Description

(3S,5S)-3,5-Bis(tert-Butyldimethylsilyloxy)-2-Methylene-Cyclohexanone is a high-purity, chiral synthetic intermediate featuring a protected diol and an exocyclic methylene ketone. This compound matters for its role as a critical building block in the stereoselective synthesis of complex natural products and active pharmaceutical ingredients (APIs). Pharmaceutical, agrochemical, and advanced material research laboratories need this reagent for constructing intricate molecular architectures with precise stereochemical control.

Application

• Pharmaceutical Intermediate: A key chiral precursor in the synthesis of steroid analogs, prostaglandins, and other bioactive molecules requiring defined (3S,5S) stereochemistry.
• Asymmetric Synthesis: Serves as a versatile substrate for nucleophilic additions, cycloadditions, and other transformations to create new chiral centers.
• Natural Product Synthesis: Used in the construction of complex polycyclic frameworks found in terpenoids and other natural compounds.
• Agrochemical Research: Employed in developing chiral active ingredients for herbicides and fungicides.
• Material Science: Potential monomer or precursor for chiral polymers and advanced organic materials.
• Process Chemistry & Scale-up: Suitable for development into a registered starting material (RSM) for GMP manufacturing campaigns.

Basic Information

Product Name	(3S,5S)-3,5-Bis(tert-Butyldimethylsilyloxy)-2-Methylene-Cyclohexanone
CAS No.	190062-19-2
Molecular Formula	C19H38O3Si2
Molecular Weight	370.68 g/mol
Synonyms	(3S,5S)-3,5-Bis[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexanone; (3S,5S)-3,5-Bis-O-(tert-butyldimethylsilyl)-2-methylidenecyclohexanone; (3S,5S)-3,5-Bis[(tert-butyldimethylsilyl)oxy]-2-methylidenecyclohexanone; 2-Methylene-(3S,5S)-bis(tert-butyldimethylsiloxy)cyclohexanone; (3S-cis)-3,5-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexanone; TBS-protected (3S,5S)-2-Methylenecyclohexane-1,3-diol ketone
EINECS	Contact for details

Quality Control

Every batch of (3S,5S)-3,5-Bis(tert-Butyldimethylsilyloxy)-2-Methylene-Cyclohexanone is produced and tested under strict quality management systems. We ensure compliance with relevant industry standards for fine chemical intermediates. Comprehensive analytical testing, including chiral purity verification, is performed. Certificates of Analysis (COA) detailing identity, purity, and impurity profiles are provided with each shipment to guarantee batch-to-batch consistency and support your regulatory filings.

Storage

Preserve in a tightly closed container, protected from light. Store in a cool, dry place at 15-25°C. This compound is hygroscopic (moisture-sensitive) and light-sensitive; therefore, containers must be kept tightly sealed under an inert atmosphere (e.g., nitrogen or argon) and in original packaging to minimize exposure to moisture and light. Keep away from heat and incompatible materials.

Specification

Item	Specification
Appearance	White to off-white crystalline solid or powder
Identification (IR)	Conforms to structure
Identification (HPLC)	Retention time matches reference standard
Assay (HPLC)	≥97.0%
Chiral Purity (Chiral HPLC)	≥98.0% de (diastereomeric excess)
Water Content (KF)	≤0.5%
Residue on Ignition	≤0.1%
Heavy Metals	≤20 ppm

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