124649-67-8

Usage

Uses

Used in Pharmaceutical Industry:
METHYL (2S,3R)-(-)-2,3-DIHYDROXY-3-PHENYLPROPIONATE is used as a key intermediate for the preparation of taxol side chain. It plays a crucial role in the synthesis of the anticancer drug Taxol, which is used to treat various types of cancer, including ovarian, breast, and lung cancer.
Additionally, it can be used to synthesize methyl(2R,3R)-2,3-epoxy-3-phenylpropionate, another important intermediate in the production of pharmaceuticals and organic compounds. METHYL (2S,3R)-(-)-2,3-DIHYDROXY-3-PHENYLPROPIONATE can be further utilized in the development of new drugs and materials with potential applications in various industries.

InChI:InChI=1/C10H12O4/c1-14-10(13)9(12)8(11)7-5-3-2-4-6-7/h2-6,8-9,11-12H,1H3/t8-,9+/m1/s1

Upstream product

• 103-26-4 Methyl cinnamate 
• 67-56-1 methanol 
• 81691-59-0 (2RS,3RS)-2,3-dihydroxy-3-phenyl-propionic acid methyl ester 
• 100-52-7 benzaldehyde 
• 18020-59-2 methyl 3-hydroxy-2-methylidene-3-phenylpropionate 
• 119096-73-0 methyl 3-hydroxy-2-oxo-3-phenylpropionate 
• 19190-80-8 methyl trans-3-phenylglycidate 
• 103-26-4 methyl cinnamate 
• 186581-53-3 diazomethane 
• 55449-79-1 (2S,3R)-2,3-dihydroxy-3-phenyl-propionic acid 
• 133520-54-4 (-)-2,3-dihydroxy-3-phenylpropanenitrile 
• 133520-55-5 2,2-Dimethyl-5-phenyl-1,3-dioxolan-4-carbonitril 
• 133520-53-3 2,3-Dihydroxy-3-phenylpropannitril 
• 133520-56-6 2,2-Dimethyl-5-phenyl-1,3-dioxolan-4-carbonitril 

Downstream Products

• 124605-43-2 (2S,3R)-(-)-methyl 3-hydroxy-3-phenyl-2-((p-tolylsulfonyl)oxy)propionate 
• 1027419-66-4 (2S,3R)-2,3-Dimethoxy-3-phenyl-propionic acid methyl ester 
• 1422559-80-5 (R)-5-((S)-((4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)(hydroxy)methyl)furan-2(5H)-one 
• 1422559-82-7 (S)-5-((S)-((4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)(hydroxy)methyl)furan-2(5H)-one 
• 1422559-83-8 (S)-((4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)((R)-5-oxo-2,5-dihydrofuran-2-yl)methyl acetate 
• 1422559-84-9 (S)-((4S,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)((S)-5-oxo-2,5-dihydrofuran-2-yl)methyl acetate 
• 1422559-73-6 (E)-5-(((4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl)methylene)furan-2(5H)-one 
• 918906-87-3 8-epi-crassalactone D 
• 1422559-76-9 (5R,7R,8S,9S)-9-bromo-8-hydroxy-7-phenyl-1,6-dioxaspiro[4.4]non-3-en-2-one 
• 16354-93-1 (1RS,2SR)-1-phenyl-propane-1,2,3-triol 

Relevant academic research and scientific papers

Dihydroxylation of Olefins with Potassium Permanganate Catalyzed by Imidazolium Salt

The development of an efficient and cost-effective cis -dihydroxylation reaction of acrylate derivatives was achieved. The reaction proceeded in acetone with an imidazolium salt as catalyst to furnish the dihydroxylation of olefins at 0-5 °C using KMnO 4 as the oxidant. This efficient and non-aqueous protocol was highly suitable for the large-scale preparation of cis -dihydroxylated compounds from the corresponding acrylate derivatives in high yields without overoxidation.

Asymmetric dihydroxylation catalyzed by ionic polymer-supported osmium tetroxide

Osmium tetroxide was immobilized onto a short-length PEGylated ionic polymer, which exhibited excellent catalytic performance in OsO4-catalyzed asymmetric dihydroxylation. The resulting polymer was recycled five times without any loss of yield or enantioselectivity. In addition to the immobilization of osmium, the polymer also exhibited an ability to immobilize a significant amount of chiral ligand.

