329313-36-2

Usage

Uses

Used in Organic Synthesis:
(S)-tert-butyldimethyl(5-phenylpent-1-yn-3-yloxy)silane is utilized as a reagent for the introduction of silyl-protected alkynyl groups into organic molecules. Its presence aids in the synthesis process, enhancing the overall efficiency and effectiveness of the reaction.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, (S)-tert-butyldimethyl(5-phenylpent-1-yn-3-yloxy)silane is used as a key intermediate for the synthesis of various pharmaceuticals. The phenyl group in its structure makes it particularly useful for creating a wide range of medicinal compounds.
Used in Agrochemical Synthesis:
Similarly, in the agrochemical industry, (S)-tert-butyldimethyl(5-phenylpent-1-yn-3-yloxy)silane serves as an essential building block for the development of various agrochemicals, contributing to the creation of effective and targeted products for agricultural use.
Used in Materials Science:
(S)-tert-butyldimethyl(5-phenylpent-1-yn-3-yloxy)silane also holds potential applications in the field of organosilicon chemistry and materials science. Its unique reactivity and structural properties make it a promising candidate for the development of new materials with specific characteristics and applications.
Overall, (S)-tert-butyldimethyl(5-phenylpent-1-yn-3-yloxy)silane is a versatile and valuable compound with diverse applications in organic synthesis, pharmaceuticals, agrochemicals, and materials research, making it an essential component in the development of innovative products and technologies across various industries.

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 183904-28-1 (S)-5-phenyl-1-pentyn-3-ol 
• 501-52-0 3-Phenylpropionic acid 
• 103-25-3 3-phenylpropanoic acid methyl ester 
• 170646-96-5 N-methoxy-N-methyl-3-phenylpropionamide 
• 895153-62-5 5-phenyl-1-(tri-isopropylsilyl)pent-1-yn-3-one 
• 895153-53-4 (S)-5-phenyl-1-(triisopropylsilyl)pent-1-yn-3-ol 
• 125303-61-9 [(2S,3S)-3-phenethyloxiran-2-yl]methanol 
• 75553-23-0 (E)-5-phenyl-2-penten-1-ol 
• 329313-35-1 C₁₁H₁₃ClO 
• 118584-91-1 5-phenylpent-1-yn-3-one 

Downstream Products

• 329313-94-2 (3R,4R)-2-methylene-3-[(3S)-3-tert-butyldimethylsiloxy-5-phenylpent-1-ynyl]-4-(tert-butyldimethylsiloxy)cyclopentan-1-one 
• 1016652-45-1 C₁₈H₂₈O₂Si 
• 1016652-28-0 (S,Z)-4-[(tert-butyldimethylsilyl)oxy]-6-phenylhex-2-yne 
• 865087-12-3 (3aR,4R,5R,6aS)-4-[3S-(t-butyldimethylsiloxy)-5-phenyl-1E-pentenyl]-5-hydroxy-hexahydro-2H-cyclopenta[b]furan-2-ol 
• 1393740-68-5 (3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol 
• 1190883-21-6 (Z)-7-((1R,2R,3R)-3-[(tert-butyldimethylsilanyl)oxy]-2-{(E)-3-[(tert-butyldimethylsilanyl)oxy]-5-phenylpent-1-en-1-yl}-5-oxo-cyclopentyl)hept-5-enoic acid isopropyl ester 
• 856240-62-5 (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2H-cyclopenta[b]furan-2,5-diol 
• 1378962-68-5 diethyl (S)-(Z)-1-tert-butyldimethylsilyloxy-6-phenyl-2-hexen-4-yl phosphate 
• 1016652-27-9 (S,Z)-6-[(tert-butyldimethylsilyl)oxy]-1-phenylhex-4-en-3-ol 
• 1016652-26-8 (S)-6-[(tert-butyldimethylsilyl)oxy]-1-phenylhex-4-yn-3-ol 
• 1016652-25-7 (S)-6-phenylhex-2-yne-1,4-diol 
• 1240483-19-5 (Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((S,E)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-enyl)-5-hydroxycyclopentyl)-N-ethylhept-5-enamide 

Relevant academic research and scientific papers

Synthesis of prostaglandin analogues, latanoprost and bimatoprost, using organocatalysis via a key bicyclic enal intermediate

Two antiglaucoma drugs, bimatoprost and latanoprost, which are analogues of the prostaglandin, PGF2?±, have been synthesized in just 7 and 8 steps, respectively. The syntheses employ an organocatalytic aldol reaction that converts succinaldehyde into a key bicyclic enal intermediate, which is primed for attachment of the required lower and upper side chains. By utilizing the crystalline lactone, the drug molecules were prepared in >99% ee.

