147649-96-5

Upstream product

• 79563-29-4 (S)-4-isopropyl-3-((R)-2-methylpent-4-enoyl)oxazolidin-2-one 
• 100-51-6 benzyl alcohol 
• 96930-18-6 (4R,5S)-4-methyl-3-pent-4-enoyl-5-phenyloxazolidin-2-one 
• 149065-49-6 2-methylpent-4-enoic acid chloride 
• 3017-53-6 benzyl 2-bromopropionate 
• 90891-07-9 benzyl 2-iodopropanoate 
• 81577-34-6 benzyl 2-chloropropanoate 
• 927-77-5 n-propylmagnesium bromide 
• 157056-90-1 diallylmethoxyborane 
• 2622-05-1 allylmagnesium bromide 
• 1575-74-2 (+-)-2-methyl-pent-4-enoic acid 
• 153946-47-5 (4R,5S,2'S)-4-cyclohexyl-1,5-dimethyl-3-(2-methylpent-4-enoyl)imidazolidin-2-one 

Downstream Products

• 116492-52-5 benzyl (R)-2-methyl-4-oxabutanoate 
• 410081-27-5 (2R,3R,4R)-4-(N-(tert-butyloxy)carbonyl-N-methyl)amino-2,3-di(4-methoxybenzyl)oxy-5-methoxy-N-(3R-((4-methoxycarbonyl)-2-oxazolyl)-1-butyl)pentamide 
• 144681-93-6 2-{(R)-3-[(2R,3R,4R)-2,3-Bis-benzyloxy-4-(tert-butoxycarbonyl-methyl-amino)-5-methoxy-pentanoylamino]-1-methyl-propyl}-oxazole-4-carboxylic acid methyl ester 
• 1276653-17-8 bis{4-(allyloxy)-3,5-dimethoxyphenyl}methanone 
• 1355235-10-7 (R)-1,1-bis(4-(allyloxy)-3,5-dimethoxyphenyl)-2-methylpent-4-en-1-ol 
• 1355235-08-3 (R)-5,5-bis(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)-4-methyldihydrofuran-2(3H)-one 
• 1355235-05-0 (3R,4R)-5,5-bis(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-one 
• 1355235-12-9 ((((3R,4R)-3,4-dimethyltetrahydrofuran-2,2-diyl)bis(2,6-dimethoxy-4,1-phenylene))bis(oxy))bis(tert-butyldimethylsilane) 
• 848986-18-5 (-)-sacidumlignan D 
• 1355235-06-1 (2R,3S)-4,4-bis(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)-2,3-dimethylbutan-1-ol 
• 1355235-09-4 (R)-1,1-bis(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)-2-methylpent-4-en-1-ol 
• 1355235-13-0 C₂₂H₂₈O₇ 
• 143225-28-9 benzyl (R)-2-methyl-4-pentenoate 
• 147649-97-6 benzyl 2-methyl-4-oxabutanoate 

Relevant academic research and scientific papers

C-C Bond Cleavage of Unactivated 2-Acylimidazoles

2-Acylimidazoles are widely used as post-Transformable carboxylic acid equivalents in chemoselective and enantioselective reactions. Their transformations, however, require pretreatment with highly reactive, toxic methylating reagents to facilitate C-C bond cleavage. Here, we demonstrate that such pretreatment can be avoided and the C-C bond cleaved under neutral conditions without the use of additional reagents or catalysts. The scope of the reaction, including the use of products reported in the literature as substrates, and some mechanistic insights are described.

Cyclic comonomers for the synthesis of carboxylic acid and amine functionalized poly(L-lactic acid)

Degradable aliphatic polyesters such as poly(lactic acid) are widely used in biomedical applications, however, they lack functional moieties along the polymer backbone that are amenable for functionalization reactions or could be the basis for interactions with biological systems. Here we present a straightforward route for the synthesis of functional α-ω epoxyesters as comonomers for lactide polymerization. Salient features of these highly functionalized epoxides are versatility in functionality and a short synthetic route of less than four steps. The α-ω epoxyesters presented serve as a means to introduce carboxylic acid and amine functional groups into poly(lactic acid) polymers via ring-opening copolymerization.

