16354-95-3

Usage

Uses

Used in Pharmaceutical Industry:
[S(R,R)]-1-phenylglycerol is used as an intermediate for the synthesis of various pharmaceuticals and fine chemicals. Its chiral properties allow for the creation of specific drug molecules with desired stereochemistry, which can significantly impact the drug's efficacy and safety.
Used in Asymmetric Synthesis:
In the field of organic chemistry, [S(R,R)]-1-phenylglycerol serves as a chiral auxiliary, aiding in the asymmetric synthesis of complex molecules. This application is crucial for the development of enantiomerically pure compounds, which are essential in the pharmaceutical industry to ensure the desired biological activity and minimize potential side effects.
Used in Organic Synthesis:
[S(R,R)]-1-phenylglycerol is also utilized as a chiral reagent in organic synthesis, where it can influence the stereochemistry of reactions, leading to the formation of specific enantiomers. This ability is particularly important in the synthesis of biologically active molecules, as the stereochemistry of a compound can greatly affect its interactions with biological targets.

InChI:InChI=1/C9H12O3/c10-6-8(11)9(12)7-4-2-1-3-5-7/h1-5,8-12H,6H2

Upstream product

• 16354-91-9 (S)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl](phenyl)methanol 
• 4510-34-3 (Z)-cinnamyl alcohol 
• 14371-10-9 (E)-3-phenylpropenal 
• 98819-68-2 3-phenyl-(2R,3R)-oxiran-2-ylmethanol 
• 5792-35-8 2,3-dihydroxy-1-phenylpropan-1-one 
• 7732-18-5 water 
• 64-17-5 ethanol 
• 162599-28-2 (1S:2R)-1.2.3-tribenzoyloxy-1-phenyl-propane 
• 40641-81-4 trans-2,3-epoxy-3-phenylpropan-1-ol 
• 121651-02-3 (2S,3R)-2-formyl-3-phenyloxirane 
• 121802-28-6 (R)-4-((S)-Hydroxy-phenyl-methyl)-[1,3]dioxolan-2-one 
• 110379-48-1 (R)-(R)-[1,3]Dioxolan-4-yl-phenyl-methanol 
• 21915-53-7 cis-2,3-epoxy-3-phenyl-1-propanol 
• 110379-53-8 [1,3]Dioxolan-4-yl-phenyl-methanone 

Downstream Products

• 859185-40-3 2-(4-nitro-phenyl)-4-phenyl-[1,3]dioxan-5-ol 
• 16354-94-2 C₃₀H₂₄O₆ 
• 16354-94-2 (1RS,2RS)-1,2,3-tris-benzoyloxy-1-phenyl-propane 
• 859935-23-2 5-methoxy-2-(4-nitro-phenyl)-4-phenyl-[1,3]dioxane 
• 26151-12-2 (2,2-dimethyl-[1,3]dioxolan-4-yl)-phenyl-methanol 
• 859813-98-2 (2,2-dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-methanol 
• 86551-93-1 (2S)-3-phenyl-propane-1,2-diol diacetate 
• 17131-14-5 (S)-(-)-3-phenyl-1,2-propanediol 
• 86594-56-1 (1S,2R)-1-phenyl-1,2,3-triacetoxypropane 

Relevant academic research and scientific papers

An ingenious method for the determination of the relative and absolute configurations of compounds containing aryl-glycerol fragments by1H NMR spectroscopy

A concise method was established to determine the relative and absolute configurations of aryl-glycerols that depend on the chemical shift differences (Δδ) of the diastereotopic methylene protons (H-3) by1H NMR spectroscopy. When using DMSO-d6as the preferred solvent, thethreoconfiguration corresponded to a larger ΔδH3a-H3bvalue (>0.15 ppm), whereas theerythroconfiguration (a smaller value. Furthermore, the absolute configurations were determined with the aid of a simple acylation reaction through camphanoyl chloride. In thethreoenantiomers, the Δδvalue of the 1R,2Rconfiguration was 0.20 ppm. In theerythroenantiomers, the Δδvalue of 1R,2Swas >0.09 ppm, and that of 1S,2Rwas 3. In addition, this method was also verified by a quantum1H NMR calculation.

