329313-36-2

Basic information

• Product Name: (S)-tert-butyldimethyl(5-phenylpent-1-yn-3-yloxy)silane
• Synonyms: (S)-tert-butyldimethyl(5-phenylpent-1-yn-3-yloxy)silane
• CAS NO: 329313-36-2
• Molecular Weight: 274.478
• Mol File: 329313-36-2.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (S)-tert-butyldimethyl(5-phenylpent-1-yn-3-yloxy)silane(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-tert-butyldimethyl(5-phenylpent-1-yn-3-yloxy)silane(329313-36-2)
• EPA Substance Registry System: (S)-tert-butyldimethyl(5-phenylpent-1-yn-3-yloxy)silane(329313-36-2)

Safety Data

• Hazardous Substances Data: 329313-36-2(Hazardous Substances Data)

Usage

General Description

(S)-tert-butyldimethyl(5-phenylpent-1-yn-3-yloxy)silane is a chemical compound with the chemical formula C15H24OSi. It is a silane derivative with a bulky tert-butyldimethylsilyl group and a phenylpentynyl ether substituent. (S)-tert-butyldimethyl(5-phenylpent-1-yn-3-yloxy)silane is used in organic synthesis as a reagent for the introduction of silyl-protected alkynyl groups into organic molecules. The presence of the phenyl group makes it useful in the synthesis of various pharmaceuticals, agrochemicals, and materials. It also has potential applications in the field of organosilicon chemistry and materials science due to its unique reactivity and structural properties. Overall, (S)-tert-butyldimethyl(5-phenylpent-1-yn-3-yloxy)silane is a valuable compound with diverse applications in organic synthesis and materials research.

Upstream product

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

Downstream Products

• 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 
• 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 
• 155206-00-1 bimatoprost 
• 329313-94-2 (3R,4R)-2-methylene-3-[(3S)-3-tert-butyldimethylsiloxy-5-phenylpent-1-ynyl]-4-(tert-butyldimethylsiloxy)cyclopentan-1-one 
• 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 

Relevant articles and documents

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).

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.