57711-50-9

Usage

Uses

3-O-tert-Butyldimethylsilyl Cholesterol is a protected derivative of Cholesterol (C432501).

Upstream product

• 18173-64-3 tert-butyldimethylsilanol 
• 57-88-5 cholesterol 
• 72726-45-5 tert-butyldimethylsilyl iodide 
• 594-19-4 tert.-butyl lithium 
• 142095-81-6 3β-mesityldimethylsilyloxy-5-cholestene 
• 765935-41-9 cholesterol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 72726-46-6 tert-butyl(dimethyl)(phenylseleno)silane 
• 2243-09-6 5α-cholestane-3,6-dione 
• 570-85-4 5α-cholestane-3β,6β-diol 
• 540527-34-2 (3S,8S,9S,10R,13R,14S,17R)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-1-((R)-6-methylheptan-2-yl)-1,2,3,4,8,9,10,11,12,13,14,15,16,17-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one 
• 156809-64-2 3β-<(t-butyldimethylsilyl)oxy>-5α-cholestane-6β-ol 

Downstream Products

• 57-88-5 cholesterol 
• 4351-55-7 cholesteryl formate 
• 604-35-3 Cholesteryl acetate 

Relevant academic research and scientific papers

Synthesis of (20S)-[7,7,21,21-2H4]-3β-(tert- butyldimethylsilanyloxy)-20-methyl-pregn-5-en-21-ol, a useful intermediate for the preparation of deuterated isotopomers of sterols

(20S)-[7,7,21,21-2H4]-3β-(tert- Butyldimethylsilanyloxy)-20-methyl-pregn-5-en-21-ol, an intermediate for the preparation of deuterated isotopomers of sterols to be used as standards for biomedical studies, was prepared by reduction with dichloroaluminum deuteride of ethyl (20S)-3β-(tert-butyldimethylsilanyloxy)-7-oxo-pregn-5-en-20-carboxylate. Using controlled experimental conditions, it has also been shown that the dichloroaluminum hydride reduction of a 7-keto steroid affords the corresponding 7β-hydroxy derivative in a highly stereoselective manner.

Structure-activity relationship studies of Niemann-Pick type C1-like 1 (NPC1L1) ligands identified by screening assay monitoring pharmacological chaperone effect

A number of hereditary diseases are caused by defective protein trafficking due to a folding defect resulting from point mutations in proteins. Ligands that bind to the folding intermediates of such mutant proteins and rescue their trafficking defects, known as pharmacological chaperones, have promise for the treatment of certain genetic diseases, including Fabry disease, cystic fibrosis, and Niemann-Pick disease type C. Here we show that this pharmacological chaperone effect can be used for ligand screening, that is, binding of candidate ligands can be detected by monitoring the ligand-mediated correction of a localization defect caused by artificially introduced point mutations of the protein of interest. Using this method, we discovered novel steroidal ligands of Niemann-Pick type C1-like 1 (NPC1L1), an intestinal cholesterol transporter that is the target of the cholesterol absorption inhibitor ezetimibe, and conducted structure-activity relationship studies. We also present data indicating that the binding site of the new ligands is distinct from both the N-terminal sterol-binding domain and the ezetimibe-binding site.

Chemical synthesis of 7α-hydroxycholest-4-en-3-one, a biomarker for irritable bowel syndrome and bile acid malabsorption

7α-Hydroxy-cholest-4-en-3-one is a biomarker for bile acid loss, irritable bowel syndrome, and other diseases associated with defective bile acid biosynthesis. Furthermore, 7α-hydroxy-cholest-4-en-3-one is the physiological substrate for cytochrome P450 8B1 (P450 8B1 or CYP8B1), the oxysterol 12α-hydroxylase enzyme implicated in obesity and cardiovascular health. We report the chemical synthesis of this physiologically important oxysterol beginning with cholesterol. The key feature of this synthesis involves a regioselective C3-allylic oxidation of a 3-desoxy-Δ4-7α-formate steroid precursor to form 7α-formyloxy-cholest-4-en-3-one, which was saponified to yield 7α-hydroxy-cholest-4-en-3-one.

HEXADECAHYDRO-1H-CYCLOPENTA[A]PHENANTHRENE DERIVATIVES USEFUL IN TREATING PAIN AND INFLAMMATION

wherein,R1, R2, R3, R4a, R4b and R5 are described herein, or a stereoisomer, enantiomer or tautomer thereof or mixtures thereof, or a pharmaceutically acceptable salt or solvate thereof, are described herein, as well as other compounds. These compounds are useful in treating inflammation and/or pain. Compositions comprising a compound of the invention are also disclosed, as are methods of using the compounds to treat inflammation and/or pain.

INDENE DERIVATIVES USEFUL IN TREATING PAIN AND INFLAMMATION

Compounds of formula (I) wherein, R1, R2, R3, R4a, R4b and R5 are described herein, or a stereoisomer, enantiomer or tautomer thereof or mixtures thereof, or a pharmaceutically acceptable salt or solv

A new reagent system for efficient silylation of alcohols: Silyl chloride-N-methylimidazole-iodine

It was found that reactions of alcohols with silyl chlorides in the presence of N-methylimidazole were significantly accelerated by the added iodine, and on this basis a general, and high yielding method for efficient silylation of primary, secondary, and

Iodine-promoted silylation of alcohols with silyl chlorides. Synthetic and mechanistic studies

An efficient silylating system for 1°, 2°, and 3° alcohols, consisting of a silyl chloride/N-methylimidazole/iodine, was developed. Synthetic and mechanistic aspects of this new reagent system, and particularly the role of iodine were investigated in detail using 1H NMR spectroscopy.

A Convenient Method for Protection and Deprotection of Alcohols and Phenols as Alkylsilyl Ethers Catalyzed by Iodine under Microwave Irradiation

Irradiation of alcohols or phenols with tert-butyldimethylsilyl chloride (TBDMSCl) or trimethylsilyl chloride (TMSCl) in presence of catalytic amount (20 mol%) of iodine in a microwave oven for 2 min gives the corresponding silyl ethers in excellent yield. Iodine in methanol deprotects the silyl ether into its parent alcohol or phenol under similar reaction conditions.

Preparation of formate esters from O-TBDMS/O-TES protected alcohols. A one-step conversion using the Vilsmeier-Haack complex POCl3/DMF

O-tert-Butyldimethylsilylated (O-TBDMS) or O-triethylsilylated (O-TES) alcohols were converted in one step to their corresponding formates under Vilsmeier-Haack conditions (POCl3/DMF). The scope and limitations of this novel reaction for interconverting alcohol protecting groups are described.

Efficient and chemoselective protection of alcohols and phenols with tert-butyldimethylchlorosilane (TBDMCS) under solvent-free conditions

Various types of primary and secondary alcohols and phenols can be converted efficiently to their corresponding TBDMS ethers using TBDMCS/imidazole under solvent-free conditions. Elimination of DMF, accompanied with an easy non-aqueous work-up and a high rate enhancement of the reaction are worthy to be mentioned for the presented method. The reactions show absolute chemoselectivity for the protection of primary in the presence of secondary alcohols.