59991-89-8

Usage

Physical state

Colorless liquid

Molecular weight

284.35 g/mol

Boiling point

125-127°C

Uses

Solvent, intermediate in the production of other chemicals, corrosion inhibitor, additive in lubricants and oils

Toxicity

Low acute toxicity

Environmental hazard

Not considered a significant hazard

Safety precautions

Handle with care and follow proper safety measures

Upstream product

• 125517-19-3 1,2-di-O-benzyl-3-O-trityl-(R,S)-glycerol 
• 13071-59-5 3-benzyloxypropan-1,2-diol 
• 620-05-3 iodomethylbenzene 
• 41128-90-9 (2S,5R)-5-(benzyloxy)-2-phenyl-1,3-dioxane 
• 100-44-7 benzyl chloride 
• 100-52-7 benzaldehyde 
• 100-39-0 benzyl bromide 
• 68728-34-7 5-benzyloxy-2-phenyl-1,3-dioxane 
• 56-81-5 glycerol 
• 100-51-6 benzyl alcohol 
• 1708-39-0 1,2-benzylideneglycerol 
• 99881-46-6 1-(benzyloxy)-3-(trityloxy)-propan-2-ol 
• 196859-51-5 (2,3-dibenzyloxypropyl) 2,3,4-tri-O-benzyl-α-D-xylopyranoside 
• 1708-40-3 cis-5-hydroxyl-2-phenyl-1,3-dioxane 

Downstream Products

• 96429-72-0 chloromethyl 2,3-di-O-benzyl-L-glyceryl ether 
• 622407-55-0 methanesulfonic acid 2,3-bis-benzyloxy-propyl ester 
• 84245-11-4 1-benzyloxy-3-benzyloxy-2acetyloxymethoxypropane 
• 1065273-80-4 C₂₂H₃₂NO₆P 
• 64350-22-7 Octadecanoic acid 2-[(2,3-bis-benzyloxy-propoxy)-phenylamino-phosphoryloxy]-1-octadecanoyloxymethyl-ethyl ester 
• 71260-19-0 Hexadecanoic acid 2-[(2,3-bis-benzyloxy-propoxy)-(2,2,2-trichloro-ethoxy)-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester 
• 129891-65-2 2,3-di-O-benzyl-D-glycer-1-yl 4,5:7,8-di-O-cyclohexylidene-3-deoxy-N-methyl-α-D-manno-2-octulopyranosidonamide 
• 129870-32-2 2,3-di-O-benzyl-1-O-trifluoromethanesulfonyl-D-glycerol 
• 132119-60-9 1-(2,3-Bis-benzyloxy-propoxymethyl)-4,5-diphenyl-1H-[1,2,3]triazole 
• 132119-64-3 1-(2,3-Bis-benzyloxy-propoxymethyl)-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester 
• 132119-52-9 1-(2,3-Bis-benzyloxy-propoxymethyl)-5-phenyl-1H-[1,2,3]triazole 
• 132119-53-0 1-(2,3-Bis-benzyloxy-propoxymethyl)-4-phenyl-1H-[1,2,3]triazole 
• 119870-10-9 3-(2,3-Bis-benzyloxy-propoxymethyl)-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one 
• 119870-06-3 1-(2,3-Bis-benzyloxy-propoxymethyl)-5-imino-2,5-dihydro-1H-[1,2,3]triazole-4-carboxylic acid amide 

Relevant academic research and scientific papers

Oxylipins arabidopsides C and D from Arabidopsis thaliana

Two new oxylipins, arabidopsides C (1) and D (2), were isolated from the aerial parts of Arabidopsis thaliana, and the structures of 1 and 2 were elucidated using spectroscopic data, primarily NMR and MS, and chemical means. Arabidopsides C (1) and D (2) are rare digalactosyl diacylglycerides containing 12-oxophytodienoic acid and/or dinor-oxophytodienoic acid. Arabidopside D (2) and arabidopsides A (3) and B (4), which were also isolated from this plant, exhibited inhibitory effects on the growth of the root of cress (Lepidium sativum) seedlings at 5 × 10-5 mol/L.

BIPOLAR TETRAETHER LIPIDS

Disclosed herein, inter alia, are compounds, compositions, and liposomes and methods of thereof.

Effect of Headgroups on Small-Ion Permeability across Archaea-Inspired Tetraether Lipid Membranes

This paper examines the effects of four different polar headgroups on small-ion membrane permeability from liposomes comprised of Archaea-inspired glycerolmonoalkyl glycerol tetraether (GMGT) lipids. We found that the membrane-leakage rate across GMGT lipid membranes varied by a factor of ≤1.6 as a function of headgroup structure. However, the leakage rates of small ions across membranes comprised of commercial bilayer-forming 1-palmitoyl-2-oleoyl-sn-glycerol (PO) lipids varied by as much as 32-fold within the same series of headgroups. These results demonstrate that membrane leakage from GMGT lipids is less influenced by headgroup structure, making it possible to tailor the structure of the polar headgroups on GMGT lipids while retaining predictable leakage properties of membranes comprised of these tethered lipids. Extremophiles require robust membranes with low ion permeability to survive in harsh conditions. These Archaea organisms achieve low membrane permeability, in part, by generating lipids with unusual structural features such as tethering of their lipid tails. A systematic study probing the effect of polar headgroups in synthetic Archaea-inspired lipids showed little dependence of membrane leakage rates of small ions as a function of headgroup structure.

