(Z)-[2-{(3R,4R,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylene-4-(3-(tert-butyldiphenylsilanyloxy)propoxy)cyclohexylidene}ethyl]diphenylphosphine oxide
[CAS# 1254276-84-0]

Identification

• Classification: Organic raw materials >> Organosilicon compound
• Name: (Z)-[2-{(3R,4R,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylene-4-(3-(tert-butyldiphenylsilanyloxy)propoxy)cyclohexylidene}ethyl]diphenylphosphine oxide
• Synonyms: Eldecalcitol Intermediate
• Molecular Formula: C₅₂H₇₅O₅PSi₃
• Molecular Weight: 895.38
• CAS Registry Number: 1254276-84-0
• SMILES: CC(C)(C)[Si](C)(C)O[C@@H]1C/C(=C/CP(=O)(C2=CC=CC=C2)C3=CC=CC=C3)/C(=C)[C@H]([C@@H]1OCCCO[Si](C4=CC=CC=C4)(C5=CC=CC=C5)C(C)(C)C)O[Si](C)(C)C(C)(C)C

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.545, Calc.^*
• Boiling Point: 776.4±60.0 °C (760 mmHg), Calc.^*
• Flash Point: 423.4±32.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06 Danger
• Risk Statements: H300
• Safety Statements: P264-P270-P301+P310+P330-P405-P501
• Transport Information: UN 2811

Discovery and Applications

(Z)-[2-{(3R,4R,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylene-4-(3-(tert-butyldiphenylsilanyloxy)propoxy)cyclohexylidene}ethyl]diphenylphosphine oxide is a highly specialized organophosphorus compound widely used in organic synthesis and materials science. This complex molecule incorporates multiple protective groups, including tert-butyldimethylsilyl (TBS) and tert-butyldiphenylsilyl (TBDPS) groups, which contribute to its stability and reactivity in targeted transformations.

The discovery of this compound emerged from research in organophosphorus chemistry and synthetic methodology aimed at developing novel reagents for asymmetric synthesis and catalysis. Its structure features a cyclohexylidene core with strategically placed silyl ether functionalities that facilitate selective transformations. The phosphine oxide moiety further enhances its utility in coordination chemistry and as a precursor for phosphine ligands in transition metal catalysis.

One of the key applications of this compound is in organocatalysis and transition metal-mediated reactions. The phosphine oxide functionality provides a platform for designing efficient ligands in asymmetric hydrogenation, cross-coupling, and other catalytic processes. The presence of silyl-protected hydroxyl groups allows for controlled deprotection, enabling the stepwise introduction of functional groups in complex molecule synthesis.

In pharmaceutical research, derivatives of this molecule have been investigated for their potential in drug development. Phosphine oxide-containing compounds play a crucial role in modifying biological activity and optimizing drug candidates for improved solubility and bioavailability. The unique steric and electronic properties of this structure make it a valuable intermediate in the synthesis of bioactive molecules targeting various therapeutic areas.

Another significant area of application is in materials science, where phosphine oxides contribute to the development of flame retardants, advanced polymers, and high-performance coatings. The combination of silyl-protected functionalities and a phosphine oxide core allows for the creation of materials with enhanced thermal stability and mechanical properties.

The synthesis of (Z)-[2-{(3R,4R,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-2-methylene-4-(3-(tert-butyldiphenylsilanyloxy)propoxy)cyclohexylidene}ethyl]diphenylphosphine oxide typically involves multi-step procedures incorporating selective protection, functionalization, and coupling reactions. Advances in synthetic strategies continue to refine the efficiency and scalability of its production, making it increasingly accessible for both research and industrial applications.

Safety considerations for handling this compound include standard precautions associated with organophosphorus and silyl ether-containing chemicals. Proper protective equipment and ventilation are recommended to minimize exposure risks. Storage under inert conditions prevents degradation and maintains the compound’s reactivity for laboratory and industrial use.

Future research on this molecule is expected to focus on its expanded role in catalysis, drug discovery, and materials science. The development of more sustainable and selective synthetic approaches will enhance its practical applications and contribute to the advancement of high-value chemical transformations.

References

2021. Synthesis of Eldecalcitol. Synfacts.
DOI: 10.1055/s-0040-1720324