90493-96-2

Usage

General Description

The chemical 1,3-dioxolane-4-carbonyl chloride, 2,2-dimethyl-, also known as dimethyl oxalyl chloride, is a colorless liquid that is commonly used in organic synthesis as a reagent for the introduction of the oxalyl group. It is a potent acylating agent and is used in the synthesis of various pharmaceuticals, agrochemicals, and dyes. It reacts violently with water and alcohols, and should be handled with extreme care due to its strong acidic and corrosive nature. This chemical is primarily used in the preparation of active pharmaceutical ingredients and is an important building block in organic chemistry.

Upstream product

• 14028-61-6 potassium (R)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 
• 114746-70-2 (R)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid 
• 5736-03-8 (d,l) isopropylidene glyceraldehyde 
• 83400-91-3 2,2-dimethyl-1,3-dioxolane-4-carboxylic acid potassium salt 
• 14028-61-6 Kaliumsalz der O-Isopropyliden-D-glycerinsaeure 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 5736-06-1 2,3-dihydroxypropionic acid isopropylidene ketal 
• 135547-99-8 2,2-dimethyl-1,3-dioxolane-4-carboxylic acid calcium salt 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 22323-82-6 (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol 

Downstream Products

• 533-50-6 D-erythrulose 
• 148065-34-3 (R)-2,2-dimethyl-1,3-dioxolane-4-carboxamide 
• 104017-05-2 phenyl 1,2-O-isopropylidene-D-glycerate 
• 949087-01-8 (+)-N,N'-{2-[(benzyloxy)imino]propane-1,3-diyl}bis{[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]carboxamide} 
• 16354-97-5 [(R)-2,2-dimethyl-1,3-dioxolan-4-yl]phenylmethanone 
• 170164-82-6 (R)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)-3-phenylpropan-1-one 
• 201420-74-8 [(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol 
• 73945-72-9 Benzoic acid 2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-oxo-ethyl ester 
• 148065-34-3 (+/-)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid amide 
• 149775-92-8 benzyl (2S,5R)-2-<(tert-butoxycarbonyl)amino>-5,6-isopropylidenedioxy-4-oxohexanoate 
• 149775-93-9 benzyl (2R,5R)-2-<(tert-butoxycarbonyl)amino>-5,6-isopropylidenedioxy-4-oxohexanoate 
• 855526-46-4 2,2-dimethyl-N-ethyl-N-phenyl-1,3-dioxolane-4-carboxamide 
• 74006-37-4 2-(2',2'-Dimethyl-1',3'-dioxolan-4'-yl)-2-oxoethylbenzoate 
• 347848-71-9 1-((R)-2,2-Dimethyl-1,3-dioxolan-4-yl)-1-[(3S,4S)-3-((R)-1-hydroxyethyl)-4-(3-hydroxy-4-methoxyphenyl)-3-methylpyrrolidin-1-yl)methanone 

Relevant academic research and scientific papers

Preparation method of sofosbuvir key intermediate

The invention discloses a preparation method of a sofosbuvir key intermediate ((2R,3R,4R,5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)benzoic acid methyl ester. The preparation method comprises the following steps: by using (R)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid as a starting material, performing acylating chlorination, performing a reaction with alpha-fluoropropionic acid, performing carbonyl reduction, performing hydroxyl protection, performing hydrolytic cyclization, performing hydroxymethyl protection, performing reduction, and performing chlorination to prepare the sofosbuvir key intermediate ((2R,3R,4R,5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)benzoic acid methyl ester. The preparation scheme has a short synthetic route and a high yield, and avoids a fluorination reaction step in the synthetic process.

SPIROCYCLIC HAT INHIBITORS AND METHODS FOR THEIR USE

Compounds having a structure of Formula (IX) or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof, wherein R1, R2a, R2b, R3a, R3b, R4a, R4b, Q1----Q2, R6, R7, A, B, W, x, and y are as defined herein and are provided. Pharmaceutical compositions comprising such compounds and methods for treating various HAT-related conditions or diseases, including cancer, by administration of such compounds are also provided.

Synthetic studies towards 4,10-diaza-1,7-dioxaspiro[5.5]undecanes: access to 3-aza-6,8-dioxabicyclo[3.2.1]octan-2-one and 2H-1,4-oxazin-3(4H)-one frameworks

Synthetic approaches towards 4,10-diaza-1,7-dioxaspiro[5.5]undecanes starting from 1,3-dichloroacetone and solketal derivatives are explored. The method relies on the preparation of a key bis-substituted dihydroxy-protected oxime, which would undergo a final acidic deprotection-spiroacetalization process. Although the desired diazaspiroketal framework could not be obtained, our conditions led to the unexpected 3-aza-6,8-dioxabicyclo[3.2.1]octan-2-one 18 or to the oxazinone 32 in good yields.

