38257-94-2

Usage

Derived from

Butanol (four-carbon alcohol)

Functional group

Triphenylmethoxy (trityl group) attached to the fourth carbon of the butanol chain

Usage

Reagent in organic synthesis, production of pharmaceuticals and specialty chemicals, solvent in organic reactions, and component in cosmetic and personal care product formulation.

Upstream product

• 110-63-4 Butane-1,4-diol 
• 76-83-5 trityl chloride 
• 312493-51-9 (((4-methoxybenzyl)oxy)methanetriyl)tribenzene 
• 431065-45-1 1-methoxy-4-{[4-(trityloxy)butoxy]methyl}benzene 

Downstream Products

• 136424-06-1 4-triphenylmethoxybutanal 
• 1157865-26-3 C₂₃H₂₃FO 
• 1204225-74-0 C₁₉H₂₄O₄ 
• 1082056-35-6 C₃₄H₃₈O₆ 
• 24968-12-5 C₄₂H₄₂O₆ 
• 167103-78-8 4-trityloxybutyric acid 
• 943439-98-3 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-15-trityloxy-pentadec-11(Z)-ene 
• 32293-02-0 4-iodobutyl trityl ether 
• 666698-89-1 methanesulfonic acid 4-trityloxy-butyl ester 

Relevant academic research and scientific papers

Synthesis of trans-2-Substituted Cyclopropylamines from α-Chloroaldehydes

Cyclopropylamines are prevalent in pharmaceuticals and agrochemicals. Herein, we report the synthesis of trans-2-substituted cyclopropylamines in high diastereoselectivity from readily available α-chloroaldehydes. The reaction proceeds via trapping of an electrophilic zinc homoenolate with an amine followed by ring closure to generate the cyclopropylamine. We have also observed that cyclopropylamine cis/trans-isomerization occurs in the presence of zinc halide salts and that this process can be turned off by the addition of a polar aprotic cosolvent.

Cyclic polybutylene terephthalate preparation

The invention specifically discloses a preparation method of novel cyclicpolybutylece terephthalate (PBT) dimer, wherein paraphthaloyl chloride and 1,4-butanediol are used as the raw materials for oriented synthesis of the cyclicpolybutylece terephthalate dimer through a protection and deprotectionstrategy, and the method is used for contrast analysis and detection of cyclicpolybutylece terephthalate dimer impurities in a PBT plastic. The chemical structural formula of the cyclicpolybutylece terephthalate dimer is described in the specification.

Hydrophilic and Cell-Penetrable Pyrrolidinyl Peptide Nucleic Acid via Post-synthetic Modification with Hydrophilic Side Chains

Peptide nucleic acid (PNA) is a nucleic acid mimic in which the deoxyribose-phosphate was replaced by a peptide-like backbone. The absence of negative charge in the PNA backbone leads to several unique behaviors including a stronger binding and salt independency of the PNA-DNA duplex stability. However, PNA possesses poor aqueous solubility and cannot directly penetrate cell membranes. These are major obstacles that limit in vivo applications of PNA. In previous strategies, the PNA can be conjugated to macromolecular carriers or modified with positively charged side chains such as guanidinium groups to improve the aqueous solubility and cell permeability. In general, a preformed modified PNA monomer was required. In this study, a new approach for post-synthetic modification of PNA backbone with one or more hydrophilic groups was proposed. The PNA used in this study was the conformationally constrained pyrrolidinyl PNA with prolyl-2-aminocyclopentanecarboxylic acid dipeptide backbone (acpcPNA) that shows several advantages over the conventional PNA. The aldehyde modifiers carrying different linkers (alkylene and oligo(ethylene glycol)) and end groups (-OH, -NH2, and guanidinium) were synthesized and attached to the backbone of modified acpcPNA by reductive alkylation. The hybrids between the modified acpcPNAs and DNA exhibited comparable or superior thermal stability with base-pairing specificity similar to those of unmodified acpcPNA. Moreover, the modified apcPNAs also showed the improvement of aqueous solubility (10-20 folds compared to unmodified PNA) and readily penetrate cell membranes without requiring any special delivery agents. This study not only demonstrates the practicality of the proposed post-synthetic modification approach for PNA modification, which could be readily applied to other systems, but also opens up opportunities for using pyrrolidinyl PNA in various applications such as intracellular RNA sensing, specific gene detection, and antisense and antigene therapy.