Glycerol etherification with benzyl alcohol over sulfated zirconia catalysts

Glycerol (GLY) etherification with benzyl alcohol (BA) was conducted with different zirconia-based heterogeneous acid catalysts, aiming to produce mono- (ME) and dibenzyl glycerol ethers (DE). Physicochemical properties of the prepared catalysts were obtained through XRD, SEM and adsorption of ammonia. The catalytic tests were performed at different temperatures (120-140°C) and initial reactant mass ratios (GLY:BA 1:1 and 2:1). The highest BA conversions were obtained with the catalyst having the highest sulfuric acid content (2S/ZrO2). An increase in the reaction temperature and the GLY:BA initial mass ratio led to an increase in the BA conversion. Two kinetic models (a potential and a hyperbolic approach) were proposed to describe the process performance, including not only reactants evolution with time, but also that of ME, DE and the undesired self-condensation product of BA (benzyl ether, BE). Kinetic parameters for each model were estimated by data fitting and both models were able to accurately describe the evolution of the system, in terms of reactants and product distribution as a function of time under the experimental conditions studied.

Parallel synthesis and antileishmanial activity of ether-linked phospholipids

The synthesis and antileishmanial activity of 18 edelfosine analogues are described. Compounds were obtained in parallel combining solid phase and solution phase synthesis. The most active analogue is characterized by the octadecyl group in position 2 of the glycerol chain. Considering that this substitution determines the loss of antitumor activity, a different mechanism of antileishmanial action can be hypothesized.

Binding of tetramethylammonium to polyether side-chained aromatic hosts. Evaluation of the binding contribution from ether oxygen donors

A set of macrocyclic and open-chain aromatic ligands endowed with polyether side chains has been prepared to assess the contribution of ether oxygen donors to the binding of tetramethylammonium (TMA), a cation believed incapable of interacting with oxygen donors. The open-chain hosts consisted of an aromatic binding site and side chains possessing a variable number of ether oxygen donors; the macrocyclic ligands were based on the structure of a previously investigated host, the dimeric cyclophane 1,4-xylylene-1,4-phenylene diacetate (DXPDA), implemented with polyether-type side chains in the backbone. Association to tetramethylammonium picrate (TMAP) was measured in CDCl 3 at T = 296 K by 1H NMR titrations. Results confirm that the main contribution to the binding of TMA comes from the cation - π interaction established with the aromatic binding sites, but they unequivocally show that polyether chains participate with cooperative contributions, although of markedly smaller entity. Water is also bound, but the two guests interact with aromatic rings and oxygen donors in an essentially noncompetitive way. An improved procedure for the preparation of cyclophanic tetraester derivatives has been developed that conveniently recycles the oligomeric ester byproducts formed in the one-pot cyclization reaction. An alternative entry to benzylic diketones has also been provided that makes use of a low-order cyanocuprate reagent to prepare in fair yields a class of compounds otherwise uneasily accessible.

Differential cleavage of arylmethyl ethers: Reactivity of 2,6-dimethoxybenzyl ethers

CrCl2/LiI selectively cleave benzyl ethers and methoxy-substituted benzyl ethers (see scheme) in the order: C6H5CH2OR 6H4CH2OR 2C6H3CH2OR 2C6H3CH2OR. In contrast, C6H5CH2OR is more readily cleaved than 2,6-(MeO)2C6H3CH2OR during catalytic hydrogenolysis while 3,4-(MeO)2C6H3CH2OR is cleaved faster than 2,6-(MeO)2C6H3CH2OR with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).

Molecular dynamics-based models explain the unexpected diastereoselectivity of the sharpless asymmetric dihydroxylation of allyl D- xylosides

The catalytic asymmetric dihydroxylation of several allyl 2-O-benzyl-α- D-xylosides with AD-mix β and PYR(DHQD)2 shows almost no diastereofacial selectivity if the 3- and 4-OH groups are unprotected or acetylated. Acetal, benzyl ethers and benzoyl esters enhance the diastereoselectivity, in the opposite sense to that predicted by the 'AD mnemonic', which is completely lost using AD-mix α. In an attempt to understand this behaviour, computational studies of the asymmetric dihydroxylation (AD) of olefins using Sharpless' and Corey's catalysts have been carried out using molecular dynamics. A three-step algorithm was developed taking advantage of the enzyme-like behaviour of catalyst-olefin systems and applied using an ESFF force field. To validate our approach, the first sampling step procedure was then refined and performed using a modified CVFF force field. This led to a U-shaped model in good agreement with that proposed by Corey for the AD of allyl 4-methoxybenzoates, which brings to the fore a role for the methoxy group. This model also accounts for the observed enantioselectivity of styrene dihydroxylation. When applied to the AD of allyl xylosides using AD- mix β, our model accounts well for the observed diastereoselectivity. Both synthetic and modelling results confirmed that aromatic groups on the olefin could be involved in π-π stacking interactions with the aromatic rings of the catalyst and should be important, if not a prerequisite, to achieve high enantio- and diastereoselectivity.

Selective monoalkylation of acyclic diols by means of dibutyltin oxide and fluoride salts

Fluoride anion was found to promote monoalkylation reaction of diols by the stannylene acetal method, and selective monoalkylation of various acyclic diols was accomplished in good yields under mild conditions by employing this new method. Functional groups such as carboxylic acid ester, carboxamide, carbamate, nitrile, alkyl chloride, and ether were not affected under the reaction conditions.