83067-20-3

Usage

Uses

Used in Pharmaceutical Industry:
5-(TERT-BUTYLDIMETHYLSILYLOXY)-1-PENTANOL is used as a reagent for the synthesis of chroman-4-one and chromone-based sirtuin 2 inhibitors, which possess antiproliferative properties in cancer cells. These inhibitors have the potential to be developed into effective cancer treatments.
Used in Polymer Synthesis:
5-(TERT-BUTYLDIMETHYLSILYLOXY)-1-PENTANOL is used as a reagent in the synthesis of well-defined monoand ditelechelic polyphosphazenes. These polymers have a wide range of applications, including in the medical, automotive, and aerospace industries, due to their unique properties such as flame retardancy, biocompatibility, and thermal stability.

InChI:InChI=1/C11H26O2Si/c1-11(2,3)14(4,5)13-10-8-6-7-9-12/h12H,6-10H2,1-5H3

Upstream product

• 410087-91-1 (1,1-dimethylethyl)dimethyl[5-(3-methyl-2-butenyloxy)pentyl]oxy silane 
• 121671-67-8 1-(tert-butyldiphenylsilanyloxy)-5-(tert-butyldimethylsilanyloxy)pentane 
• 126889-45-0 1-(tert-Butyl-dimethyl-silanyloxy)-5-(diethyl-isopropyl-silanyloxy)-pentane 

Downstream Products

• 125878-24-2 5-Benzyloxy-pentanoic acid 5-(tert-butyl-dimethyl-silanyloxy)-pentyl ester 
• 83084-58-6 5-((tert-butyldimethylsilyl)oxy)pentyl 4-methylbenzenesulfonate 
• 556795-90-5 4-[5-(tert-butyldimethylsilyloxy)pentyloxy]benzaldehyde 
• 206267-67-6 4-benzo[d]1,3-dioxolan-5-yl-6-phenyl-2-(5-(1,1,2,2-tetramethyl-1-silapropoxy)pentyloxy)pyridine 
• 918123-42-9 5-(tert-butyldimethylsilyloxy)pent-1-yl 5-(trifluoromethyl)-3-nitrobenzoate 
• 1186125-53-0 C₄₄H₆₁FN₄O₉S 
• 1191079-87-4 C₃₄H₄₆FN₃O₈ 
• 1186125-48-3 ethyl (S)-7-(tert-butyldimethylsiloxy)-2,2-difluoro-3-{N-[(R)-2-methoxy-1-phenylethyl]amino}heptanoate 
• 1310803-48-5 C₃₆H₄₈O₃Si₂ 

Relevant academic research and scientific papers

Deprotection of a silyl group with mesoporous silica

The triethylsilyl (TES) group of silyl ethers of several types is selectively and easily removed in the presence of a t-butyldimethylsilyl (TBDMS) group with a mesoporous silica MCM-41/MeOH heterogeneous system. Comparison of the efficiency was carried out among several solvents, and among such promoters as common zeolites and ion-exchange resins. Furthermore, FSM-16, another mesoporous silica, was examined for the possibility of recycling by re-calcination at 400°C after the reaction.

Deprotection of t-butyldimethylsilyl ethers promoted by cerium(IV) triflate

t-Butyldimetylsilyl ethers are mildly cleft by catalytic amounts of cerium(IV) triflate. Dependence from water amount was observed.

The prenyl group: A versatile hydroxy protecting group, removable chemoselectively under mild conditions

Iodine in dichloromethane (in the presence of 3? molecular sieves for acid-sensitive substrates) and 2,3-dichloro-5,6-dicyanoquinone (DDQ) in dichloromethane-water (9:1) are mild and efficient methods to cleave prenyl ethers. These reaction conditions are compatible with the presence of other protecting groups such as acetals, acetates, allyl, benzyl and TBDPS groups. Exposure of aryl prenyl ethers to iodine led to the formation of 3-iodo-2,2-dimethylchroman derivatives in acceptable yields via a tandem Friedel-Crafts/iodocyclization reactions. Facile one-step transformation of two iodinated dimethylchroman derivatives allowed the synthesis of natural flavanoids among them: zanthoxylol, an anti-sickling agent.

Selective deprotection of triethylsilyl group in the presence of t-butyldimethylsilyl group with MCM-41/MeOH heterogeneous system

Triethylsilyl (TES) group of silyl ethers of several types is selectively and easily removed in the presence of t-butyldimethylsilyl group (TBS) with a mesoporous silica MCM-41/MeOH heterogeneous system. Comparison of the efficiency was carried out among several solvents, and among such promoters as common zeolites and ion-exchange resins. Thieme Stuttgart.

Selective acceleration for deprotection of benzyl ethers with ti-HMS

Ti-HMS, a Ti-loaded hexagonal mesoporous silica, was found to accelerate deprotection of benzyl ethers under hydrogenolytic conditions with palladium catalyst. Such acid-sensitive functional groups as silyl ether and acetal moieties in the molecule were little affected by Ti-HMS, which possesses Lewis acid sites due to Ti-atom.

The selective distinction of diethylisopropylsilyl ether in hydrogenolysis

The diethylisopropylsilyl ether was distinguished from t-butyldimethysilyl, t-butyldiphenylsilyl and benzyl ethers with high selectivity in hydrogenolysis by use of Pd(OH)2 as a catalyst.

SELECTIVE DE-PROTECTION OF SILYL ETHERS

Pyridinium p-toluenesulfonate has been found to remove t-butyldimethylsilyl ethers selectively in the presence of t-butyldiphenylsilyl ethers.This methodology should find wide applicability in complex organic synthesis.

The diethylisopropylsilyl group: A new protecting group for alcohols

The diethylisopropylsilyl (DEIPS) group which is a new protective group for alcohols has been first characterized. DEIPS group can be distinguished from t-butyldimethylsilyl, triethylsilyl, tetrahydropyranyl groups and 2-deoxy glycoside with high selectivity in removing under mild acidic condition, although DEIPS group has high stability to many useful organic synthetic reaction conditions.