reduction of ketones. Applications to multistep syntheses
- 3)Enantioselective route to a key intermediate in the total synthesis of ginkgolide B
- 4)Total synthesis of (±)-forskolin
- 5)Total Synthesis of (+)-Lyconadin A and Related Compounds via Oxidative C-N Bond Formation
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