6414-28-4

Upstream product

• 42890-76-6 (S)-1,2,4-butanetriol 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 616-38-6 carbonic acid dimethyl ester 
• 530-62-1 1,1'-carbonyldiimidazole 
• 171110-94-4 4-<(2-benzyloxy)ethyl>-1,3-dioxolan-2-one 
• 102-09-0 bis(phenyl) carbonate 
• 3068-00-6 D,L-1,2,4-butanetriol 
• 57-13-6 urea 
• 19098-31-8 3,4-epoxy-1-butanol 
• 124-38-9 carbon dioxide 
• 201230-82-2 carbon monoxide 

Relevant academic research and scientific papers

Substrate-Controlled Product Divergence: Conversion of CO2 into Heterocyclic Products

Substituted epoxy alcohols and amines allow substrate-controlled conversion of CO2 into a wide range of heterocyclic structures through different mechanistic manifolds. This new approach results in an unusual scope of CO2-derived products by initial activation of CO2 through either the amine or alcohol unit, thus providing nucleophiles for intramolecular epoxy ring opening under mild reaction conditions. Control experiments support the crucial role of the amine/alcohol fragment in this process with the nucleophile-assisted ring-opening step following an SNi pathway, and a 5-exo-tet cyclization, thus leading to heterocyclic scaffolds.

Zinc monoglycerolate as a catalyst for the conversion of 1,3- and higher diols to diurethanes

A green methodology exploring the scope of diurethane synthesis from diols and urea in the presence of a homogeneous catalyst is described. Past reactions of diurethanes have relied heavily on environmentally corrosive reagents such as phosgene. Prior to this work, we have utilized metal glycerolates as homogeneous catalysts in the glycerolysis of urea. Here we explore the synthetic scope of this system with a variety of diols. The conversion to diurethanes is proposed to proceed via an intermediate zinc bound isocyanate ligand, which rearranges to form the terminal urethane in the case of 1,3- and higher diols in good selectivity and yields. With butane 1,2,4-triol the selectivity is exclusively for the 5-membered carbonate, suggesting that the proximity of the second hydroxyl group is critical in forming the ring.

SYNTHESIS OF CYCLIC CARBONATES

The present invention provides a method of synthesizing a cyclic carbonate comprising the step of reacting an alcohol with carbon dioxide.in the presence of a base.

Intramolecular etherification of five-membered cyclic carbonates bearing hydroxyalkyl groups

We report a new one-pot synthetic route to tetrahydrofuran derivatives, which were unexpectedly produced under basic conditions by intramolecular etherification of substituted five-membered cyclic carbonates. For alcohols with vicinal hydroxyl groups, and additional OH groups at the β-position, intramolecular etherification leading to 3-hydroxytetrahydrofuran derivatives was observed. These reactions were studied for compounds having from 2 to 6 hydroxyl groups per molecule, and the mechanism was proposed. The developed method provides a new environmentally friendly approach to the synthesis of five-membered cyclic ether derivatives under non-acidic conditions. The Royal Society of Chemistry.

Monomers containing 2′-O-alkoxymethyl groups as synthons for the oligonucleotide synthesis by the phosphotriester method

A general scheme for the synthesis of ribonucleotides containing an alkoxymethyl group at the 2′-O-position of ribose and an O-nucleophilic catalytic 4-methoxy-1-oxido-2-picolyl phosphate-protecting group has been developed for the introduction into oligonucleotides during their solid-phase synthesis by the phosphotriester method. The scheme has been tested in the synthesis of monomers with 2′-O-modifying groups as examples: 2-azidoethoxymethyl, propargyloxymethyl, and 3,4-cyclocarbonatebutoxymethyl groups.

Palladium-catalyzed carbonylation of diols to cyclic carbonates

The catalytic alkoxycarbonylation of 1,2-diols by (neocuproine) palladium(II) acetate (neocuproine=2,9-dimethyl-1,10-phenanthroline) or palladium(II) acetate/(-)-sparteine using N-chlorosuccinimide as the oxidant affords cyclic carbonates. The oxidative carbonylation of diols proceeds under mild conditions, requiring only 1 atm of carbon monoxide, and produces cyclic carbonates in moderate to good yields. Both 1,2- and 1,3-diols can be carbonylated using (neocuproine)Pd(OAc)2 and sodium dichloroisocyanuric acid, which serves as a competent oxidant and base for this system, to yield 5- and 6-membered cyclic carbonates. Copyright

Synthesis of diether-linked cationic lipids for gene delivery

Quaternary ammonium lipids 1b-d, with diether linkages between hydrocarbon chains and butane or hexane backbone, were synthesized for cationic liposome-mediated gene delivery. The synthetic strategy of using C- 4 or C-6 synthon permits the achievement of the variation of the hydrophobic domain as well as changes of space between the quaternary ammonium head and the hydrophobic domain in the diether-linked cationic lipids.

Regioselective protection of triols to cyclic carbonates

Regioselective protection of 1,2,3-, 1,2,4-, and 1,2,5-triols to 5- membered cyclic carbonates with triphosgene, dimethyl carbonate, or carbonyldiimidazole is described.