A triazine core for a new class of Sharpless asymmetric dihydroxylation ligands

Sharpless asymmetric dihydroxylation ligands were synthesized using a triazine spacer group in two, high yielding steps and gave good enantioselectivities in the asymmetric dihydroxylation of alkenes. Sharpless asymmetric dihydroxylation ligands were synthesized using a triazine spacer group in two, high yielding steps from cheap, readily available starting materials. The ligands, gave good enantioselectivities in the asymmetric dihydroxylation of alkenes and may provide a very economic alternative to current systems.

MTO and OsO4: An efficient catalytic couple for mild H2O2-based asymmetric dihydroxylation of olefins

A novel and robust system for osmium-catalyzed asymmetric dihydroxylation of olefins by aqueous H2O2 with methyltrioxorhenium (MTO) as electron transfer mediator (ETM) has been developed. The MTO is catalyzing the H2O2 oxidation of the chiral ligand to its mono-N-oxide, which in turn reoxidizes OsVI to OsVIII. Thus the (DHQD)2PHAL plays a dual role serving as the chiral inductor as well as the tertiary amine generating the N-oxide required for the recycling of osmium. The present catalytic system gives vicinal diols in good isolated yields and high enantiomeric excess (up to 99 % ee).

Silica Gel-Supported Cinchona Alkaloid-OsO4 Complex for Catalytic Heterogeneous Asymmetric Dihydroxylation of Olefins by H2O2 using a Titanium Silicalite-Based Coupled Catalytic System

A triple catalytic system designed for asymmetric dihydroxylation of olefins, composed of NMM and two divergent heterogeneous catalysts, titanium silicalite and silica gel-supported 1,4-bis(9-O-dihydroquinidinyl)phthalazine [SGS-(DHQD)2 PHAL)]-OsO4 complex relays the transport of two electrons from olefin to H2O2 used as a terminal oxidant to provide chiral diols with good yields and high enantiomeric excesses in a single pot.

Asymmetric dihydroxylation of olefins using cinchona alkaloids on highly ordered inorganic supports

(matrix presented) A modified cinchona alkaloid was grafted onto a mesoporous molecular sieve and onto amorphous silica gel. These heterogeneous ligands were employed in the asymmetric dihydroxylation of olefins under Sharpless conditions. The supported ligands yielded equivalent enantioselectivity compared with that of the homogeneous system and were easily recovered and reused.

SULFAMATE DERIVATIVE COMPOUNDS FOR USE IN TREATING OR ALLEVIATING A PSYCHIATRIC DISORDER

The present invention relates to a pharmaceutical composition for treating and/or alleviating a psychiatric disorder comprising a sulfamate derivative compound and/or a pharmaceutically acceptable salt thereof as an active ingredient. Furthermore, the present invention relates to a pharmaceutical composition for inducing anti-stress, anti-anxiety and/or anti-depressant activities comprising a sulfamate derivative compound and/or a pharmaceutically acceptable salt thereof as an active ingredient.

Racemic or enantioselective osmium-catalyzed dihydroxylation of olefins under near-neutral conditions

K3Fe(CN)6 and NaIO4 serve as catalytic co-oxidants for osmium-catalyzed dihydroxylations that are performed under near-neutral conditions with K2S2O8 as the stoichiometric oxidant and Na2HPO4 as the base. By using either quinuclidine or hydroquinidine 1,4-phthalazinediyl ether [(DHQD)2Phal], good yields of racemic or enantioenriched diols are obtained. This simple, biphasic procedure offers advantages over other neutral dihydroxylation protocols that use N-methylmorpholine oxide as the stoichiometric oxidant, by suppressing the secondary catalytic cycle that leads to reduced enantioselectivities. The utility of the procedure, which is nicely suited for base-labile starting materials or products, is demonstrated by performing the dihydroxylation in the presence of an aliphatic aldehyde moiety.

Cystobactamids 920-1 and 920-2: Assignment of the Constitution and Relative Configuration by Total Synthesis

Total synthesis of cystobactamid 920-1 and its epimer has allowed an unambiguous assignment of the relative and absolute configuration of the natural product. A careful structural analysis of each isomer using both NMR and computational techniques also pr

Enantioselective Dihydroxylation of Alkenes Catalyzed by 1,4-Bis(9-O-dihydroquinidinyl)phthalazine-Modified Binaphthyl–Osmium Nanoparticles

A series of unprecedented binaphthyl–osmium nanoparticles (OsNPs) with chiral modifiers were applied in the heterogeneous asymmetric dihydroxylation of alkenes. A remarkable size effect of the OsNPs, depending on the density of the covalent organic shells, on the reactivity and enantioselectivity of the dihydroxylation reaction was revealed. Successful recycling of the OsNPs was also demonstrated and high reaction efficiency and enantioselectivity were maintained.