13754-10-4

Usage

InChI:InChI=1/C14H18O5/c1-11(15)18-10-14(19-12(2)16)9-17-8-13-6-4-3-5-7-13/h3-7,14H,8-10H2,1-2H3

Upstream product

• 13071-59-5 3-benzyloxypropan-1,2-diol 
• 64-19-7 acetic acid 
• 108-05-4 vinyl acetate 
• 151121-12-9 acetic acid 2-acetoxy-3-benzyloxy-propyl ester 
• 4152-39-0 1-O-acetyl-3-O-benzylpropane-1,2,3-triol 
• 56552-80-8 (R)-3-benzyloxy-1,2-propanediol 
• 75-36-5 acetyl chloride 
• 17325-85-8 (2S)-3-(benzyloxy)propane-1,2-diol 
• 108-24-7 acetic anhydride 
• 14618-80-5 (R)-benzyl glycidol 
• 100-44-7 benzyl chloride 
• 244056-60-8 (2R,6S,7S,9R,14S)-14-Benzyloxymethyl-2,9-bis(hydroxymethyl)-1,8,13,16-tetraoxadispiro<5.0.5.4>hexadecane 
• 153214-79-0 1-(benzyloxy)-3-hydroxypropan-2-one 
• 40166-30-1 3-(benzyloxy)-2,2-dimethoxypropan-1-ol 

Downstream Products

• 17325-87-0 (2R)-1,2-diacetoxy-3-(benzyloxy)propane 

Relevant academic research and scientific papers

Remarkable functions of sn-3 hydroxy and phosphocholine groups in 1,2-diacyl-sn-glycerolipids to induce clockwise (+)-helicity around the 1,2-diacyl moiety: Evidence from conformation analysis by 1H NMR spectroscopy

Cell-membrane glycerolipids exhibit a common structural backbone of asymmetric 1,2-diacyl-sn-glycerol bearing polar head groups in the sn-3 position. In this study, the possible effects of sn-3 head groups on the helical conformational property around the 1,2-diacyl moiety in the solution state were examined. 1H NMR Karplus relation studies were carried out using a series of 1,2-dipalmitoyl-sn-glycerols bearing different sn-3 substituents (namely palmitoyl, benzyl, hydrogen, and phosphates). The 1H NMR analysis indicated that the helical property around the 1,2-diacyl moiety is considerably affected by these sn-3 substituents. The sn-3 hydroxy group induced a unique helical property, which was considerably dependent on the solvents used. In CDCl3 solution, three staggered conformers, namely gt(+), gg(?) and tg, were randomized, while in more polar solvents, the gt(+) conformer with (+)-helicity was amplified at the expense of gg(?) and tg conformers. The sn-3 phosphocholine in phosphatidylcholine exhibited a greater effect on the gt(+) conformer, which was independent of the solvents used. From the 1H NMR analysis, the helical conformational properties around the 1,2-diacyl moiety conformed to a simple empirical rule, which permitted the proposal of a conformational diagram for 1,2-dipalmitoyl-sn-glycerols in the solution states.

Aerobic Acetoxyhydroxylation of Alkenes Co-catalyzed by Organic Nitrite and Palladium

An aerobic acetoxyhydroxylation of alkenes cooperatively catalyzed by organic nitrite and palladium at room temperature using clean and cheap air as the sole oxidant has been developed. Various vicinal diols, diacetoxyalkanes, and dihalogenoalkanes have been synthesized. The gram-scale synthesis has also been approached. Vicinal difluorination and dichlorolation products have also been achieved via this reaction.

Aerobic palladium-catalyzed dioxygenation of alkenes enabled by catalytic nitrite

Catalytic nitrite was found to enable carbon-oxygen bond-forming reductive elimination from unstable alkyl palladium intermediates, providing dioxygenated products from alkenes. Avariety of functional groups were tolerated, and high yields (up to 94%) were observed with many substrates, also for a multigram-scale reaction. Nitrogen dioxide, which could form from nitrite under the reaction conditions, was demonstrated to be a potential intermediate in the catalytic cycle. Furthermore, the reductive elimination event was probed with 18O-labeling experiments, which demonstrated that both oxygen atoms in the difunctionalized products were derived from one molecule of acetic acid.

BF3·OEt2-promoted diastereoselective diacetoxylation of alkenes by PhI(OAc)2

Selective syn and anti diacetoxylations of alkenes have been achieved using a PhI(OAc)2/BF3·OEt2 system in the presence and absence of water, respectively. A broad range of substrates including electron-deficient alkenes (such as α,β-unsaturated esters) could be elaborated efficiently at room temperature with this methodology, furnishing the desired products in good to excellent yields and diastereoselectivity. In particular, a multigram-scale diastereoselective diacetoxylation of methyl cinnamate (5.00 g) was also accomplished in a few hours, maintaining the same efficiency as small-scale reaction. This novel methodology provides an alternative approach for the preparation of various 1,2-diols.

Palladium-catalyzed olefin dioxygenation

A general method for the vicinal dioxygenation of olefins was developed using cationic Pd diphosphine complexes as the catalysts and PhI(OAc)2 as the terminal oxidant. In comparison to known Pd-catalyzed vicinal oxidations, this method is suitable for a broad range of olefins in both inter- and intramolecular reactions. An 18O-labeling experiment provides insight into the mechanism of this transformation which presumably involves Pd(II)/Pd(IV) intermediates. Copyright

Lipid-improving agent and composition containing lipid-improving agent

A lipid-improving agent containing a triglyceride(s) where a poly-unsaturated fatty acid is bonded to 2-position of a triglyceride(s).

Efficient chemoenzymatic enantioselective synthesis of diacylglycerols (DAG)

A new efficient chemoenzymatic methodology for the production of 3-O-benzyl-sn-glycerol and 1,2-O-dipalmitoyl-sn-glycerol has been developed. It starts from racemic 1-O-benzylglycerol and is based on the sequential enzymatic acylation-Mitsunobu inversion-enzymatic hydrolysis, which has been performed without isolation of the intermediates. In this way a 70-75% yield of 3-O-benzyl-sn-glycerol with 94-96% ee has been obtained.

Dispiroketals in synthesis. Part 24. Preparation and use of chiral 2,2′-bis(triisopropylsilyloxymethyl)bi(dihydropyran)s as new protecting and resolving agents for 1,2-diols

C2 symmetric chiral 2,2′-bis(triisopropylsilyloxymethyl)bi(dihydropyran)s (S,S)-1 and (R,R)-1 were prepared from the corresponding glycidols and selectively reacted with 1,2-diols to give dispiroketals. The products of these reactions could be deprotected following treatment with fluoride, oxidation and reductive cleavage with samarium(II) iodide.

Baker's yeast mediated reduction of dihydroxyacetone derivatives

Several monoprotected dihydroxyacetone derivatives 4a-d and their acetates 5a-d were prepared and subjected to biotransformation with baker's yeast. The simple chemical modification of the substrates (i.e. transforming the relatively small hydrophilic hyd