17993-97-4

Upstream product

• 100-52-7 benzaldehyde 
• 18243-38-4 (trimethylsilyl)methylmagnesium bromide 
• 13170-43-9 (trimethylsilyl)methylmagnesium chloride 
• 75-89-8 2,2,2-trifluoroethanol 
• 2344-80-1 Chloromethyltrimethylsilane 
• 41924-27-0 tris[(trimethylsilyl)methyl]aluminum 
• 93-97-0 benzoic acid anhydride 
• 66222-28-4 (benzyloxymethyl)tributylstannane 
• 84507-45-9 1-phenyl-2-(trimethylsilyl)ethyl acetate 
• 97364-08-4 (trimethylsilyl)methyltriisopropoxytitanium 
• 110935-07-4 Butyltellanylmethyl-trimethyl-silane 
• 75-77-4 chloro-trimethyl-silane 
• 156454-67-0 benzyl (trimethylsilyl)methyl ether 
• 13735-78-9 1-phenyl-2-(trimethylsilyl)ethanone 

Downstream Products

• 100-42-5 styrene 
• 1066-40-6 Trimethylsilanol 
• 84507-45-9 1-phenyl-2-(trimethylsilyl)ethyl acetate 
• 136272-18-9 Trifluoro-acetic acid 1-phenyl-2-trimethylsilanyl-ethyl ester 
• 1187667-24-8 (2-(4-methoxybenzyloxy)-2-phenylethyl)trimethylsilane 
• 58541-16-5 N-(α-Phenyl-β-trimethylsilylaethyl)-anilin 
• 19372-00-0 1-(trimethylsilyl)-2-phenylethene 
• 6337-27-5 4-Phenylcyclohex-4-ene-1,2-carboxylic anhydride 
• 111077-32-8 2-Phenyl-1-(trimethylsilyl)but-3-en-2-ol 
• 2288-18-8 2-phenyl-1,3-butadiene 
• 58541-13-2 Phenyl-carbamic acid 1-phenyl-2-trimethylsilanyl-ethyl ester 

Relevant academic research and scientific papers

Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols

The arylboronic acid catalyzed dehydrative C-alkylation of 1,3-diketones and 1,3-ketoesters using secondary benzylic alcohols as the electrophile is reported, forming new C-C bonds (19 examples, up to 98% yield) with the release of water as the only byproduct. The process is also applicable to the allylation of benzylic alcohols using allyltrimethylsilane as the nucleophile (12 examples, up to 96% yield).

The β-Silyl Effect on the Memory of Chirality in Friedel-Crafts Alkylation Using Chiral α-Aryl Alcohols

Iron salt-catalyzed Friedel-Crafts alkylation of chiral α-aryl alcohols with a trimethylsilyl group was found to proceed with retention of the configuration of the hydroxyl group as a leaving group. The memory of chirality of this system stems from the β-

Pharmaceutical compositions as inhibitors of dipeptidyl peptidase-IV (DPP-IV)

The present invention relates to compounds, which inhibit dipeptidyl peptidase IV (DPP-IV) and are useful for the prevention or treatment of diabetes, especially type II, as well as hyperglycemia, metabolic syndrome, hyperinsulinemia, obesity, atheroscler

Discovery of ((4R,5S)-5-amino-4-(2,4,5-trifluorophenyl)cyclohex-1-enyl)-3- (trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-7(8H-yl)methanone (ABT-341), a highly potent, selective, orally efficacious, and safe dipeptidyl peptidase IV inhibitor

Dipeptidyl peptidase IV (DPP4) deactivates glucose-regulating hormones such as GLP-1 and GIP, thus, DPP4 inhibition has become a useful therapy for type 2 diabetes. Optimization of the high-throughput screening lead 6 led to the discovery of 25 (ABT-341),

Tris(trimethylsilylmethyl)alane: An aldehyde selective peterson methylenation reagent

Tris(trimethylsilylmethyl)alane (TTMA) is a rapid, efficient, and highly aldehyde-selective trimethylsilylmethylating reagent. A solid lithium halide complex of the reagent, TTMA·3LiBr (TTMAs), is particularly effective in this transformation to the Peterson alcohol intermediate.

Stereoselective Synthesis of (1R,2S)-2-Amino-1,3-diols from (R)-Cyanohydrins

Vinyl substituted (1R,2S)-amino alcohols 5 were obtained by addition of vinyl magnesium bromide to the corresponding cyanohydrin O-trimethylsilyl ethers (R)-2.The O- and N-protected vinyl amino alcohols 6 were ozonized at -78 deg C in methanol yielding (1R,2S)-2-amino-1,3-diols 7 in high enantiomeric and diastereomeric excesses.For purification, compounds 7 in some cases were acetylated to give the derivatives (1R,2S)-8.Racemic 6a was converted by oxidative ozonolysis at -78 deg C in methanolic NaOH solution to the corresponding methyl N-acetyl-β-hydroxy propanoate 9a.The configuration of (1R,2S)-8a was confirmed by x-ray crystallographic analysis.

