1775-44-6

Upstream product

• 20515-15-5 methyl (2E)-4-methylpent-2-enoate 
• 141-82-2 malonic acid 
• 78-84-2 isobutyraldehyde 
• 69143-05-1 (E)-4-methyl-pent-2-en-1-ol 
• 3095-95-2 diethylphosphonoacetic acid 
• 40309-42-0 ethyl 3-hydroxy-4-methylpentanoate 
• 65946-59-0 (trimethylsilyl)ketene bis(trimethylsilyl) acetal 
• 15790-86-0 ethyl-4-methyl-2-(E)-penteneoate 
• 1669-43-8 (E)-4-isopropylbut-3-en-2-one 

Downstream Products

• 93759-96-7 N-Benzyl-DL-erythro-β-hydroxy-leucin 
• 85390-10-9 (E)-4-Methyl-pent-2-enoic acid {2-[4-(3-cyclohexyl-2-imino-imidazolidine-1-sulfonyl)-phenyl]-ethyl}-amide 
• 194031-58-8 (4R,2E)-3-(1-oxo-2-isohexenyl)-4-phenyl-2-oxazolidinone 
• 201142-33-8 (2S,3S)-1-((1R,5R,6R)-6-Hydroxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl)-3-methyl-pent-4-yne-2,3-diol 
• 175853-66-4 (2S,3R)-2-azido-3-phenylisohexanoic acid 
• 199468-82-1 (2R,3R)-2-azido-3-phenylisohexanoic acid 
• 199468-81-0 (2S,3S)-2-azido-3-phenylisohexanoic acid 
• 199468-83-2 (2R,3S)-2-azido-3-phenylisohexanoic acid 
• 176018-91-0 (S)-3-((S)-4-Methyl-3-phenyl-pentanoyl)-4-phenyl-oxazolidin-2-one 
• 176018-92-1 (R)-3-((R)-4-Methyl-3-phenyl-pentanoyl)-4-phenyl-oxazolidin-2-one 
• 199468-77-4 (S)-3-((2S,3S)-2-Bromo-4-methyl-3-phenyl-pentanoyl)-4-phenyl-oxazolidin-2-one 
• 175853-64-2 (R)-3-((2R,3R)-2-Bromo-4-methyl-3-phenyl-pentanoyl)-4-phenyl-oxazolidin-2-one 
• 175853-65-3 (R)-3-((2S,3R)-2-Azido-4-methyl-3-phenyl-pentanoyl)-4-phenyl-oxazolidin-2-one 
• 199468-80-9 (S)-3-((2R,3S)-2-Azido-4-methyl-3-phenyl-pentanoyl)-4-phenyl-oxazolidin-2-one 

Relevant academic research and scientific papers

COVALENT RAS INHIBITORS AND USES THEREOF

The disclosure features compounds, or pharmaceutically acceptable salts thereof, alone and in combination with other therapeutic agents, pharmaceutical compositions, and protein conjugates thereof, capable of modulating biological processes including Ras, and their uses in the treatment of cancers.

RAS INHIBITORS

The disclosure features macrocyclic compounds, and pharmaceutical compositions and protein complexes thereof, capable of inhibiting Ras proteins, and their uses in the treatment of cancers.

Chiral integrated catalysts composed of bifunctional thiourea and arylboronic acid: Asymmetric aza-Michael addition of α,β-unsaturated carboxylic acids

The first intermolecular asymmetric Michael addition of nitrogen-nucleophiles to α,β-unsaturated carboxylic acids was achieved through a new type of arylboronic acid equipped with chiral aminothiourea. The use of BnONH2 as a nucleophile gives a range of enantioenriched β-(benzyloxy)amino acid derivatives in good yields and with high enantioselectivity (up to 90% yield, 97% enantiomeric excess (ee)). The obtained products are efficiently converted to optically active β-amino acid and 1,2-diamine derivatives.

Application of chiral ligands: Carbohydrates, nucleoside-lanthanides and other Lewis acid complexes to control regio- and stereoselectivity of the dipolar cycloaddition reactions of nitrile oxides and esters

Chiral Lewis acid mediated 1,3-dipolar cycloaddition reactions of 4-trifluoromethylbenzonitrile oxide to methyl crotonate as well to β-substituted acrylates and (Z)-pent-2-en-1-yl esters were examined. Excellent enantioselectivities with moderate to good regioselectivities were achieved for crotonates with complexes of BiBr3 with (+)-(4,6-benzylidene)methyl-α-d-glucopyranoside C, with the l-ascorbic acid I-FeCl3 system, and with lipase Candida antarctica. High enantiomeric excess was observed for isopropyl ester and benzyl ester. The outstanding ee values were achieved for acrylates with β-t-butyl, cyclohexyl, and 1,3-benzodioxol-5-yl groups in cycloadditions catalyzed by C-Yb(OTf)3 and the (+)-2-hydroxy-3-pinanone N-TiCl4 system. High enantioselectivities were found in reactions of (Z)-pent-2-en-1-yl esters mediated by complexes N-Mg(OTf)2 and N-TiCl4.

