CAS 112022-83-0

(R)-2-Methyl-CBS-oxazaborolidine

Description:

(R)-2-Methyl-CBS-oxazaborolidine is a chiral organoboron compound that serves as a catalyst in various asymmetric synthesis reactions, particularly in the formation of carbon-carbon bonds. This compound features a boron atom coordinated to an oxazaborolidine framework, which contributes to its unique reactivity and selectivity in catalysis. The presence of the methyl group at the 2-position enhances its steric and electronic properties, making it effective for enantioselective reactions. Its chiral nature allows it to preferentially favor the formation of one enantiomer over another, which is crucial in the synthesis of pharmaceuticals and other fine chemicals. The compound is typically used in reactions such as the reduction of ketones and aldehydes, where it can facilitate the formation of alcohols with high enantiomeric excess. Additionally, (R)-2-Methyl-CBS-oxazaborolidine is valued for its stability and ease of handling, making it a popular choice in synthetic organic chemistry. Its applications extend to various fields, including medicinal chemistry and materials science, where chirality plays a significant role in the properties and activities of the resulting compounds.

Formula: C₁₈H₂₀BNO

InChI: InChI=1S/C18H20BNO/c1-19-20-14-8-13-17(20)18(21-19,15-9-4-2-5-10-15)16-11-6-3-7-12-16/h2-7,9-12,17H,8,13-14H2,1H3/t17-/m1/s1

InChI key: InChIKey=VMKAFJQFKBASMU-QGZVFWFLSA-N

SMILES: CB1OC([C@@]2(N1CCC2)[H])(C3=CC=CC=C3)C4=CC=CC=C4

Synonyms:

• (3AR)-1-methyl-3,3-diphenyl-3a,4,5,6-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole
• (3aR)-1-methyl-3,3-diphenyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole
• (3aR)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole
• (R)-(+)-2-Methyl-CBS-oxazaborolindine
• (R)-1-Methyl,3,3-Diphenyl-TETRAHYDRO-PYRROLO(1,2-C)(1,3,2)oxazaborole
• (R)-1-Methyl-3,3-diphenylhexahydropyrrolo[1,2-c]-[1,3,2]oxazaborole
• (R)-3,3-Diphenyl-1-MethylTETRAHYDRO-1H,3H-PYRROLO[1,2-C][1,3,2]oxazaborole
• (R)-3,3-Diphenyl-1-MethylTETRAHYDRO-3H-PYRROLO-[1,2-C][1,3,2]oxazaborole
• (R)-3,3-Diphenyl-1-methylpyrrolidino[1,2-c]-1,3,2-oxazaborole
• (R)-5,5-Diphenyl-2-Methyl-3,4-PROPANO-1,3,2-oxazaborolidine
• (R)-Me-CBS
• (R)-Me-Corey-Bakshi-Shibata reagent
• (R)-Methyl oxazaborolidine
• (R)-Methyl-CBS
• (R)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole
• (R-Methyl-Corey-Bakshi-Shibata catalyst
• 1H,3H-Pyrrolo[1,2-c][1,3,2]oxazaborole, tetrahydro-1-methyl-3,3-diphenyl-, (3aR)-
• 1H,3H-Pyrrolo[1,2-c][1,3,2]oxazaborole, tetrahydro-1-methyl-3,3-diphenyl-, (R)-
• ALPHA,ALPHA-Diphenyl-D-PROLINOL METHYLBORONIC ACID CYCL-AMIDE-ESTER

(R)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine (ca. 1mol/L in Toluene)

CAS: 112022-83-0

Formula: C₁₈H₂₀BNO

Color and Shape: Colorless to Light yellow clear liquid

Molecular weight: 277.17

Ref: 3B-D5911

(R)-2-Methyl-CBS-oxazaborolidine, 1M soln. in toluene

CAS: 112022-83-0

(R)-2-Methyl-CBS-oxazaborolidine is used in the asymmetric reduction of prochiral ketones. Other applications include the enantioselective synthesis of -hydroxy acids, -amino acids, C2 symmetrical ferrocenyl diols, and propargyl alcohols. It is also used in a desymmetrizing reduction leading to (S)-

Formula: C₁₈H₂₀BNO

Color and Shape: Clear colorless to pale yellow, Liquid

Molecular weight: 277.17

Ref: 02-L14582

CALLERY™ (R)-Methyl oxazaborolidine, 1M in toluene

CAS: 112022-83-0

(R)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole, 0.9-1.1M in toluene [(R)-Methyloxazaborolidine] (R)-CBS Catalyst

Formula: C₁₈H₂₀BNO

Color and Shape: colorless to amber liq.

Molecular weight: 277.17

Ref: 08-05-1000

(R)-1-methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole

CAS: 112022-83-0

Formula: C₁₈H₂₀BNO

Purity: 98%

Color and Shape: Solid

Molecular weight: 277.1685

Ref: IN-DA00327K

(R)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole

CAS: 112022-83-0

(R)-Tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole

Formula: C₁₈H₂₀BNO

Purity: 97%,99.5%ee

Color and Shape: brown liquid

Molecular weight: 277.17g/mol

Ref: 54-OR360007

(R)-5,5-Diphenyl-2-methyl-3,4-propano-1,3,2-oxazaborolidine

CAS: 112022-83-0

Formula: C₁₈H₂₀BNO

Purity: >97.0%(T)

Color and Shape: White to Almost white powder to crystal

Molecular weight: 277.17

Ref: 3B-D2130

(R)-Methyl oxazaborolidine 1M in toluene

CAS: 112022-83-0

Purity: 95.0%

Color and Shape: Liquid, Clear

Molecular weight: 369.32000732421875

Ref: 10-F043435

(R)-(+)-2-Methyl-CBS-oxazaborolidine

CAS: 112022-83-0

(R)-(+)-2-Methyl-CBS-oxazaborolidine is a dpp-iv inhibitor that is a β-unsaturated ketone. It has been shown to inhibit the enzyme histone lysine demethylase, which may be involved in the regulation of bone mass. This compound also has a pharmacokinetic profile that is characterized by high oral bioavailability, low plasma protein binding, and rapid metabolism by liver enzymes. The reaction mechanism for this compound is based on the formation of an enolate carbanion. (R)-(+)-2-Methyl-CBS-oxazaborolidine can be synthesized with high stereoselectivity and yields from reactions with simple starting materials. This synthetic route also has a number of advantages over other methods: it does not require any protecting groups, it does not use toxic solvents such as dichloromethane or chloroform, and it can be performed in anhydrous conditions

Formula: C₁₈H₂₀BNO

Purity: Min. 95%

Color and Shape: Solid

Molecular weight: 277.17 g/mol

Ref: 3D-FM163707