122743-18-4

Basic information

• Product Name: METHYL (2R,3S)-(+)-2,3-DIHYDROXY-3-PHENYLPROPIONATE
• Synonyms: METHYL (2R,3S)-(+)-2,3-DIHYDROXY-3-PHENYLPROPIONATE;METHYL (2R,3S)-2,3-DIHYDROXY-3-PHENYLPROPIONATE;methyl (2R,3S)-(+)-2,3-dihydroxy-3-phenyl-propion
• CAS NO: 122743-18-4
• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.2
• Product Categories: Chiral Building Blocks;Esters;Organic Building Blocks
• Mol File: 122743-18-4.mol
• Article Data: 59

Chemical Properties

• Melting Point: 84-88 °C(lit.)
• Boiling Point: 345.2°Cat760mmHg
• Flash Point: 136.6°C
• Appearance: /
• Density: 1.266g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.557
• CAS DataBase Reference: METHYL (2R,3S)-(+)-2,3-DIHYDROXY-3-PHENYLPROPIONATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL (2R,3S)-(+)-2,3-DIHYDROXY-3-PHENYLPROPIONATE(122743-18-4)
• EPA Substance Registry System: METHYL (2R,3S)-(+)-2,3-DIHYDROXY-3-PHENYLPROPIONATE(122743-18-4)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 122743-18-4(Hazardous Substances Data)

Usage

Description

METHYL (2R,3S)-(+)-2,3-DIHYDROXY-3-PHENYLPROPIONATE is an organic compound that serves as a crucial intermediate in the synthesis of various biologically significant molecules and pharmaceuticals. Its unique structure and properties make it a valuable component in the development of new drugs and compounds with potential therapeutic applications.

Uses

Used in Pharmaceutical Synthesis:
METHYL (2R,3S)-(+)-2,3-DIHYDROXY-3-PHENYLPROPIONATE is used as a key intermediate for the synthesis of biologically important 5-phenyl substituted Δ2-thiazolines. These compounds have potential applications in the development of new drugs with various therapeutic properties.
Used in Antidepressant Development:
In the pharmaceutical industry, METHYL (2R,3S)-(+)-2,3-DIHYDROXY-3-PHENYLPROPIONATE is used as an intermediate for the synthesis of (+)-(S)-dapoxetine, an antidepressant medication. METHYL (2R,3S)-(+)-2,3-DIHYDROXY-3-PHENYLPROPIONATE plays a vital role in the development of treatments for depression and related mental health disorders.
Used in Chiral Building Block Synthesis:
METHYL (2R,3S)-(+)-2,3-DIHYDROXY-3-PHENYLPROPIONATE is used as a chiral building block for the preparation of (R)-Cyclohexyl lactic acid. This acid is an essential component in the synthesis of an E-selectin inhibitor, which has potential applications in the treatment of various inflammatory and vascular diseases.
Used in Chemical Research:
In the field of chemical research, METHYL (2R,3S)-(+)-2,3-DIHYDROXY-3-PHENYLPROPIONATE serves as a valuable compound for studying the properties and reactivity of chiral molecules. Its unique structure allows researchers to explore new reaction pathways and develop innovative synthetic strategies for the creation of novel compounds 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+/m0/s1

Upstream product

• 186581-53-3 diazomethane 
• 220820-69-9 (2S,4R,5S)-4-O-t-butyldimethylsilyl-1,2-O-isopropylidene-1,2,4,5-tetrahydroxy-5-phenylpentan-3-one 
• 591-50-4 iodobenzene 
• 292638-85-8 acrylic acid methyl ester 
• 1021491-60-0 (2R,3S)-3-hydroxy-2-(1-methyl-1-phenylethoxy)-3-phenylpropanoic acid methyl ester 
• 1021491-55-3 [[(Z)-1-methoxy-2-(1-methyl-1-phenylethoxy)ethenyl]oxy](trimethyl)silane 
• 100-52-7 benzaldehyde 
• 103-26-4 Methyl cinnamate 
• 103-26-4 methyl cinnamate 
• 100-42-5 styrene 
• 67-56-1 methanol 
• 94594-91-9 acrylcamphorsultam 
• 1020737-67-0 (3aS,4R,7S,7aR)-3-acryloyl-4,8,8-trimethylhexahydro-3H-4,7-methano-1,2,3-benzoxathiazole 2,2-dioxide 
• 196703-87-4 (2R,3S)-2,3-dihydroxy-3-phenylpropionic acid benzyl ester 

Downstream Products

• 186758-09-8 (4R,5S)-2-Methoxy-2-methyl-5-phenyl-[1,3]dioxolane-4-carboxylic acid methyl ester 
• 167357-61-1 (2R,3S)-methyl 2-acetoxy-3-bromo-3-phenylpropanoate 
• 1396842-60-6 (2R,3S)-methyl-3-phenyl-1,4-dioxa-8-azaspiro[4.5]decane-2-carboxylate 
• 1396842-69-5 C₂₄H₂₀F₃N₃O₇S 
• 1396842-61-7 (2R,3S)-8-benzyl 2-methyl-3-phenyl-1,4-dioxa-8-azaspiro[4.5]decane-2,8-dicarboxylate 
• 335317-25-4 (2S,4S,5R)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-allyl ester 
• 335317-39-0 (2S,4S,5R)-2-(4-Methoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-allyl ester 5-methyl ester 
• 335317-38-9 (2R,3S)-3-Allyloxycarbonylamino-2-hydroxy-3-phenyl-propionic acid methyl ester 
• 157240-36-3 (2R,3S)-3-phenylisoserine methyl ester 
• 401480-07-7 (3R,4S)-3,4-Bis-methoxymethoxy-4-phenyl-butan-2-one 
• 158341-43-6 methyl 2-acetoxy-3-azido-3-phenylpropanoate 
• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 99458-15-8 Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate 
• 556038-60-9 (1S,2S,3S)-3-(4-benzyloxy-2,6-dibromophenyl)-4-nitro-1-phenylbutane-1,2-diol 