Photochemical cleavage and release of carboxylic acids from α-keto amides

In aqueous media, α-keto amides LGCH2COCON(R)CH(R′) CH3 (1a, R = Et, R′ = H; 1b, R = iPr, R′ = Me; 1c, R = Ph, R′ = H) with various carboxylate leaving groups (LG) at the C-3 position undergo photocleavage and release of carboxylic acids with formation of diastereomeric 5-hydroxyoxazolidin-4-ones 2a,c in the cases of 1a,c or 5-methyleneoxazolidin-4-ones 3b in the case of 1b. For 1a,b, Φ(photocleavage) = 0.24-0.38, whereas Φ(photocleavage) = ca. 0.05 for 1c. The proposed mechanism involves transfer of hydrogen from an N-alkyl group to the keto oxygen to produce zwitterionic intermediates 4a-c that eliminate carboxylate anions. The resultant imminium ions, H2C=C(OH)CON +(R)=C(R′)CH3 5a-c, cyclize intramolecularly to 3b or undergo intermolecular addition of water followed by tautomerization and cyclization to give 2a,c. These inter- or intramolecular trapping reactions of 5 release protons that decrease the pH and cause bleaching of the 620 nm band of the pH indicator, bromocresol green. Determination of the bleaching kinetics by laser flash photolysis methods in the case of 1a gives time constants of 18-137 μs, depending on the leaving group ability of the carboxylate anion, whereas amides 1b show only a small leaving group effect. For 1a, the large leaving group effect is consistent with rate-limiting carboxylate elimination from 4a, whereas the proton release step would be largely rate determining for 1b. Photolyses of 1a (LG = CH3CO2-, PhCH 2CO2-) in neat CH3CN results in carboxylate elimination to form imminium ion 5a, followed by internal return to give aminals.

ARYLPHENYLAMINO-, ARYLPHENYLAMIDE-, AND ARYLPHENYLETHER-SULFIDE DERIVATIVES

The present invention relates in part to compounds of formulas I and III: and pharmaceutically-acceptable salts and prodrugs thereof. These compounds can be useful for treating diseases such as inflammatory and immune diseases. The present invention also relates to pharmaceutical compositions comprising these compounds, and to methods of inhibiting inflammation or suppressing immune response in a subject.

UREA-, GLYCERATE- AND, HYDROXYAMIDE-HEADED HYDROCARBON CHAIN LYOTROPIC PHASES FORMING SURFACTANTS

The invention provides a compound containing a head group based on urea, glycerol or glycerate and a tail selected from the group consisting of a branched alkyl chain, a branched alkyloxy chain or an alkenyl chain. The compounds may be used as surfactants to form a lyotropic phase that is stable in excess polar solution.

A route to homochiral (S)-O-methyl mandelic acid and related α-alkoxy carboxylic acids from isopropylidene glycerol

An improved synthesis of the useful ketones 7 is described. These ketones are then further modified via a highly stereospecific reduction to give homochiral α-alkoxy carboxylic acids which are useful chiral auxiliaries and intermediates.

Reduction of 4-Oxo-α-Amino Acids as a Route to 4-Hydroxylated α-Amino Acids. Concise Approaches to the Synthesis of Clavalanine, erythro-4-Hydroxyornithine and (+)-Bulgecinine

The stereochemical course of reduction of derivatives of 4-oxo-α-amino acids 3 to give cis- and trans-γ-substituted α-aminobutano-4-lactones 9 and 10 using a range of hydride reducing agents is reported.Athough reduction with sodium boranuide (sodium borohydride) in protic solvents proceeds with low stereoselectivity, use of triethylsilane-boron trifluoride-diethyl ether gives good selectivity in favour of the cis-isomer, provided that the 4-substituent is phenyl.Moderate to excellent stereoselectivity in favour of the trans-isomer may be obtained by using L-Selectride in tetrahydrofuran.The presence of an additional stereogenic centre at C-5 completely overwhelms the effect of the α-centre.Applications of this method in approaches to the synthesis of clavalanine, erythro-4-hydroxyornithine and (+)-bulgecinine are described.

N-Acylation of Amino Acids with Glyceric Acid

Several amino acid esters were N-acylated by isopropylidene-D-glyceric acid chloride.The various blocking groups were selectively removed to yield N-D-glyceroyl-amino acids which are able to intra- or intermolecular condensation. - Keywords: N-(O-Isopropy

D-GLYCOPYRANOSYL PHENYLSULPHONES: ACYLATION OF THEIR LITHIATED ANIONS AND REDUCTIVE DESULFONYLATION OF THE RESULTING ACYLATED SULFONES. A SYNTHESIS OF α-D-GLYCOSIDES

The lithiated anion of 3,4,6-tri-O-t-butyldimethylsilyl-2-deoxy-α,β-D-glucopyranosyl phenylsulfone reacts with dimethylcarbonate and various phenyl esters to give stable acylated products.Subsequent reductive lithiation leads to enolates which ungergo kin