109958-86-3

Usage

InChI:InChI=1/C5H9NO2/c1-3-5(2,6)4(7)8/h3H,1,6H2,2H3,(H,7,8)/t5-/m1/s1

Upstream product

• 16820-10-3 5-methyl-5-vinyl-imidazolidine-2,4-dione 
• 80-59-1 Tiglic acid 
• 74761-84-5 (+/-)-N-benzoyl-α-vunylalanine methyl ester 
• 74761-87-8 2-Benzoylamino-2-methyl-but-3-enoic acid 
• 353456-95-8 2-methyl-2-(toluene-4-sulfonylamino)-but-3-enoic acid 
• 882048-79-5 N-(9-fluorenylmethoxycarbonyl)-α-vinylalanine 
• 882048-62-6 N-(p-methoxyphenyl)-O-(tetrahydro-2'H-pyran-2'-yl)-α-vinylalaninol 
• 882048-75-1 N-(9-fluorenylmethoxycarbonyl)-α-vinylalaninol 
• 882048-51-3 N-(p-methoxyphenyl)-O-(tetrahydro-2'H-pyran-2'-yl)-N-trifluoroacetyl-α-vinylalaninol 
• 98262-63-6 (2R,5R)-1-benzoyl-2-(tert-butyl)-3,5-dimethyl-5-(3'-thiabutyl)imidazolidin-4-one 
• 160708-74-7 N-((R)-1-Hydroxymethyl-1-methyl-allyl)-benzamide 
• 162717-62-6 N-((R)-1-Formyl-1-methyl-allyl)-benzamide 
• 140867-28-3 (+/-)-N-benzoyl-α-vinylalaninol 
• 314774-35-1 (4R,5S)-4-Methyl-2-phenyl-5-phenylselanylmethyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Polyenolates of unsaturated carboxylic acids in synthesis. Synthesis of unsaturated α-amino acids and γ-hydrazino acids

Regioselective reaction of lithium diene- and triene-diolates 1 and 2 with o-diphenylphosphinyl hydroxylamine affords unsaturated α-amino acids 3 and 4. Addition to DEAD leads selectively to γ-hydrazino unsaturated acids 5 and 6.

One-Pot Vinylation of Azlactones: Fast Access to Enantioenriched α-Vinyl Quaternary Amino Acids

We report a fast one-pot protocol for the direct vinylation of azlactones [oxazol-5-(4H)-ones] by using as a key step an aldol addition with 2-(phenylselenenyl)acetaldehyde followed by dehydroxyselenation. The acid hydrolysis of the oxazolone ring gave the desired fully deprotected α-vinyl quaternary α-amino acids in almost quantitative yields. An enantioselective variant of the method was also developed by using catalytic chiral bases. The use of Sharpless ligand (DHQD)2PHAL produced the final quaternary amino acids in good overall yields (62–78 %) and with ee values up to 86 %. Scaling up the optimized protocol to gram quantities did not affect the yields and ee values. We also demonstrated that the vinyl moiety installed onto the oxazolone ring can be exploited as a handle for the attachment of aryl groups through a Heck coupling reaction.

A formal [3,3]-sigmatropic rearrangement route to quaternary α-vinyl amino acids: Use of allylic N-PMP trifluoroacetimidates

Pd(II)-mediated rearrangement of allylic N-PMP (p-methoxyphenyl) trifluoroacetimidates provides the first formal sigmatropic route to quaternary, α-vinylic amino acids, potential suicide substrates for PLP enzymes. The amino acid side chains enter via tra

AMINO ALCOHOL DERIVATIVES

The present invention relates to compounds of formula (I) which exhibit excellent immune suppression activity, pharmacologically acceptable salts thereof, esters thereof or other derivatives: wherein R1 and R2 are a hydrogen atom, an amino protecting group; R3 is a hydrogen atom, a hydroxy protecting group; R4 is a lower alkyl group; n is an integer from 1 to 6; X is an ethylene group; Y is a C1-C10 alkylene group, a C1-C10 alkylene group substituted with 1 to 3 substituents selected from substituent group a and b; R5 is an aryl group; R6 and R7 are a hydrogen atom, a group selected from substituent group a; with the proviso when R5 is a hydrogen atom, Y is not a single bond or a straight chain C1-C10 alkylene group.

Amino alcohol derivatives

Compounds of formula (I) which exhibit excellent immune suppression activity, pharmacologically acceptable salts thereof, esters thereof or other derivatives: wherein R1 and R2 are a hydrogen atom, an amino protecting group; R3 is a hydrogen atom, a hydroxy protecting group; R4 is a lower alkyl group; n is an integer from 1 to 6; X is an ethylene group; Y is a C1-C10 alkylene group, a C1-C10 alkylene group substituted with 1 to 3 substituents selected from substituent group a and b; R5 is an aryl group; R6 and R7 are a hydrogen atom, a group selected from substituent group a; with the proviso when R5 is a hydrogen atom, Y is not a single bond or a straight chain C1-C10 alkylene group.

Aziridination of 5-methyl-4H-1,3-dioxins by N-tosyliminophenyliodinane: A one-step procedure for the synthesis of α-methylserinal derivatives

The methyl analogue of Garner's aldehyde, N-tosyl-4-methyl-N, O-isobutyrylideneserinal, has been prepared in a one-step reaction by CuClO4-catalyzed aziridination of 2-isopropyl-5-methyl-4 H-1,3-dioxin with N-tosyliminophenyliodinane and transformed into α-methylserine derivatives, e.g. α-vinylalanine.

Enantiomerically enriched α-vinyl amino acids via lipase-mediated "reverse transesterification"

Reduction of protected α-vinyl amino acids produces "neopentyl" alcohols that may be enriched in the L-antipode by lipase-mediated acylation with vinyl acetate. Subsequent deacetylation, oxidation and hydrolysis yields enantiomerically enriched L-α-vinyl

Formal α-Vinylation of Amino Acids. Use of a New Benzeneselenolate Equivalent

A new synthetic approach to the formal α-vinylation of α-amino acids is described, in which the readily available electrophile, ethylene oxide, serves as the vinyl cation equivalent.N-Benzoyl α-amino esters bearing appropriate side-chain protecting groups

Asymmetric Synthesis of α-Alkyl-α-amino Acids from Chromium-Carbene-Complex-Derived β-Lactams

Optically active bicyclic β-lactam 3 was synthesized by photolysis of optically active oxazolidine carbene chromium complex 1 with oxazine 2.Conversion of the oxazolidine to the oxazolidinone gave a bicyclic β-lactam readily α-alkylated.Cleavage of the alkylated β-lactam gave optically active ester aldehyde 7, which was converted to a number of optically active α-alkyl-α-amino acids.These include (R)-α-methylserine, (S)-α-methylglutamic acid, (S)-α-methylornithine, (S)-vinylalanine, (S)-ethynylalanine, and (S)-2-methyl-2,3-diaminopropionic acid.