Description

2-[(3R,5R)-3,5-Bis[[(1,1-Dimethylethyl)Dimethylsilyl]Oxy]-4-Methylenecyclohexylidene]Ethyl]Diphenylphosphine Oxide is a highly specialized chiral phosphine oxide derivative featuring dual tert-butyldimethylsilyl (TBDMS) protecting groups and an exocyclic methylene functionality — engineered for precision in asymmetric catalysis and complex molecule synthesis. Its structural rigidity and stereodefined silyloxy motifs confer exceptional ligand stability and selectivity under demanding reaction conditions, making it a critical enabler for high-yield, enantioselective transformations. This compound is primarily utilized by pharmaceutical R&D laboratories, fine chemical manufacturers, and academic research groups developing next-generation catalysts for C–C bond formation, allylic substitutions, and transition-metal-mediated cyclizations.

Application

• Chiral ligand precursor in palladium- and rhodium-catalyzed asymmetric allylic alkylation reactions
• Key intermediate in the synthesis of sterically tuned phosphine-based catalysts for enantioselective Heck couplings
• Building block for advanced chiral phosphine oxides used in asymmetric epoxidation and dihydroxylation systems
• Research reagent in medicinal chemistry for constructing conformationally restricted scaffolds with defined stereochemistry
• Substrate in silyl-protecting group studies targeting selective deprotection strategies in multistep syntheses
• Tool compound for investigating structure–activity relationships (SAR) in phosphine oxide–metal coordination chemistry

Basic Information

Product Name	2-[(3R,5R)-3,5-Bis[[(1,1-Dimethylethyl)Dimethylsilyl]Oxy]-4-Methylenecyclohexylidene]Ethyl]Diphenylphosphine Oxide
CAS No.	213250-64-7
Molecular Formula	C35H53O3PSi2
Molecular Weight	623.94 g/mol
Synonyms	(3R,5R)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-4-methylenecyclohexylideneacetic acid diphenylphosphine oxide; TBDMS-protected chiral phosphine oxide; 2-[(3R,5R)-3,5-Bis[TBDMS-oxy]-4-methylenecyclohexylidene]ethyl diphenylphosphine oxide; Diphenyl(2-[(3R,5R)-3,5-bis[(1,1-dimethylethyl)dimethylsilyl]oxy-4-methylenecyclohexylidene]ethyl)phosphine oxide; Chiral bis-silylated cyclohexylidene phosphine oxide; CAS 213250-64-7; Ph2P(O)CH2C(=CH2)C6H8(OTBDMS)2
EINECS	Not listed

Quality Control

Our products undergo rigorous quality testing to ensure compliance with industry standards. Certificates of Analysis (COA) are available upon request. All batches are verified for identity (IR, NMR), purity (HPLC ≥98.5%), stereochemical integrity (chiral HPLC), and absence of heavy metals (ICP-MS tested). Manufacturing adheres to ISO 9001-certified processes and follows Good Manufacturing Practice (GMP) principles for research-grade specialty chemicals.

Storage

Preserve in a tightly closed container, protected from light. Store at 15–25°C under inert atmosphere (argon or nitrogen) due to hygroscopic nature. Keep away from moisture sources and maintain low-humidity environment (≤30% RH). Avoid exposure to ambient air during handling.

Specification

Item	Specification
Appearance	White to off-white crystalline powder
Identity (IR)	Conforms to reference spectrum
Identity (NMR)	1H and 13C NMR consistent with structure
Assay (HPLC)	≥98.5%
Diastereomeric Purity (chiral HPLC)	≥99.0% de
Residual Solvents (GC)	Meets ICH Q3C Class 3 limits
Water Content (KF)	≤0.2% w/w
Heavy Metals (ICP-MS)	≤10 ppm total

Note: Specifications can be tailored. Please contact us for the detailed technical data sheet of a specific grade.