120789-51-7

Usage

Uses

Used in Pharmaceutical Synthesis:
3-TERT-BUTYLDIMETHYLSILYL-2-PROPYN-1-OL is used as a key intermediate in the synthesis of pharmaceuticals for its ability to protect the alcohol group, facilitating selective reactions and enhancing the stability of the compounds during the synthesis process.
Used in Agrochemical Production:
In the agrochemical industry, 3-TERT-BUTYLDIMETHYLSILYL-2-PROPYN-1-OL is utilized as a versatile building block for the creation of various agrochemicals, contributing to the development of effective and stable products for agricultural applications.
Used in Material Science:
3-TERT-BUTYLDIMETHYLSILYL-2-PROPYN-1-OL is employed as a reagent in material science for the preparation of advanced materials, leveraging its protective and reactive properties to synthesize novel compounds with specific properties for various applications.

Upstream product

• 154673-66-2 1-(tert-butyldimethylsilyl)-3-(tert-butyldimethylsilyloxy)propyne 
• 50-00-0 formaldehyd 
• 86318-61-8 (tert-butyldimethylsilyl)acetylene 
• 74-96-4 ethyl bromide 
• 76782-82-6 tert-Butyldimethyl(prop-2-ynyloxy)silane 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 135294-85-8 tert-butyldimethyl(3-((tetrahydro-2H-pyran-2-yl)oxy)prop-1-yn-1-yl)silane 
• 107-19-7 propargyl alcohol 
• 6089-04-9 3-(tetrahydropyran-2'-yloxy)propyne 

Downstream Products

• 131365-11-2 (3-bromo-1-propynyl)tert-butyldimethylsilane 
• 176545-76-9 tertbutyldimethylsilylpropa-1,2-diene 
• 488151-78-6 1-[2-(3-tert-butyldimethylsilyl-2-propynyloxy)-3-methylphenyl]ethanone 
• 1386346-61-7 C₂₁H₂₇O₄PSi 

Relevant academic research and scientific papers

Synthesis of 3-hydroxyalkylbenzo[b]furans via the palladium-catalysed heteroannulation of silyl-protected alkynols with 2-iodophenol

The palladium-catalysed annulation of silyl-protected alkynols with 2-iodophenol gives silyl-protected 3-hydroxyalkylbenzo[b]furans 3 a-l. The use of silyl-protected propynols bearing a free hydroxyl or an O-triethylsilyl protecting group resulted in the formation of 1-oxa-2-silacyclopent-3-enes 5a-d as the major products. Removal of the silyl protecting groups from silyl benzo[b]furans 3c, 3e and 3i affords 3-hydroxyalkylbenzo[b]furans 9a-c in good yield.

Palladium-Catalysed Synthesis of Heterocondensed Pyrroles

The palladium-catalysed preparation of some heterocondensed pyrroles from ortho nitrogen containing hetaryl iodides and derivatives of propargyl alcohol is described.

Palladium(0)-catalyzed rearrangement of silicon substituted vinyloxiranes. Enantiocontrolled preparation of α-tertiodutyldimethylsilyl-β,γ-unsaturated aldehydes

Palladium(0)-catalyzed rearrangement of silicon substituted vinyloxiranes occured with a high stereoselectivity and in a very good chemical yield.

Effects of Structural Factors in Silyl Ethers Derived from Terminal Acetylenic Alcohols on 1,4-O→Csp Migration of the Silyl Group

Effects of structural factors in silyl ethers derived from terminal acetylenic alcohols on 1,4-O-→Csp migration of the silyl group in the Iotsitch reagent were studied. The effect of steric factor at the carbon atom neighboring to the reaction center was found to be stronger than that at the silicon atom in the migrating group.

Synthesis and Isolation of Organogold Complexes through a Controlled 1,2-Silyl Migration

During our efforts toward the synthesis of naturally occurring polyprenylated polycyclic acylphloroglucinol using a AuI-catalyzed 6-endo dig carbocyclization, we isolated stable vinyllic gold intermediates. Optimization lead to isolated yields of up to 98 %, using 2-(di-tert-butylphosphino)biphenyl as the ligand. This transformation is derived from a silyl rearrangement that can be fully controlled according to the nature of the substituent on the ynone. This selective transformation does not require basic conditions to prevent protodeauration. These vinylgold complexes are the first isolated intermediates during a silyl migration with gold(I). More than 16 new organogold complexes were synthesized and characterized by single-crystal X-ray diffraction. Reactivity of these complexes is also presented.

Tandem Base-Promoted Ring Opening/ Brook Rearrangement/Allylic Alkylation of O-Silyl Cyanohydrins of β-Silyl-α,β-epoxyaldehydes

(matrix presented) Metalated O-silyl cyanohydrins of β-silyl-α,β-epoxyaldehyde have been found to serve as functionalized homoenolate equivalents by a tandem sequence involving a base-promoted ring opening of the epoxide, Brook rearrangement, and alkylati

Silyl-protected propargyl glycine for multiple labeling of peptides by chemoselective silyl-deprotection

We synthesized Fmoc-propargyl glycine derivatives bearing different silyl protecting groups that can be readily introduced by using a standard solid-phase peptide coupling procedures. Taking advantage of the orthogonality between the different silyl prote

Ni-catalyzed direct carboxylation of propargylic alcohols with carbon dioxide

The carboxylation of propargylic alcohols containing a silyl group at the terminal position was conducted in a CO2 atmosphere at atmospheric pressure in the presence of a nickel catalyst and diethylzinc. Here, CO2 was used as not only the C1 source but also the promoter of the COH cleavage processes for the oxidative addition of propargylic alcohols.

Direct Access to Allenylphosphine Oxides via a Metal Free Coupling of Propargylic Substrates with P(O)H Compounds

A direct and convenient approach for the coupling of propargylic substrates with diphenylphosphine oxide in the presence of Tf2O and 2,6-lutidine has been developed. The method provides a general approach for the construction of attractive allenylphosphoryl skeletons with high atom and step economy under metal free conditions.

Probing o-diphenylphosphanyl benzoate (o-DPPB)-directed C - C bond formation: Total synthesis of dictyostatin

Herein, we report a robust total synthesis of dictyostatin. This polyketide natural product has attracted much attention because of its impressive antiproliferative activity against several human cancer-cell lines. We accomplished its synthesis in a highly convergent manner from three fragments of equal complexity, which were prepared on multigram scale. The southern and northwestern subunits were constructed through application of our o-DPPB-directed hydroformylation and allylic substitution methodology, respectively. These methods generated the C6 and C14 stereocenters of dictyostatin with good diastereoselectivities and simultaneously allowed further elaboration of the fragments by Wittig olefination and Sharpless asymmetric epoxidation, respectively. The compelling performance of the hydroformylation and allylic substitution with regard to practicability, selectivity, and scale underline their value for the construction of propionate motifs.