Synthetic approaches to the daucane sesquiterpene derivatives employing the intramolecular Buchner cyclisation of α-diazoketones

The use of the intramolecular Buchner cyclisation of an α-diazoketone as an approach to the synthesis of daucane sesquiterpenes is described; in particular the synthesis of the cis-fused analogue of dihydro CAF-603. The key step in the synthesis is the intramolecular Buchner cyclisation, which provides the bicyclo[5.3.0]decane framework with the required stereochemistry at the quaternary centre generated in the cyclisation. A synthetic route enabling access to an asymmetric synthesis is also outlined.

Asymmetric synthesis of cis-7-methoxycalamenene via the intramolecular buchner reaction of an α-diazoketone

The asymmetric synthesis of cis-7-methoxycalamenene 1 has been accomplished using the intramolecular Buchner reaction of α-diazoketone 7 as the key step in the synthetic route. Upon reduction of the equilibrating azulenone structure 8, the resulting azulenol 9 rearranges to dihydronaphthalene 10 containing the 6,6-membered bicyclic ring system characteristic of 1, by means of an acid-catalyzed aromatization process. Transformation of 10 to 1 is accomplished through a three-step reaction sequence.

β-alanine-DBU: A highly efficient catalytic system for knoevenagel-doebner reaction under mild conditions

A mild and efficient Knoevenagel-Doebner reaction from malonic acid and a wide range of aldehydes was catalyzed by a catalytic system consisting of β-alanine and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), affording the corresponding (E)-α,β-unsaturated carboxylic acids in good to excellent yields and with high stereoselectivity. The advantage of the method is that the reaction could proceed smoothly at ambient temperature so that it can tolerate a variety of functional groups and avoid unnecessary side reactions. Copyright

METHOD FOR THE DECARBOXYLATIVE HYDROFORMYLATION OF ALPHA, BETA- UNSATURATED CARBOXYLIC ACIDS

The present invention relates to a process for preparing aldehydes by reacting an α,β-unsaturated carboxylic acid or a salt thereof with carbon monoxide and hydrogen in the presence of a catalyst comprising at least one complex of a metal of transition group VIII of the Periodic Table of the Elements with at least one compound of the formula (I), where Pn is pnicogen; W is a divalent bridging group having from 1 to 8 bridge atoms between the flanking bonds; R1 is a functional group capable of forming at least one intermolecular, noncovalent bond with the —X(═O)OH group of the compound of the formula (I); R2, R3 are each in each case optionally substituted alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl or together with the pnicogen atom and together with the groups Y2 and Y3 if present form an optionally fused and optionally substituted 5- to 8-membered heterocycle; a, b and c are each 0 or 1; and Y1,2,3 are each, independently of one another, O, S, NRa or SiRbRc, where Ra,b,c are each H or in each case optionally substituted alkyl, cycloalkyl, heterocycloalkyl, aryl or hetaryl; and the use of the above-described catalyst for the decarboxylative hydroformylation of α,β-unsaturated carboxylic acids.

Combined transition-metal- and organocatalysis: An atom economic C3 homologation of alkenes to carbonyl and carboxylic compounds

A combination of regioselective room-temperature/ambient-pressure hydroformylation (transitionmetal catalysis) and decarboxylative Knoevenagel reactions (organocatalysis) allowed for the development of an efficient, one-pot C3 homologation of terminal alkenes to (E)-α,β-unsaturated acids and esters, (E)-β,γ-unsaturated acids, (E)-α-cyano acrylic acids, and α,β-unsaturated nitriles. All reactions proceed under mild conditions, tolerate a variety of functional groups, and furnish unsaturated carbonyl compounds in good yields and with excellent regioand stereocontrol. Further, an iterative C2 homologation of (E)-α,β-unsaturated carboxylic acids is possible through a combination of decarboxylative hydroformylation employing a supramolecular catalyst followed by decarboxylative Knoevenagel condensation with an organocatalyst.

A supramolecular catalyst for the decarboxylative hydroformylation of α,β-unsaturated carboxylic acids

(Chemical Equation Presented) Head 'em up, move 'em out, aldehyde! A catalytic transformation of α,β-unsaturated carboxylic acids into aldehydes through a hydroformylation-decarboxylation process has been developed (see scheme; Do = donor ligand, FG1 and FG2 = complementary functional groups). The reaction proceeds at mild conditions, tolerates many functional groups, and liberates CO2 as the only stoichiometric by-product.