Molybdenum-Catalyzed Hydroxyl-Directed Anti-Dihydroxylation of Allylic and Homoallylic Alcohols

A catalytic hydroxyl-directed anti-dihydroxylation of allylic and homoallylic alcohols has been developed. This operationally simple method was successfully applied to the direct anti-monodihydroxylation of allylic alcohols containing at least one distal olefinic unit. Under the catalysis of commercially available MoO2(acac)2, an array of hydroxylated dienes were successfully converted into various 1,2,3-triols using hydrogen peroxide as an environmentally benign oxidant under aerobic conditions, notably, in complete regioselectivities and in the most cases in diastereospecific pathway.

Expedient synthesis of C-aryl carbohydrates by consecutive biocatalytic benzoin and aldol reactions

The introduction of aromatic residues connected by a C-C bond into the non-reducing end of carbohydrates is highly significant for the development of innovative structures with improved binding affinity and selectivity (e.g., C-aril-sLex). In this work, an expedient asymmetric de novo synthetic route to new aryl carbohydrate derivatives based on two sequential stereoselectively biocatalytic carboligation reactions is presented. First, the benzoin reaction of aromatic aldehydes to dimethoxyacetaldehyde is conducted, catalyzed by benzaldehyde lyase from Pseudomonas fluorescens biovar I. Then, the a-hydroxyketones formed are reduced by using NaBH4 yielding the anti diol. After acetal hydrolysis, the aldol addition of dihydroxyacetone, hydroxyacetone, or glycolaldehyde catalyzed by the stereocomplementary d-fructose-6-phosphate aldolase and l-rhamnulose-1-phosphate aldolase is performed. Both aldolases accept unphosphorylated donor substrates, avoiding the need of handling the phosphate group that the dihydroxyacetone phosphatedependent aldolases require. In this way, 6-C-aryl-l -sorbose, 6-C-aryl-l-fructose, 6-C-aryl- l-tagatose, and 5-C-aryl-l-xylose derivatives are prepared by using this methodology.

Organocatalytic asymmetric synthesis of 1,2,3-prim,sec,sec-triols

A tandem organocatalytic asymmetric synthesis of 1,2,3-triols using a,b-unsaturated aldehydes as the substrates and hydrogen peroxide as the oxidant is presented. The reaction can also be applied to the asymmetric synthesis of 3-chloro-1,2-propandiols. Georg Thieme Verlag Stuttgart.

The 1H NMR method for the determination of the absolute configuration of 1,2,3-prim,sec,sec-triols

The absolute configuration of 1,2,3-prim,sec,sec-triols can be assigned by comparison of the 1H NMR spectra of the tris-(R)- and the tris-(S)-MPA ester derivatives. An experimental demonstration of this correlation with 24 triols of known absolute configuration and a protocol using two parameters-ΔδRS(H3) and the difference between ΔδRS(H2) and ΔδRS(H3) = |Δ(ΔδRS)|-for its application to the determination of the absolute configuration of other triols are presented.

The asymmetric dihydroxylation of cis-allylic and homoallylic alcohols

The asymmetric dehydroxylation of several cis allylic alcohols is reported. The reactions proceed with moderate to good enantioselectivity. The enhanced enantioselection observed relative to other cis-olefin classes is believed to be dependent on the presence of the free hydroxyl group. A cis-homoallylic alcohol also gave a useful level of enantioselection in the AD.

DIRECT TRANSFORMATION OF 2,3-EPOXY ALCOHOLS INTO HYDROXY CARBONATES UNDER MILDLY BASIC CONDITIONS

2,3-Epoxy alcohols are transformed into the corresponding C2-inverted hydroxy carbonates upon treatment with cesium carbonate-powdered 3-Angstroem molecular sieves in N,N-dimethylformamide under one atmosphere of carbon dioxide at 23-78 deg C.

CYCLOFUNCTIONALISATION OF EPOXYALCOHOL DERIVATIVES. 2. STEREO- AND REGIOSPECIFIC CONVERSION TO 1,3-DIOXOLANES

2,3-Epoxyalcohols react with paraformaldehyde and either cesium carbonate or potassium carbonate/phase-transfer catalyst in polar, aprotic solvents to give excellent yields of 4-(1-hydroxyalkyl)-1,3-dioxolanes, with inversion at C-2.