83526-68-5

Usage

Uses

Used in Organic Synthesis:
(S)-1-O-Benzyl-3-O-trityl-glycerol sol., ~0.5 M in cyclohexane is used as a key intermediate for the synthesis of various organic compounds, particularly in the pharmaceutical and chemical industries. Its unique structure allows for the creation of a wide range of molecules with diverse applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S)-1-O-Benzyl-3-O-trityl-glycerol sol., ~0.5 M in cyclohexane is used as a building block for the development of new drugs and therapeutic agents. Its structural properties enable the design and synthesis of molecules with specific biological activities, targeting various diseases and medical conditions.
Used in Chemical Industry:
(S)-1-O-Benzyl-3-O-trityl-glycerol sol., ~0.5 M in cyclohexane is also utilized in the chemical industry for the production of specialty chemicals, additives, and other materials with specific properties. Its versatility in organic synthesis makes it a valuable component in the development of novel products and applications.

Upstream product

• 56552-80-8 (R)-3-benzyloxy-1,2-propanediol 
• 76-83-5 trityl chloride 
• 136809-12-6 1-(benzyloxy)-3-(trityloxy)propan-2-one 
• 100-39-0 benzyl bromide 
• 16495-03-7 (S)-4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 100-44-7 benzyl chloride 
• 99881-46-6 1-(benzyloxy)-3-(trityloxy)-propan-2-ol 
• 129940-50-7 (S)-tritylglycidol 
• 100-51-6 benzyl alcohol 

Downstream Products

• 96429-71-9 1,2-di-O-benzyl-3-O-triphenylmethyl-sn-glycerol 
• 83542-45-4 3-O-Benzyl-2-O-octadecyl-1-O-trityl-sn-glycerin 
• 172744-76-2 1-O-benzyl-2-O-(2-methoxyethyl)-3-O-tritylglycerol 
• 116953-87-8 3-O-benzyl-2-O-methyl-1-O-trityl-sn-glycerol 
• 1226872-84-9 1-trityl-2-(5'-hexenyl)-3-benzyl-sn-glycerol 
• 941293-70-5 diisopropyl (R)-((((1-benzyloxy)-3-hydroxypropan-2-yl)oxy)methyl)phosphonate 
• 941293-47-6 diisopropyl (S)-(((1-(benzyloxy)-3-(trityloxy)propan-2-yl)oxy)methyl)phosphonate 

Relevant academic research and scientific papers

Novel nucleotide analogues bearing (1H-1,2,3-triazol-4-yl)phosphonic acid moiety as inhibitors of Plasmodium and human 6-oxopurine phosphoribosyltransferases

A novel family of acyclic nucleoside phosphonates (ANPs) bearing a (1H-1,2,3-triazol-4-yl)phosphonic acid group in the acyclic side chain have been prepared in order to study the influence of the hetaryl rigidizing element on the biological properties of

Synthesis and Evaluation of Novel Acyclic Nucleoside Phosphonates as Inhibitors of Plasmodium falciparum and Human 6-Oxopurine Phosphoribosyltransferases

Acyclic nucleoside phosphonates (ANPs) are a promising class of antimalarial therapeutic drug leads that exhibit a wide variety of Ki values for Plasmodium falciparum (Pf) and human hypoxanthine-guanine-(xanthine) phosphoribosyltransferases [HG(X)PRTs]. A novel series of ANPs, analogues of previously reported 2-(phosphonoethoxy)ethyl (PEE) and (R,S)-3-hydroxy-2-(phosphonomethoxy)propyl (HPMP) derivatives, were designed and synthesized to evaluate their ability to act as inhibitors of these enzymes and to extend our ongoing antimalarial structure-activity relationship studies. In this series, (S)-3-hydroxy-2-(phosphonoethoxy)propyl (HPEP), (S)-2-(phosphonomethoxy)propanoic acid (CPME), or (S)-2-(phosphonoethoxy)propanoic acid (CPEE) are the acyclic moieties. Of this group, (S)-3-hydroxy-2-(phosphonoethoxy)propylguanine (HPEPG) exhibits the highest potency for PfHGXPRT, with a Ki value of 0.1 μM and a Ki value for human HGPRT of 0.6 μM. The crystal structures of HPEPG and HPEPHx (where Hx=hypoxanthine) in complex with human HGPRT were obtained, showing specific interactions with active site residues. Prodrugs for the HPEP and CPEE analogues were synthesized and tested for in vitro antimalarial activity. The lowest IC50 value (22 μM) in a chloroquine-resistant strain was observed for the bis-amidate prodrug of HPEPG. Combating malaria: An efficient inhibition of plasmodial 6-oxopurine phosphoribosyltransferase, a key enzyme of the parasitic purine nucleotide salvage pathway, is a promising way to combat malaria. Novel acyclic nucleoside phosphonates were designed as potent inhibitors of phosphoribosyltransferases, and the mode of their binding in the enzyme active site was studied in detail.