Sensing remote chirality: Stereochemical determination of β-, γ-, and δ-chiral carboxylic acids

Determining the absolute stereochemisty of small molecules bearing remote nonfunctionalizable stereocenters is a challenging task. Presented is a solution in which appropriately substituted bis(porphyrin) tweezers are used. Complexation of a suitably derivatized β-, γ-, or δ-chiral carboxylic acid to the tweezer induces a predictable helicity of the bis(porphyrin), which is detected as a bisignate Cotton Effect (ECCD). The sign of the ECCD curve is correlated with the absolute stereochemistry of the substrate based on the derived working mnemonics in a predictable manner.

Radical allylation, vinylation, alkynylation, and phenylation reactions of α-halo carbonyl compounds with organoboron, organogallium, and organoindium reagents

Allylic gallium and indium reagents are found to mediate radical allylation reactions of α-iodo or α-bromo carbonyl compounds. Treatment of benzyl bromoacetate with allylgallium, prepared from allylmagnesium chloride and gallium trichloride, in the presence of triethylborane provided benzyl 4-pentenoate in excellent yield. Addition of water as a co-solvent improved the yields of allylated products. Allylic indium reagents are also useful and can replace the gallium reagents. A diallylborane reagent can allylate an α-iodo ester in good yield. Alkenylation reactions of α-halo carbonyl compounds with alkenylindium proceeded via a radical process in the presence of triethylborane. Unactivated alkene moieties and styryl groups were introduced by this method. The carbon-carbon double bond geometry of the alkenylindiums was retained during the alkenylation. Preparation of an alkenylindium via a hydroindation of 1-alkyne and subsequent radical alkenylation established an efficient one-pot strategy. Radical alkynylations and phenylations with organoindium reagents are disclosed herein.

Triethylborane-Induced Radical Allylation Reaction with Zirconocene-Olefin Complex

(Matrix presented) Allylzirconium reagents are effective for radical allylation of α-halo carbonyl compounds. The key steps would be homolytic cleavage of the zirconium-carbon bond and halogen abstraction by the resulting Cp2ZrCI(III). Zirconoc

Applications of crotyldiisopinocampheylboranes in synthesis: A formal total synthesis of (+)-calyculin A

The formal total synthesis of the marine metabolite (+)-calyculin A is reported. The key steps involve (i) the use of Brown allylboration chemistry to control the relative and absolute stereochemistry of homoallylic alcohol arrays, thus setting eight of the desired stereocenters; (ii) Stille coupling methodology in the construction of the cyano tetraene unit of the natural product; and (iii) a modified Cornforth-Meyers approach to the synthesis of the oxazole fragment.

Triethylborane-induced radical allylation of α-halo carbonyl compounds with allylgallium reagent in aqueous media

An allylgallium reagent is found to be effective for radical allylation of α-iodo or α-bromo carbonyl compounds. Treatment of benzyl bromoacetate with allylgallium, prepared from allylmagnesium chloride and gallium trichloride, in the presence of triethylborane in THF provided benzyl 4-pentenoate in good yield. The addition of water as a cosolvent improved the yields of allylated products. It was revealed that the allylgallium species resists immediate decomposition on exposure to water.

SUBSTITUTED OXOTREMORINE DERIVATIVES

This disclosure describes novel substituted oxotremorine derivatives of formula I having nitrogen, oxygen or sulfur groups and the prodrug forms of these derivatives. The compounds have cholinergic activity. Also disclosed are methods for treating diseases of the central nervous system in mammals employing the compounds, pharmaceutical preparations containing the compounds and the processes for the production of the compounds. STR1

Substituted oxotremorine derivatives and pharmaceutical use thereof

This disclosure describes novel substituted oxotremorine derivatives of formula I having nitrogen, oxygen or sulfur groups and the prodrug forms of these derivatives. The compounds have cholinergic activity. Also disclosed are methods for treating disease

The synthesis and biochemical pharmacology of enantiomerically pure methylated oxotremorine derivatives

Previous pharmacological studies of methylated oxotremorine derivatives bearing substituents at the 3-, 4-, and 5-positions of the pyrrolidinone ring have been conducted using racemic mixtures, and not with optically active compounds. The synthesis and radioligand binding data of optically active, methylated oxotremorine derivatives at the 3- and 4-positions are described. There are significant pharmacological differences between the 3- and 4- position derivatives. The 4-position enantiomers have weak, approximately equal affinity and antagonist-like profiles, whereas the 3-position enantiomers have significantly different affinities and partial agonist-like profiles.