Silicon Effects. V. β-Silicon Effect in the Solvolysis of 2-Phenylethyl Compounds

The rates of the solvolysis of 2-aryl-2-(trimethylsilyl)ethyl compounds, ArCH(SiMe3)CH2X (4: X=Cl and OCOCF3; Ar=C6H5 and p-MeOC6H4), have been measured in various solvents at 25 deg C.The solvolysis of the chloride, 4 (X=Cl; Ar=C6H5), exhibited an m valu

Heteroatom-facilitated lithiations of N-methyl-N-(trimethylsilyl)methyl-benzylamine and benzyl (trimethylsilyl)methyl ether with butyllithium

Lithiation of the Si-methyl groups of N-methyl-N-[(trimethylsilyl)methyl]benzylamine (1) occurred in preference to ortho-lithiation of the benzyl group with butyllithium in ether. In a similar reaction with benzyl (trimethylsilyl)methyl ether (7), lithiat

Mechanism of Thermal Eliminations. Part 30. Pyrolysis of 2-Trimethylsilylethanol and 1-Aryl Derivatives

The Arrhenius parameters (Eact = 45.57 kcal mol-1, log A/s-1 = 12.865) and rate coefficient at 600 K (1.84 * 10-4 s-1) for the cis β-thermal elimination of trimethylsilanol from 2-trimethylsilylethanol are identical (within experimental error) with those reported in the literature for elimination of methyl trimethylsilyl ether from 1-methoxy-2-(trimethylsilyl)ethane.This indicates that the driving force for the reaction, formation of the Si-O bond, is such that alteration of the nucleophilicity of oxygen has little effect on the reaction rate.A series of 1-aryl-2-trimethylsilylethanols have been prepared and their rates of elimination determined.The activating effect of the 1-aryl substituent (5.2-fold) is much less than the corresponding effect in the pyrolysis of ethyl acetates (63-fold) and 2-trimethylsilylethyl acetates (87-fold).Breaking of the α-C-O bond is thus kinetically less important than in the other reactions, and this conclusion is confirmed by a correlation of the rate data with the Yukawa-Tsuno equation which gives ρ = -0.4, r = 0.3.Si-O bond formation in the reaction is thereby shown to be of over-riding kinetic importance.For the 4-methylphenyl- and 4-methoxyphenyl compounds a minor competing reaction was the elimination of water to give the corresponding 1-aryl-2-trimethylsilylethene, and this has a higher activation energy than for the elimination of trimethylsilanol.NMR spectra for the 1-aryl-2-trimethylsilylethanols show that interaction between the OH and SiMe3 groups inhibits free rotation about the C(1)-C(2) bond.Preparation of 1-aryl-2-trimethylsilylethanols gave 1,3-diaryl-4-trimethylsilylbutyl trimethylsilyl ethers as byproducts arising from elimination of water from two molecules of the alcohols in a process believed to be two-step.

Silicon Effects. II. Structure and Stability of 1-Phenyl-2-(trimethylsilyl)ethyl Cation in Solution

Solvolysis rates have been measured in various solvents at 25 deg C for 1-(substituted phenyl)-2-(trimethylsilyl)ethyl trifluoroacetates (1a - 1g; R=H, 4-Me, 4-Cl, 4-Br, 3-Cl, 3,4-Cl2, and 3,5-Cl2, respectively) and structurally related compounds, 1-phenylethyl-, 3,3-dimethyl-1-phenylbutyl-, and 1-(4-methylphenyl)ethyl trifluoroacetates (3a, 4, and 5).In dioxane/water mixtures 1g solvolyzes with the same sensitivity to the change in solvent ionizing power as that for a kc substrate 5.The solvolyses of 1e and 5 exhibit almost identical α-deuterium kinetic isotope effects (kH/KD) of 1.18 - 1.19 in aq dioxane.Substituent effect on the solvolysis of 1 in 90 percent aq dioxane is expressed by an LArSR equation: log kX/kH = -3.05 (?0 + 1.05 Δ?(mean)+R) (R = 0.9997).These findings are consistent with kc mechanism for the solvolysis of 1.Relative rates for the solvolysis of 1a, 3a, and 4 in 30 percent aq dioxane are 2.99x105:2.84:1.0 indicating solvolytic generation of α-(trimethylsilylmethyl)benzyl cation to be about 7 kcal mol-1 energetically more favorable than that of the corresponding α-alkylbenzyl cations.