OXIDIZED LIPID COMPOUNDS AND USES THEREOF

Novel oxidized lipids are provided herein, as well as methods for producing same, and uses thereof in treating or preventing an inflammation associated with endogenous oxidized lipids and related conditions.

AZACYTOSINE DERIVATIVES USEFUL AS ANTIVIRAL AGENTS

The present invention provides 5-azacytosine derivatives with antiviral activity, specifically having viral replication inhibiting properties, more particularly in DNA viruses such as pox-, papilloma- and herpes viruses in humans. The invention also provi

Univocal syntheses of 2- and 3-hydroxymethyl-2,3-dihydro[1,4]dioxino[2,3-b] pyridine enantiomers

The enantiomers of 2- and 3-hydroxymethyl substituted 2,3-dihydro[1,4] dioxino[2,3-b]pyridine 1 and 2, important chiral building blocks for the preparation of several biologically active compounds, were synthesized. (S)- and (R)-1 were obtained from eithe

Enhanced reactivity of secondary hydroxyl groups in the O-alkylation of carbohydrate-related primary-secondary vic-glycols. Regioselective 2-O-benzylation of 1,3:2,4-di-O-ethylidene-D-glucitol

Partial O-alkylation of 1,3:2,4-di-O-ethylidene-D-glucitol (1a), 1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose (1b), and R-(+)-1-O-benzylglycerol (1c) with benzyl chloride in a KOH/DMSO system results in products of monoalkylation at the secondary (4a-c) and at the primary hydroxyl (2a-c) in ratios of over 95:5 (a), ca. 2:1 (b), and ca. 1:1 (c), whereas (+/-)propane-1,2-diol (1d) gives only the product of 1-O-benzylation (2d).A qualitatively similar result is observed upon O-alkylation of diols (1a-e) with 2-methoxyethanol tosylate.

Synthesis of glyceryl ethers in high optical purity via ruthenium catalyzed asymmetric hydrogenation

1-O-octadecyl-3-O-trityl-glycerol and 1-O-benzyl-3-O-trityl-glycerol can be prepared by asymmetric catalytic hydrogenation in O.P.> 96% and 87-88% respectively.

Biomimetic Studies Using Artificial Systems. II. Enantioselective Thiolysis of D- or L-α-Amino Acid Ester Salts by Thiol-Bearing Chiral Crown Ethers as an Enzyme Model

The rates of transacylation were studied between thiol-bearing chiral crown ethers (1-10) and α-amino acid p-nitrophenyl ester salts.Enantioselectivities, kD/kL ratios, of 6.5 for valine ester salt, 8.7 for phenylalanine ester salt, and 7.7 for valine ester salt were achieved by 1, 5, and 8, respectively.Saturation phenomena of rate acceleration depending on crown concentration were observed and analysis of these data revealed that the chiral recognition occurs in the step of liberation of p-nitrophenol by intra-complex thiolysis, not in the complex-forming step.A possible mechanism for the anantioselectivity is proposed on the basis of the kinetic data.Keywords - crown ether; transacylation; pseudo-first-order rate constant; enantioselectivity; thiolysis; intra-complex reaction; enzyme model

Synthesis and antiherpetic activity of (S)-, (R)- and (±)-9-[(2,3-dihydroxy-1-propoxy)methyl]guanine, linear isomers of 2'-nor-2'-deoxyguanosine

Racemic 9-[2,3-dihydroxy-1-propoxy)methyl]guanine [(±)-iNDG], a new analogue of acyclovir (ACV) and a structural analogue of 2'-nor-2'-deoxyguanosine (2'NDG), was synthesized and found to inhibit the replication of herpes simplex virus types 1 (HSV-1) and 2 (HSV-2). Subsequently, its optical isomers, (R)- and (S)-iNDG, were prepared from chiral intermediates. The chloromethyl ethers of 1,2-di-O-benzyl-D- and -L-glycerol were made and reacted with tris(trimethylsilyl)guanine to give the 9-alkylated guanines, which were deprotected by catalytic hydrogenolysis. Against HSV-1 and HSV-2 in cell culture, (S)-iNDG was approximately 10- to 25-fold more active than the R enantiomer and had an ED50 comparable to those for ACV and 2'NDG. The inferior activity of (R)-iNDG paralleled the poor inhibition of viral DNA polymerase by its phosphorylation products. In mice infected intraperitoneally or orofacially with HSV-1 or intravaginally with HSV-2, (S)-9-[(2,3-dihydroxy-1-propoxy)methyl]guanine [(S)-iNDG] was less efficacious than 2'NDG but comparable to or more active than ACV.