Compound And Method

A compound of formula (I): (I) wherein Y is, Z is OR10, NR11R11 SR11, S(0)R11 S02R11, R10 is H, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, CO—R11, or a protecting group, and R11 is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, or alkoxyl; a process for making a compound of formula (I); and a process for making a prostaglandin or a prostaglandin analogue using a compound of formula (I). wherein Y is

COMPOUND AND METHOD

A compound of formula (I): (I) wherein Y is, Z is OR10, NR11R11 SR11, S(0)R11 S02R11, R10 is H, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, CO-R11, or a protecting group, and R11 is optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted heterocyclyl, or alkoxyl; a process for making a compound of formula (I); and a process for making a prostaglandin or a prostaglandin analogue using a compound of formula (I).

Regio- and stereocontrolled introduction of secondary alkyl groups to electron-deficient arenes through copper-catalyzed allylic alkylation

Copper-catalyzed allylic alkylation of azoles, a pyridine N-oxide, and fluoroarenes with secondary allylic phosphates proceeded under mild reaction conditions with excellent γ-E-selectivity. The reactions with enantioenriched allylic phosphates proceeded

New general method for regio- and stereoselective allylic substitution with aryl and alkenyl coppers derived from grignard reagents

Allylic substitution with sp2-carbon reagents (aryl and alkenyl anions) was realized by using allylic picolinates and copper reagents derived from RMgBr and CuBr-Me2S to afford anti SN2 products regioand stereoselectively. Steric and electronic factors in the reagents and the size of the methylene substituents around the allylic moiety marginally affected the selectivity. The reaction system was compatible with alkyl reagents as well. Furthermore, the substitution was applied to construction of a quaternary center and synthesis of (-)-sesquichamaenol. Electron-withdrawing nature of the pyridyl group and chelation of the C(=O)-C5H4N to MgBr2 generated in situ were found to be responsible for the high efficiency of the substitution.

Picolinoxy group, a new leaving group for anti SN2 selective allylic substitution with Aryl Anions Based on Grignard Reagents

The picolinoxy group was found to be an extremely powerful leaving group for allylic substitution with aryl nucleophiles derived from ArMgBr and CuBr?Me2S. The substitution proceeds with anti SN2 pathway and with high chirality transfer. The electron-withdrawing effect of the pyridyl group and chelation to MgBr2 are likely the origin of success. Results suggesting these effects were obtained.

Chromium(III) catalyzed synthesis of allenes from propargyl derivatives via a carbometalation-elimination sequence

The syn-carbometalation/syn-elimination of propargyl substrates to form allenes has been achieved using cationic chromium(III) catalysts activated by alkylaluminums. The mechanism and scope of this transformation are presented.

Novel 6-alkyl and 6.8-dialkylbicyclo(4.2.0)octane derivatives

Compounds useful in treating or preventing gastrointestinal ulcers and in treating cardiovascular disorders such as thrombosis, hypertension and atherosclerosis are depicted in formulas (1), (2) and (3): STR1 wherein: A is --C C--, trans --HC=CH--, trans --CH=CHCH2 -- or --CH2 CH2 --; X is lower alkyl of 1-6 carbon atoms; Y is hydrogen, exo-(lower alkyl) or endo-(lower alkyl); n is an integer from 2-4; R1 is --CH2 OH, --CHO, --CO2 R or --CO2 H, and the olefin formed by the R1 (CH2)n CH= moiety is either (E) or (Z); R2 is hydrogen or methyl, or optionally --CH=CH2 when A is trans --CH=CHCH2 --; and R3 is linear or branched alkyl, alkenyl or alkynyl having 5-10 carbon atoms, STR2 --(CH2)m -phenyl or CH2 O-phenyl; in which each phenyl may be optionally substituted with lower alkyl, lower alkoxy, trifluoromethyl, or halogen. in which: a is an integer of 0, 1 or 2; b is an integer of 3-7; m is an integer of 0, 1 or 2; and R is STR3 wherein X' is STR4 in which each R4 is independently hydrogen or lower alkyl having 1-6 carbon atoms, or a pharmaceutically acceptable, non-toxic salt or ester thereof.