70259-44-8

Usage

Uses

Used in Organic Synthesis:
(2S)-1-(benzyloxy)-3-(trityloxy)propan-2-ol serves as a protecting group in organic synthesis, where it is utilized to prevent undesired reactions from occurring at particular sites on a molecule. This function is crucial for the selective synthesis of complex organic compounds, ensuring that reactions proceed with the desired specificity and yield.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (2S)-1-(benzyloxy)-3-(trityloxy)propan-2-ol may find applications due to its unique structural features. The presence of the benzyloxy and trityloxy groups could potentially allow for the development of new pharmaceutical agents or the modification of existing ones, enhancing their efficacy, selectivity, or stability.
Used in Chemical Research:
(2S)-1-(benzyloxy)-3-(trityloxy)propan-2-ol's distinct spatial arrangement and functional groups make it a valuable tool in chemical research. It can be employed to study the effects of stereochemistry on molecular interactions, reaction mechanisms, and the properties of compounds, contributing to a deeper understanding of chemical processes and the development of novel chemical entities.

Upstream product

• 56552-80-8 (R)-3-benzyloxy-1,2-propanediol 
• 76-83-5 trityl chloride 
• 17325-85-8 (2S)-3-(benzyloxy)propane-1,2-diol 
• 136809-12-6 1-(benzyloxy)-3-(trityloxy)propan-2-one 
• 83526-68-5 (S)-1-(benzyloxy)-3-trityloxypropan-2-ol 
• 65291-30-7 (R)-(+)-trityl glycidyl ether 
• 20194-18-7 sodium phenyl-methanolate 
• 14347-83-2 (R)-2,2-dimethyl-4-benzoxymethyl-1,3-dioxolane 
• 100-39-0 benzyl bromide 
• 100-51-6 benzyl alcohol 
• 99881-46-6 1-(benzyloxy)-3-(trityloxy)-propan-2-ol 
• 872202-29-4 (S)-1-O-benzyl-2-O-mesyl-3-O-tritylglycerol 

Downstream Products

• 154023-30-0 1-benzyl-2-hexadecyl-3-trityl-sn-glycerol 
• 222984-12-5 3-O-trityl-2-O-(R)-citronellyl-1-O-benzyl-sn-glycerol 
• 154098-03-0 1-benzyl-2-hexadecyl-sn-glycerol 
• 1182357-79-4 (S)-1-Benzyloxy-2-fluoro-3-trityloxypropane 

Relevant academic research and scientific papers

Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision**

Crenarchaeol is a glycerol dialkyl glycerol tetraether lipid produced exclusively in Archaea of the phylum Thaumarchaeota. This membrane-spanning lipid is undoubtedly the structurally most sophisticated of all known archaeal lipids and an iconic molecule in organic geochemistry. The 66-membered macrocycle possesses a unique chemical structure featuring 22 mostly remote stereocenters, and a cyclohexane ring connected by a single bond to a cyclopentane ring. Herein we report the first total synthesis of the proposed structure of crenarchaeol. Comparison with natural crenarchaeol allowed us to propose a revised structure of crenarchaeol, wherein one of the 22 stereocenters is inverted.

Diverse synthetic approaches towards C1′-branched acyclic nucleoside phosphonates

Acyclic nucleoside phosphonates (ANPs) represent a significant class of antiviral, anticancer, and antiprotozoal compounds. It is therefore highly desirable to have diverse synthetic routes leading towards these molecules. In the past, many structural modifications were explored, but surprisingly, the field of C1′-branched ANPs has been neglected with only a handful of articles reporting their synthesis. Herein we describe and compare five convenient approaches leading to key synthetic 6-chloropurine ANPs bearing the 9-phosphonomethoxyethyl (PME) moiety branched at the C1′ position. These intermediates can be further vastly diversified into target C1′-branched ANPs bearing either natural or unnatural nucleobases. The importance of C1′-branched ANPs is emphasized by their analogy with C1′-substituted cyclic nucleotides (such as remdesivir, a broad-spectrum antiviral agent) and evaluation of their biological activity (e.g. antiviral, antineoplastic, and antiprotozoal) will be a tempting subject of further research.

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.

Acyclic nucleoside phosphonates with 5-azacytosine base moiety substituted in C-6 position

Two methods for preparation of 6-substituted derivatives of anti DNA-viral agent 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]-5-azacytosine (HPMP-5-azaC) were developed: (1) ammonia mediated ring-opening reaction of diisopropyl esters of HPMP-5-azaC (4) t

Synthesis of archaeal bipolar lipid analogues: A way to versatile drug/gene delivery systems

(Chemical Equation Presented) A synthetic route for the preparation of symmetrical and unsymmetrical archaeal tetraether-like analogues has been described. The syntheses are based upon the elaboration of hemimacrocyclic tetraether lipid cores from versati

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

Synthesis of 1-palmitoyl-2-hexadecyl-sn-glycero-3-phospholine (PHPC)

A general method for the chirospecific synthesis of 1-acyl-2-alkyl-sn-glycero-3-phosphocholines is described. 1-Palmityl-2-hexadecyl-sn-glycero-3-phosphocholine (PHPC) was synthesized in 18percent overall yield in ten steps via five new synthetic intermediates, and 1-acetyl-2-hexadecyl-sn-glycero-3-phosphocholine (AHPC) was also synthesized. 1-Acetyl-2-alkyl-sn-glycero-3-phosphocholines, which have not been found to exist in nature, are ether lipid analogs of 1,2-diacetyl-sn-glycero-3-phosphocholines, which are important components of cell membranes.Biophysical studies of hydrated bilayers of PHPC will be of interest in probing the critical importance of the central region of these amphiphilic molecules to the molecular assemblies that are found. Key words: 1-Acetyl-2-alkyl-sn-glycero-3-phosphocholine; 1-Palmitoyl-2-hexadecyl-sn-glycero-3-phosphocholine; PHPC; 1-acetyl-2-hexadecyl-sn-glycero-3-phosphocholine; AHPC; Palmitic anhydride

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.