114396-62-2

Basic information

• Product Name: 1.6. 2-METHYL-L-SERINE HYDROCHLORIDE
• Synonyms: 1.6. 2-METHYL-L-SERINE HYDROCHLORIDE
• CAS NO: 114396-62-2
• Molecular Formula: C₄H₉NO₃*ClH
• Molecular Weight: 155.58
• Mol File: 114396-62-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1.6. 2-METHYL-L-SERINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1.6. 2-METHYL-L-SERINE HYDROCHLORIDE(114396-62-2)
• EPA Substance Registry System: 1.6. 2-METHYL-L-SERINE HYDROCHLORIDE(114396-62-2)

Safety Data

• Hazardous Substances Data: 114396-62-2(Hazardous Substances Data)

Usage

General Description

1,6. 2-Methyl-L-serine hydrochloride is a chemical compound that is a derivative of the amino acid serine. It is a crystalline, water-soluble substance that is used in the synthesis of pharmaceuticals and research chemicals. 1.6. 2-METHYL-L-SERINE HYDROCHLORIDE is known for its role in the production of various drugs and is also used as a chiral building block for the development of new molecules. Its application in the pharmaceutical industry makes it an important compound for drug discovery and development.

Upstream product

• 147316-32-3 (2S)-methyl 2-amino-3-hydroxy-2-methylpropanoate 
• 945544-16-1 (3S,7R,7aS)-tetrahydro-7-methoxy-3,7,7a-trimethyl-5-oxo-2H-oxazolo-[3,2-c]oxazole-3-carboxylic acid methyl ester 
• 185525-79-5 (2R,4S)-2-tert-butyl-3-formyl-4-methyl-1,3-oxazolidine-4-carboxylic acid 

Downstream Products

• 114396-70-2 (S)-N-Cbz-α-MeSer(OH)-OH 
• 207117-28-0 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-2-methyl-propionic acid 
• 3398-40-1 (S)-(+)-2-amino-2-methyl-3-hydroxypropanoic acid 

Relevant articles and documents

Enantioselective Synthesis of α-Substituted Serine Derivatives via Cu-Catalyzed Oxidative Desymmetrization of 2-Amino-1,3-diols

The enantioselective copper-catalyzed oxidative desymmetrization for the synthesis of chiral α-substituted serine derivatives is reported. The combination of Cu(OTf)2/(R,R)-PhBOX catalyst system, N-bromosuccinimide, and MeOH enables us to provide chiral α-substituted serines from N-2-methylbenzoyl-protected 2-amino-1,3-diols through a simple procedure at room temperature under an air atmosphere. A variety of α-substituent including aryl and heteroaryl groups were tolerated in this method, and the corresponding chiral serine derivatives were obtained in good to high yields with high enantioselectivities.

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.

METHOD FOR PRODUCING ALPHA-METHYLATED CYSTEINE AND SERINE DERIVATIVES

The invention relates to an improved method for the production, purification and crystallisation of alpha -methylated cysteine or serine derivatives by an acid hydrolysis of corresponding thiazolidine or oxazolidine esters, with the continuous removal of the accumulating aldehyde, a prior optional conversion into a thiazolidine or oxazolidine carboxylic acid or a thiazolidine or oxazolidine carboxylate and a subsequent azeotropic distillation.

Synthesis of a new conformationally constrained glycoamino acid building block

The synthesis of a suitably protected β-D-glucopyranosyl-(S)-α-methylserine derivative - a new conformationally constrained glycosylated quaternary amino acid analogue of β-D-glucopyranosyl-L-serine - is described. This compound can be used as an attractive building block for the synthesis of new, constrained glycopeptides.

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.