Relevant articles and documents

Process development of the Sharpless catalytic asymmetric dihydroxylation reaction to prepare methyl (2R,3S)-2,3-dihydroxy-3-phenylpropionate

A typical Sharpless catalytic asymmetric dihydroxylation (ADH) process to make methyl (2R,3S)-2,3-dihydroxy-3 phenylpropionate has been successfully developed. The ADH reaction was exothermic and complete in 2-3 h without affecting the optical purity and

Catalytic asymmetric dihydroxylation of olefins with reusable OsO42- on ion-exchangers: The scope and reactivity using various cooxidants

Exchanger-OsO4 catalysts are prepared by an ion-exchange technique using layered double hydroxides and quaternary ammonium salts covalently bound to resin and silica as ion-exchangers. The ion-exchangers with different characteristics and opposite ion selectivities are specially chosen to produce the best heterogeneous catalyst that can operate using the various cooxidants in the asymmetric dihydroxylation reaction. LDH-OsO4 catalysts composed of different compositions are evaluated for the asymmetric dihydroxylation of trans-stilbene. Resin-OsO4 and SiO2-OsO4 designed to overcome the problems associated with LDH-OsO4 indeed show consistent activity and enantioselectivity in asymmetric dihydroxylation of olefins using K3Fe(CN)6 and molecular oxygen as cooxidants. Compared to the Kobayashi heterogeneous systems, resin-OsO4 is a very efficient catalyst for the dihydroxylation of a wide variety of aromatic, aliphatic, acyclic, cyclic, mono-, di-, and trisubstituted olefins to afford chiral vicinal diols with high yields and enantioselectivities irrespective of the cooxidant used. Resin-OsO4 is recovered quantitatively by a simple filtration and reused for a number of cycles with consistent activity. The high binding ability of the heterogeneous osmium catalyst enables the use of an equimolar ratio of ligand to osmium to give excellent enantioselectives in asymmetric dihydroxylation in contrast to the homogeneous osmium system in which excess molar quantities of the expensive chiral ligand to osmium are invariably used. The complexation of the chiral ligand (DHQD)2PHAL, having very large dimension, a prerequisite to obtain higher ee, is possible only with the OsO42- located on the surface of the supports.

Markedly enhanced recyclability of osmium catalyst in asymmetric dihydroxylation reactions by using macroporous resins bearing both residual vinyl groups and quaternary ammonium moieties

Markedly enhanced recyclability of osmium catalyst in asymmetric dihydroxylation has been achieved by using osmylated macroporous resins bearing both residual vinyl groups and quaternary ammonium moiety. The Royal Society of Chemistry 2005.

Polymeric cinchona alkaloids for the heterogeneous catalytic asymmetric dihydroxylation of olefins: The influence of the polymer backbone polarity on the compatibility between polymer support and reaction medium

Heterogeneous catalytic asymmetric dihydroxylation of olefins using homo- and co-polymeric cinchona alkaloids has been reported. The benzoate type homopolymers 2a,b showed high enantioselectivity in the heterogeneous ADH reactions, but their catalytic eff

Silica gel supported bis-cinchona alkaloid: A highly efficient chiral ligand for heterogeneous asymmetric dihydroxylation of olefins

Comparable reactivity and enantioselectivity to those in homogeneous solution have been achieved in heterogeneous catalytic asymmetry dihydroxylation (AD) of elefins using a new silica gel supported cinchona alkaloid containing 1,4-bis(9-O-quinyl)phthalaz

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.

Highly Enantioselective Iron-Catalyzed cis-Dihydroxylation of Alkenes with Hydrogen Peroxide Oxidant via an FeIII-OOH Reactive Intermediate

The development of environmentally benign catalysts for highly enantioselective asymmetric cis-dihydroxylation (AD) of alkenes with broad substrate scope remains a challenge. By employing [FeII(L)(OTf)2] (L=N,N′-dimethyl-N,N′-bis(2-methyl-8-quinolyl)-cyclohexane-1,2-diamine) as a catalyst, cis-diols in up to 99.8 % ee with 85 % isolated yield have been achieved in AD of alkenes with H2O2as an oxidant and alkenes in a limiting amount. This “[FeII(L)(OTf)2]+H2O2” method is applicable to both (E)-alkenes and terminal alkenes (24 examples >80 % ee, up to 1 g scale). Mechanistic studies, including18O-labeling, UV/Vis, EPR, ESI-MS analyses, and DFT calculations lend evidence for the involvement of chiral FeIII-OOH active species in enantioselective formation of the two C?O bonds.