(R)-(-)-Methyl mandelate

Base Information

• Chemical Name: (R)-(-)-Methyl mandelate
• CAS No.: 20698-91-3
• Molecular Formula: C9H10O3
• Molecular Weight: 166.177
• Hs Code.: 29181990
• European Community (EC) Number: 869-825-9
• DSSTox Substance ID: DTXSID10369195
• Nikkaji Number: J74.109D
• Wikidata: Q72492485
• Mol file: 20698-91-3.mol

Synonyms:20698-91-3;(R)-(-)-Methyl mandelate;Methyl (R)-(-)-mandelate;(R)-Methyl 2-hydroxy-2-phenylacetate;methyl (2R)-2-hydroxy-2-phenylacetate;D-(-)-Mandelic Acid Methyl Ester;(r)-methyl mandelate;Methyl D-(-)-Mandelate;(R)-mandelic acid methyl ester;(R)-(-)-Mandelic acid methyl ester;Methyl hydroxy(phenyl)acetate #;Methyl(R)-(-)-Mandelate;(-)-D-Mandelic acid methyl ester;MFCD00064247;methyl (R)-2-hydroxy-2-phenylacetate;methyl (r)-mandelate;D-Mandelic acid methyl;(-)-Methyl (R)-alpha-hydroxyphenylacetate;(R)-O-methylmandelic acid;Methyl (R)-(?)-mandelate;SCHEMBL186900;BDBM36087;DTXSID10369195;R(-)-Mandelic acid methyl ester;FD1307;AKOS005146057;AKOS015855478;CS-W017868;Methyl (R)-(-)-mandelate, >=99%;AS-14338;methyl (R)-(-)-2-hydroxy-2-phenylacetate;M1349;EN300-1174643;A814822;(R)-(-)-alpha-Hydroxyphenylacetic acid methyl ester;J-013532;Benzeneacetic acid, .alpha.-hydroxy-, methyl ester, (R)-;methyl 2-hydroxy-2-phenyl-acetate;Methyl (R)-(-)-Mandelate;Benzeneacetic acid, .alpha.-hydroxy-, methyl ester, (.alpha.R)-

Chemical Property of (R)-(-)-Methyl mandelate

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0.00715mmHg at 25°C
• Melting Point: 56-58 °C
• Refractive Index: 1.535
• Boiling Point: 258.1 °C at 760 mmHg
• PKA: 12.19±0.20(Predicted)
• Flash Point: 113.1 °C
• PSA: 46.53000
• Density: 1.182 g/cm³
• LogP: 0.89300
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Sparingly, Sonicated)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 166.062994177
• Heavy Atom Count: 12
• Complexity: 150

Purity/Quality:

99% ^*data from raw suppliers

Methyl (R)-(?)-mandelate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(C1=CC=CC=C1)O
• Isomeric SMILES: COC(=O)[C@@H](C1=CC=CC=C1)O
• Uses: Methyl (R)-(-)-Mandelate is used in the synthesis of (-)-Maoecrystal V, an ent-kauranoid analogue with selective and potent cytotoxic activity.

Technology Process of (R)-(-)-Methyl mandelate

There total 116 articles about (R)-(-)-Methyl mandelate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methanol (67-56-1) + (R)-Mandelic Acid (611-71-2) → (R)-methyl mandelate (20698-91-3)

Guidance literature:

With toluene-4-sulfonic acid; for 3h; Heating;

DOI:10.1055/s-2005-868518

Reference yield: 100.0%

1-methyl-1-nitrosourea (684-93-5) + (R)-Mandelic Acid (611-71-2) → (R)-methyl mandelate (20698-91-3)

Guidance literature:

With potassium hydroxide; In diethyl ether; water; at 0 ℃; for 0.25h;

DOI:10.1039/c4ob00601a

Reference yield: 98.0%

methyl 2-oxo-2-phenylacetate (15206-55-0) → (S)-Methyl mandelate (21210-43-5) + (R)-methyl mandelate (20698-91-3)

Guidance literature:

With formic acid*triethylamine; Ru/(S,S)-DPEN/MCF; In isopropyl alcohol; at 20 ℃; for 12h;

DOI:10.1039/b615564b

upstream raw materials:

methanol

MANDELIC ACID

diazomethane

(R)-Mandelic Acid

Downstream raw materials:

(R)-1,1,2-triphenylethane-1,2-diol

(E)-But-2-enedioic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (R)-methoxycarbonyl-phenyl-methyl ester

(R)-methyl 2-propionyloxy-2-phenylethanoate

(R)-methyl 2-tert-butoxy-2-phenylacetate

Refernces

• 1、 Weber, Edwin,Hager, Orm,Foces-Foces, Concepcion,Llamas-Saiz, Antonio L.. "Supramolecular crystalline construction based on a mandelic acid source. host design, inclusion formation and X-ray crystal structures of a methanol inclusion complex and free host structures in racemic and optically resolved forms". . p. 50 - 60. Retrieved 1996.
• 2、 Zehani, Sadek,Lin, Jian,Gelbard, Georges. "REDUCTIONS WITH NADH MODELS II: ASYMMETRIC INDUCTION WITH SUGAR SUBSTITUTED HANTZSCH ESTERS OR WITH CHIRAL LEWIS ACIDS". . p. 733 - 740. Retrieved 1989.
• 3、 Li, Xianfeng,Tanner, Dennis D.. "A new type of NADH model compound: Synthesis and reactions". . p. 3275 - 3278. Retrieved 1996.
• 4、 Steiner, Ivo,Aufdenblatten, Rhony,Togni, Antonio,Blaser, Hans-Ulrich,Pugin, Benoit. "Novel silica gel supported chiral biaryl-diphosphine ligands for enantioselective hydrogenation". . p. 2307 - 2311. Retrieved 2004.
• 5、 Mikata, Yuji,Mizukami, Kiyoko,Ikehara, Kenji,Ohno, Atsuyoshi. "The Enzyme/Coenzyme/Metal/Substrate Quaternary Complex Generated in the Transition State of the Reduction of Benzoylformate with NAD(P)H Models". . p. 6491 - 6494. Retrieved 1995.
• 6、 Talas, Emilia,Margitfalvi, Jozsef L.,Egyed, Orsolya. "Additional data to the origin of rate enhancement in the enantioselective hydrogenation of activated ketones over cinchonidine modified platinum catalyst". . p. 191 - 198. Retrieved 2009.
• 7、 Kanomata,Nakata. "Highly enantioselective reduction with novel, bridged NADH models". . p. 1207 - 1211. Retrieved 1997.
• 8、 Huerta, Fernando F.,Laxmi, Y.R. Santosh,Baeckvall, Jan-E.. "Dynamic kinetic resolution of α-hydroxy acid Esters". . p. 1037 - 1040. Retrieved 2000.
• 9、 Bekele, Tefsit,Shah, Meha H.,Wolfer, Jamison,Abraham, Ciby J.,Weatherwax, Anthony,Lectka, Thomas. "Catalytic, enantioselective [4 + 2]-cycloadditions of ketene enolates and o-quinones: Efficient entry to chiral, α-oxygenated carboxylic acid derivatives". . p. 1810 - 1811. Retrieved 2006.
• 10、 Sano, Shogo,Beier, Matthias Josef,Mallat, Tamas,Baiker, Alfons. "Potential of ionic liquids as co-modifiers in asymmetric hydrogenation on platinum". . p. 117 - 124. Retrieved 2012.