Radical Cyclization Followed by the Fragmentation of Carbonyl Compounds: Effect of an α-Benzoyl Group

To study a recently developed radical cyclization reaction followed by a fragmentation process in more detail, a series of α-benzoyl carbonyl compounds were prepared, including precursors with aldehyde and ketone moieties. Initiated by tributyltin hydride

Influence of the spacer length on the phase behaviors of mesogen-jacketed liquid crystalline polymers with a bulk side-chain

A series of mesogen-jacketed liquid-crystalline polymers (MJLCPs) containing two triphenylmethyl (Tr) units in the side chains, named poly{2,5-bis[(triphenylmethoxy-alkyl)oxycarbonyl]-styrenes} (denoted as Pv-m-Tr, m = 2, 4, 6, 8, 10, 12, which is the num

Facile and selective deprotection of PMB ethers and esters using oxalyl chloride

Oxalyl chloride, (0.5 equiv) was found to cleave the PMB group from alkyl, aryl PMB ethers, and esters to give corresponding alcohol and acid in good yields. This method offers simple and efficient protocol for the selective deprotection of PMB ether and ester in DCE at ambient temperature.

A convenient approach for the deprotection and scavenging of the PMB group using POCl3

A convenient and high yielding approach for the deprotection and scavenging of the p-methoxybenzyl (PMB) group in PMB ethers and PMB esters was developed using POCl3 as the reagent. 4-Methoxybenzyl chloride, a starting material used for the preparation of PMB ethers and esters was regenerated in the deprotection step. This mild and selective procedure tolerates several acid sensitive functional groups. The Royal Society of Chemistry 2013.

Selective cleavage of primary MPM ethers with TMSI/Et3N

A useful method for the selective cleavage of primary MPM ethers by using TMSI/Et3N is described. Other protective groups such as secondary MPM ethers, silyl ethers, and benzylidene acetal were stable under the reaction conditions.

Oligosaccharide synthesis in microreactors

Described is the combination of microreactors and fluorous phase chemistry to assemble oligosaccharides. The synthesis of a β-(1→6) linked D-glucopyranoside homotetramer serves to illustrate this approach. Glycosylations employing a Fmoc-protected glucosy

New Antibacterial Agents Derived from the DNA Gyrase Inhibitor Cyclothialidine

Cyclothialidine (1, Ro 09-1437) is a potent DNA gyrase inhibitor that was isolated from Streptomyces filipinensis NR0484 and is a member of a new family of natural products. It acts by competitively inhibiting the ATPase activity exerted by the B subunit of DNA gyrase but barely exhibits any growth inhibitory activity against intact bacterial cells, presumably due to insufficient permeation of the cytoplasmic membrane. To explore the antibacterial potential of 1, we developed a flexible synthetic route allowing for the systematic modification of its structure. From a first set of analogues, structure-activity relationships (SAR) were established for different substitution patterns, and the 14-hydroxylated, bicyclic core (X) of 1 seemed to be the structural prerequisite for DNA gyrase inhibitory activity. The variation of the lactone ring size, however, revealed that activity can be found among 11- to 16-membered lactones, and even seco-analogues were shown to maintain some enzyme inhibitory properties, thereby reducing the minimal structural requirements to a rather simple, hydroxylated benzyl sulfide (XI). On the basis of these "minimal structures" a modification program afforded a number of inhibitors that showed in vitro activity against Gram-positive bacteria. The best activities were displayed by 14-membered lactones, and representatives of this subclass exhibit excellent and broad in vitro antibacterial activity against Gram-positive pathogens, including Staphylococcus aureus, Streptococcus pyogenes, and Enterococcus faecalis, and overcome resistance against clinically used drugs. By improving the pharmacokinetic properties of the most active compounds (94, 97), in particular by lowering their lipophilic properties, we were able to identify congeners of cyclothialidine (1) that showed efficacy in vivo.