16820-18-1

Basic information

• Product Name: 2-Methyl-L-serine
• Synonyms: (+)-2-Methyl-L-serine;ALPHA-METHYL-D-SER;(R)-3-HYDROXY-2-METHYLALANINE;L-Serine, 2-methyl- (9CI);-Methyl-D-Ser;A-METHYL-D-SER ;(s)-(+)-2-amino-3-hydroxy-2-methylpropionic acid;L-α-methylserine
• CAS NO: 16820-18-1
• Molecular Formula: C4H9NO3
• Molecular Weight: 119.12
• EINECS: 226-565-5
• Product Categories: GLYCINESCAFFOLD;Amino Acid Derivatives;Serine [Ser, S];Aliphatics;Amino Acids & Derivatives;unnatural amino acids
• Mol File: 16820-18-1.mol

Chemical Properties

• Melting Point: 286-288 °C
• Boiling Point: 222.38°C (rough estimate)
• Flash Point: 162.9oC
• Appearance: White/Powder
• Density: 1.3126 (rough estimate)
• Vapor Pressure: 3.77E-06mmHg at 25°C
• Refractive Index: 1.4183 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: DMSO (Slightly, Heated), Water (Slightly)
• PKA: 2.20±0.10(Predicted)
• CAS DataBase Reference: 2-Methyl-L-serine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-L-serine(16820-18-1)
• EPA Substance Registry System: 2-Methyl-L-serine(16820-18-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-37/39-26
• Hazardous Substances Data: 16820-18-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Methyl-L-serine is used as a chiral building block for the synthesis of different α-methyl α-amino acids, which are essential components in the development of various pharmaceutical compounds. Its unique structure allows for the creation of novel drugs with improved efficacy and selectivity.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-Methyl-L-serine is utilized as a key component in the production of various α-methyl α-amino acids. These amino acids are crucial for the development of new molecules with specific properties and applications, such as in the creation of novel drugs, agrochemicals, and other specialty chemicals.
Used in Research and Development:
2-Methyl-L-serine is also employed in research and development settings, where it is used to study the properties and behavior of chiral compounds. Its unique structure makes it an ideal candidate for exploring the effects of chirality on molecular interactions and reactivity, leading to a deeper understanding of stereochemistry and its implications in various fields.

InChI:InChI=1/C4H9NO3/c1-4(5,2-6)3(7)8/h6H,2,5H2,1H3,(H,7,8)/t4-/m0/s1

Upstream product

• 50-00-0 formaldehyd 
• 56-41-7 L-alanin 
• 96293-17-3 (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide 
• 121704-29-8 3-Hydroxy-2-(2-methoxy-acetylamino)-2-methyl-propionic acid 
• 657401-76-8 methyl hydrogen 2-(<(tert-butyl)dimethylsilyl>oxymethyl)-2-methylmalonate 
• 1059607-23-6 (1S,4S,7S,8R)-4,8,11,11-tetramethyl-4-(hydroxymethyl)-6-oxa-3-aza-tricyclo[6.2.1.0^2,7]undec-2-en-5-one 
• 1059607-17-8 (1R,4S,7R,8S)-1,4,11,11-tetramethyl-4-(hydroxymethyl)-6-oxa-3-aza-tricyclo[6.2.1.0^2,7]undec-2-en-5-one 
• 1059607-24-7 (1S,4R,7S,8R)-4,8,11,11-tetramethyl-4-(hydroxymethyl)-6-oxa-3-aza-tricyclo[6.2.1.0^2,7]undec-2-en-5-one 
• 1059607-25-8 (1R,4R,7R,8S)-1,4,11,11-tetramethyl-4-(hydroxymethyl)-6-oxa-3-aza-tricyclo[6.2.1.0^2,7]undec-2-en-5-one 
• 1217606-86-4 (R)-2-azido-3-hydroxy-2-methyl-propionic acid 
• 298704-91-3 (3S,6R)-N-1-(tert-butoxycarbonyl)-3-hydroxymethyl-6-isopropyl-3-methyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone 
• 72953-33-4 (3R,6S)-Hydroxymethyl-2,5-dimethoxy-3,6-dimethyl-3,6-dihydropyrazin 
• 338-69-2 D-Alanine 
• 114396-62-2 (S)-α-methylserine hydrochloride 

Downstream Products

• 84311-19-3 (S)-2-tert-Butoxycarbonylamino-3-hydroxy-2-methyl-propionic acid 
• 188476-33-7 (S)-2-N-(tert-butoxycarbonyl)amino-2-methyl-3-hydroxypropanoic acid methyl ester 
• 147316-32-3 (2S)-methyl 2-amino-3-hydroxy-2-methylpropanoate 
• 50-00-0 formaldehyd 
• 56-41-7 L-alanin 
• 114396-70-2 (S)-N-Cbz-α-MeSer(OH)-OH 
• 84311-18-2 (R)-2-N-(tert-butoxycarbonyl)amino-2-methyl-3-hydroxy-propanoic acid 
• 72953-37-8 methyl (R)-(+)-2-amino-3-hydroxy-2-methylpropionate 
• 114396-63-3 (S)-methyl 2-amino-3-hydroxy-2-methylpropanoate hydrochloride 
• 207117-28-0 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methyl-propionic acid 

Relevant articles and documents

Method for preparing 2-methylserine

The invention relates to a method for preparing 2-methylserine, and mainly solves the technical problem of being long in route, complicated in operation, and not conducive to mass production of the existing synthetic method. The method comprises the following steps: Cbz-chiral alanine and Benzaldehyde dimethyl acetal are reacted under the action of thionyl chloride and zinc chloride, a reaction product is crystallized to obtain an intermediate 1, the intermediate 1 is reacted under cooperation of an alkaline reagent to obtain an intermediate 2, an intermediate 3 is obtained from the intermediate 2 by the action of lithium hydroxide, and the final product 2-methylserine is obtained from the intermediate 3 by palladium carbon catalytic hydrogenolysis. High purity 2-methylserine can be obtained by the method.

