5149-49-5

Usage

Type of compound

Diol derivative with a thioether moiety

Usage

Intermediate in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals

Potential applications

Bio-based polymers and plasticizers

Environmental properties

Environmentally friendly

Researched properties

Antimicrobial and antibiotic properties

Value

Versatile and valuable chemical in various industries

Upstream product

• 20256-77-3 2-(benzylsulfanylmethyl)oxirane 
• 96-27-5 rac-3-sulfanylpropane-1,2-diol 
• 100-44-7 benzyl chloride 
• 14007-09-1 2-(2-methoxyphenoxy)-1,3-propanediol 
• 100-53-8 phenylmethanethiol 
• 93-14-1 guaifenesin 

Downstream Products

• 144944-69-4 (2,3-Bis-octyloxy-propylsulfanylmethyl)-benzene 
• 88738-56-1 3-Phenylmethanesulfinyl-propane-1,2-diol 
• 143994-75-6 2-Benzylsulfanylmethyl-1,4,7,10,13-pentaoxa-cyclopentadecane 
• 144944-50-3 rac-1-(benzylsulfanyl)-2,3-bis(octadecyloxy)propane 
• 1415795-32-2 benzyl(2,3-bis((9Z,12Z)-octadeca-9,12-dien-1-yloxy)propyl)sulfane 
• 1278996-66-9 1-(benzylthio)-3-(tert-butyldiphenylsilyloxy)propan-2-ol 
• 1278996-72-7 1-(benzylthio)-3-(tert-butyldiphenylsilyloxy)propan-2-biotinylamide 
• 1278996-71-6 1-(benzylthio)-3-(tert-butyldiphenylsilyloxy)propan-2-amine 
• 1278996-69-2 2-(1-(benzylthio)-3-(tert-butyldiphenylsilyloxy)propan-2-yl)isoindoline-1,3-dione 
• 676245-65-1 C₂₂H₃₈O₄S 
• 146490-99-5 (2-Methoxy-3-octadecyloxy-propylsulfanylmethyl)-benzene 
• 143994-73-4 2-Benzylsulfanylmethyl-1,4,7,10-tetraoxa-cyclododecane 

Relevant academic research and scientific papers

CLEAVABLE LIPIDS

Disclosed herein are novel compounds, pharmaceutical compositions comprising such compounds and related methods of their use. The compounds described herein are useful, e.g., as liposomal delivery vehicles to facilitate the delivery of encapsulated polynucleotides to target cells and subsequent iransfection of said target cells, and in certain embodiments are characterized as having one or more properties that afford such compounds advantages relative to other similarly classified lipids.

Lipopolycationic telomers for gene transfer: Synthesis and evaluation of their in vitro transfection efficiency

We report on the synthesis of a series of lipopolyamine telomers I-14,n, I-18,n, and II-18,n and on their in vitro gene-transfer capability. Their structure consists of a polyamine polar moiety, including n primary amine functions (from 1 to 70), connected to a hydrophobic moiety, including two hydrocarbon C14 or C18 chains, through a mercaptopropanoyl or mercaptoglyceryl unit and an amide or ether function. They were obtained by telomerization of N-{2-[(BOC)-aminoethyl]}acrylamide with N,N-ditetradecyl- and N,N-dioctadecylpropanamide-3-thiol and rac-1,2-dioctadecyloxypropane-3- thiol, respectively, then BOC deprotection. For N/P ratios (N = number of telomer amine equivalents; P = number of DNA phosphates) from 0.8 to 10, these lipopolyamines condensed DNA, with or without the use of DOPE, forming lipopolyplexes or teloplexes of mean sizes less than 200 nm. Some trends, structure-activity and structure-toxicity relationships, were established toachieve both highest in vitro transfection levels and cell viability. Thus, DNA formulations based on telomers I-14,20 and I-18,20 and for N/P ratios lower than 5 led to the most efficient teloplex formulations for plasmid delivery to lung epithelial A549 cells.

Polyamine compounds and compositions containing them useful for the transfer of active substances into a cell

The application relates to polyamine telomer compounds comprising the group of the formula I wherein: A is H or an alkyl of 1 to 4 carbon atoms or an aryl of 5 to 7 carbon atoms, the degree of polymerization n ranges from 1 to 100, R1is selected, independently of one another in each [CH2-CA] nrepeat, from -H, -CH3, -C2H5and - (CH2)u-B, x and u are integers from 2 to 4, B being wherein: y is an integer from 2 to 4, z is an integer from 0 to 6, R3, R4, R5, R6and R7are selected, independently of one another, from H, alkyl or hydroxyalkyl of 1 to 4 carbon atoms.

Facile Synthesis of Thiolariat Ethers or Crown Ethers Containing a Mercapto Group as a Side Arm

Cyclization reaction of S-substituted thioglycerol and oligoethylene glycol ditosylate gave thiolariat ethers in moderate yields.Mercaptomethyl crown ethers were obtained easily from benzylthiomethyl crown ethers by Na in liq.NH3-BuOH.

Synthesis of inositol phospholipids with thiophosphoester bonds

The synthesis of phosphatidylinositol (PI) analogues (±)1-O-(1-O-octadecanoyl-2-O-acetyl-rac-3-thioglycerylphosphoryl)-myo -inositol(7), (±)1-O-(1,2-di-O-octadecyl-rac-3-thioglycerylphosphoryl)-myo-inositol (14a), (±)1-O-(1,2-di-O-octyl-rac-3-thioglycerylphosphoryl)-myo-inositol(14b ) and (±)1-O-(1-O-octadecyl-2-O-methyl-rac-3-thioglycerylphosphoryl)-myo-in ositol(14c) designed to show a novel mode of PI-phospholipase C (PI-PLC) inhibition, is described.

FUNCTIONALLY SUBSITUTED SULFUR-CONTAINING COMPOUNDS. 9. REASTIONS OF 2-OXIRANES WITH ACETIC ANHYDRIDE AND ACETYL CHLORIDE

Reaction of 2-oxiranes with acetic anhydride gives a mixture of 3-(organylthio)-1,2-diacetoxypropane and 2-(organylthio)-1,3-diacetoxypropane, and with acetyl chloride a mixture of 2-chloro-3-(organylthio)-1-acetoxypropane and 3-chloro-2-(organylthio)-1-acetoxypropane.In both cases, the ratio of the isomers depends on the nature of the organylthio group and on the nature of the electrophile.