133261-83-3

Basic information

• Product Name: (R)-2-METHYL-CBS-OXAZABOROLIDINE
• Synonyms: ALPHA,ALPHA-DIPHENYL-D-PROLINOL METHYLBORONIC ACID CYCL-AMIDE-ESTER;(R)-TETRAHYDRO-1-METHYL-3,3-DIPHENYL-1H,3H-PYRROLO[1,2-C][1,3,2] OXAZABOROLE;(R)-TETRAHYDRO-1-METHYL-3,3-DIPHENYL-1H,3H-PYRROLO[1,2-C][1,3,2]OXAZOBOROLE;(R)-METHYL OXAZABOROLIDINE;(R)-ME CBS;(R)-2-METHYL-CBS-OXAZABOROLIDINE MONOHYDRATE;(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
• CAS NO: 133261-83-3
• Molecular Formula: C18H20BNO
• Molecular Weight: 277.17
• Mol File: 133261-83-3.mol
• Article Data: 23

Chemical Properties

• Melting Point: 85-95 °C(lit.)
• Boiling Point: 111 °C
• Flash Point: 40 °F
• Appearance: /
• Density: 0.95 g/mL at 25 °C
• Storage Temp.: 2-8°C
• PKA: 1.02±0.40(Predicted)
• CAS DataBase Reference: (R)-2-METHYL-CBS-OXAZABOROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-METHYL-CBS-OXAZABOROLIDINE(133261-83-3)
• EPA Substance Registry System: (R)-2-METHYL-CBS-OXAZABOROLIDINE(133261-83-3)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-38-48/20-63-65-67
• Safety Statements: 36/37-62
• RIDADR: UN 1294 3/PG 2
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 133261-83-3(Hazardous Substances Data)

Usage

General Description

(R)-2-METHYL-CBS-OXAZABOROLIDINE is a chiral catalyst used in organic chemistry for asymmetric transformations. It is a boron-containing compound that has been shown to be effective in promoting a range of stereoselective reactions, such as asymmetric reductions and alkylations. The (R)-2-METHYL-CBS-OXAZABOROLIDINE has found applications in the synthesis of pharmaceuticals and agrochemicals, as well as in the development of new materials. Its unique structure and reactivity make it a valuable tool for the creation of complex, chiral molecules with high enantioselectivity.

Upstream product

• 22348-32-9 (S)-diphenylprolinol 
• 13061-96-6 dihydroxy-methyl-borane 
• 7318-81-2 bis(methoxy)methylborane 
• 22348-32-9 (R)-α,α-diphenylprolinol 
• 823-96-1 Trimethylboroxine 
• 151293-60-6 methylbis(diisopropylamino)borane 
• 86595-28-0 methyldi-n-butoxyborane 

Downstream Products

• 391906-07-3 (1R)-2-bromo-1-(3-pyridinyl)-1-ethanol 
• 52780-14-0 (R)-1-(3-bromophenyl)ethanol 
• 76116-24-0 (R)-1-(3-nitrophenyl)ethanol 
• 530084-79-8 8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one 
• 202530-97-0 (R)-2-pentyl-2-cyclopentenol 
• 174060-40-3 3-[(2R)-oxiranyl]pyridine 
• 357405-40-4 (S)-α-(2-Chloroethyl)-5-isoxazolemethanol 
• 1354227-36-3 C₁₀H₂₁NO₃ 

Relevant articles and documents

Efficient synthesis of (R)-phenylephrine using a polymer-supported Corey-Bakshi-Shibata catalyst

An efficient and mild synthetic route to (R)-phenylephrine hydrochloride using Corey-Bakshi-Shibata (CBS) catalyst was reported. In order to avoid a lengthy recovery process of the catalyst from homogeneous reaction, a polymer-supported CBS catalyst was prepared, and a preliminary attempt was made to achieve a continuous reduction on a laboratory scale, which contributes to synthesis of (R)-phenylephrine in a cost-effective way.

Chiral MeCBS synthesis process

The invention discloses a chiral MeCBS synthesis process. The process comprises the steps of adding 1.1-1.5 equivalent weight of methyl-boric acid in alkane solvent for back flow and water division, after the reaction is complete, lowering the temperature to 30-45 DEG C, after keeping static for filtration, lowering the filtered solution to below -20-0 DEG C, stirring and leaching out, after filtration and drying, acquiring the chiral MeCBS which is white solid with good fluidity. The processing method has the advantages of being simple in operation, being high in product purity, thus providing more choices in the current market with more available solvent types.

Enantioselective catalytic desymmetrization of maleimides by temporary removal of an internal mirror plane and stereoablative over-reduction: Synthesis of (R)-pyrrolam A

A highly enantioselective (>95% ee) strategy to affect the desymmetrization of a maleimide has been performed by temporary attachment to an anthracene template followed by asymmetric reduction with an oxazaborolidine catalyst. A stereoablative over-reduction process was partially responsible for the high levels of enantioselectivity. Exemplification of the strategy by stereoselective functionalization and retro-Diels-Alder reaction provided the natural product pyrrolam A.