A concise synthesis of (+)-conagenin and its isomer using chiral tricyclic iminolactones

An efficient synthesis of (+)-conagenin, a novel immunomodulator produced by Streptomyces roseosporus, has been achieved via the shortest route at present. At the same time, 2-epiconagenin was synthesized according to the same methodology.

Cloning of the gene encoding α-methylserine hydroxymethyltransferase from Aminobacter sp. AJ110403 and Ensifer sp. AJ110404 and characterization of the recombinant enzyme

Genes encoding α-methylserine hydroxymethyltransferase from Aminobacter sp. AJ110403 and Ensifer sp. AJ110404 were cloned and expressed in Escherichia coli. The purified enzymes were homodimers with a 46-kDa subunit and contained 1 mol/mol-subunit of pyridoxal 5′-phosphate. The V max of these enzymes catalyzing the conversion of α-methyl-L-serine to D-alanine via tetrahydrofolate was 22.1 U/mg (AJ110403) and 15.4 U/mg (AJ110404).

Theoretical evidence for pyramidalized bicyclic serine enolates in highly diastereoselective alkylations

A new chiral serine equivalent and its enantiomer have been synthesized from (S)- and (R)-N-Bocserine methyl esters (Boc: tert-butyloxy-carbonyl). The use of these compounds as chiral building blocks has been demonstrated in the synthesis of α-alkyl α-amino acids by diastereoselective po tassium enolate alkylation reactions and subsequent acid hydrolyses. Theoretical studies were performed to eluci date the stereochemical outcome of both the formation of five-membered cyclic N,O-acetals and the subsequent alkylation process, which occurs with total retention of configuration. This feature could be explained in terms of the high degree of pyramidalization of enolate intermediates.

Stereoselective addition of organometallic reagents to a chiral acyclic nitrone derived from L-erythrulose

The additions of various organolithium and organomagnesium reagents to a chiral nitrone prepared from L-erythrulose took place with variable diastereoselectivity. The degree and strength of the facial selectivity can be modified if the reaction is performed in the presence of Lewis acid additives: zinc bromide enhances the attack to the Si face of the C=N bond whereas diethyl aluminium chloride promotes attack to the Re face. The obtained adducts can be then transformed into protected N-hydroxy-α,α-disubstituted-α- amino acid derivatives as well as into the corresponding α,α- disubstituted α-amino acids.

Enantioselective synthesis of α-methyl-D-cysteine and lanthionine building blocks via α-methyl-d-serine-β-lactone

(Matrix presented) We report here the enantioselective synthesis of Boc-α-methyl-D-cysteine(PMB)-OH and lanthionine building blocks through the regioselective ring opening of key intermediate Boc-α -methyl-D-serine-β-lactone.

Synthesis of α,α-disubstituted α-amino acid derivatives in enantiopure form via stereoselective addition of Grignard reagents to a chiral acyclic nitrone derived from L-erythrulose

The additions of various Grignard reagents to a chiral nitrone prepared from L-erythrulose take place with variable diastereoselectivity. The degree and strength of the facial selectivity can be modified if the reaction is performed in the presence of Lewis acidic additives: zinc bromide enhances attack to the si face whereas diethyl aluminum chloride promotes attack to the re side. The obtained adducts can be then efficiently transformed into protected N-hydroxy α,α-disubstituted α-amino acid derivatives as well as into the corresponding α,α-disubstituted α-amino acids.

Asymmetric synthesis of (S)-and (R)-α-methylserine based on the chiral recyclable reagent (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide

Both enantiomers of α-methylserine were synthesized with the use of NiII complexes based on the chiral recyclable reagent (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide. Intermediate diastereomeric complexes were separated by crystal

Novel and efficient transformation of α-amino nitrile to α-imino and α-amide nitriles in asymmetric Strecker synthesis

Oxidation of α-amino nitrile 4 with ozone gave rise to a mixture of α-imino nitrile 5 and a novel fragmentation product of 6 in one-step. The mixture was converted to a variety of α-substituted α-amino acids 7 in high yields, which enabled the asymmetric transferring Strecker synthesis to be a widely useful method.

Enantioselective synthesis of (S)- and (R)-α-methylserines: Application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals

This report describes the synthesis of enantiomerically pure (S)- and (R)-α-methylserines on a multigram scale, starting from the Weinreb amide of 2-methyl-2-propenoic acid and using a stereodivergent synthetic route that involves a Sharpless asymmetric dihydroxylation reaction. As a synthetic application of these quaternary α-amino acids, they were used as starting materials in the synthesis of the well-known valuable homochiral (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinal building blocks.