84311-19-3

Basic information

• Product Name: N-BOC-ALPHA-METHYL-L-SERINE
• Synonyms: (S)-2-BOC-AMINO-3-HYDROXY-2-METHYLPROPIONIC ACID;N-BOC-ALPHA-METHYL-L-SERINE;BOC-(S)-2-AMINO-2-METHYL-3-HYDROXYPROPANOIC ACID;BOC-L-ALPHA-METHYLSERINE;BOC-ALPHA-METHYL-L-SER;L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-2-methyl- (9CI);N-BOC-A-METHYL-L-SERINE;N-Boc-2-Methyl-L-serine, 97%
• CAS NO: 84311-19-3
• Molecular Formula: C₉H₁₇NO₅
• Molecular Weight: 219.23
• EINECS: 1592732-453-0
• Product Categories: N-BOC;pharmacetical;unnatural amino acids
• Mol File: 84311-19-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 126°C
• Boiling Point: 387.1oC at 760 mmHg
• Flash Point: 187.9oC
• Appearance: /
• Density: 1.207g/cm3
• Vapor Pressure: 1.36E-07mmHg at 25°C
• Refractive Index: 1.486
• Storage Temp.: Store below +30°C.
• Solubility: Soluble in dimethylformamide.
• CAS DataBase Reference: N-BOC-ALPHA-METHYL-L-SERINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-ALPHA-METHYL-L-SERINE(84311-19-3)
• EPA Substance Registry System: N-BOC-ALPHA-METHYL-L-SERINE(84311-19-3)

Safety Data

• WGK Germany: WGK 2 water endangering
• HazardClass: IRRITANT
• Hazardous Substances Data: 84311-19-3(Hazardous Substances Data)

Usage

Description

N-BOC-ALPHA-METHYL-L-SERINE, also known as N-Boc-2-methyl-L-serine, is a chemical compound that serves as a building block in the synthesis of various organic molecules and pharmaceuticals. It is characterized by the presence of a Boc-protecting group and a methyl group on the alpha carbon of the L-serine molecule, which provides unique reactivity and selectivity in chemical reactions.

Uses

Used in Organic Synthesis:
N-BOC-ALPHA-METHYL-L-SERINE is used as a building block for the synthesis of complex organic molecules and pharmaceuticals. Its unique structure allows for selective reactions and the formation of specific molecular architectures that are otherwise difficult to achieve.
Used in Diels-Alder Reactions:
N-BOC-ALPHA-METHYL-L-SERINE is used as a cocatalyst in the Diels-Alder reactions between cyclopentadiene and methyl acrylate in the presence of Lewis acids. Its presence enhances the reaction rate and selectivity, leading to the formation of desired products with improved yields.

InChI:InChI=1/C9H17NO5/c1-8(2,3)15-7(14)10-9(4,5-11)6(12)13/h11H,5H2,1-4H3,(H,10,14)(H,12,13)/t9-/m0/s1

Upstream product

• 3398-40-1 (S)-(+)-2-amino-2-methyl-3-hydroxypropanoic acid 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 876913-90-5 tert-butyl (S)-2-(4-hydroxyphenylcarbamoyl)-1-hydroxypropan-2-ylcarbamate 
• 188476-33-7 (S)-2-N-(tert-butoxycarbonyl)amino-2-methyl-3-hydroxypropanoic acid methyl ester 
• 1114394-24-9 C₂₃H₃₇FN₂O₅ 
• 1114394-21-6 C₂₃H₃₇FN₂O₅ 
• 876913-65-4 tert-butyl (S)-2-(4-(octyloxy)phenylcarbamoyl)-1-hydroxypropan-2-ylcarbamate 
• 876914-76-0 tert-butyl (S)-2-(4-(4-phenylphenethyloxy)-3-(trifluoromethyl)phenylcarbamoyl)-1-hydroxypropan-2-ylcarbamate 
• 876914-72-6 {1-[4-(2-biphenyl-4-yl-ethoxy)-3-methyl-phenylcarbamoyl]-2-hydroxy-1-methyl-ethyl}-carbamic acid tert-butyl ester 
• 876914-78-2 tert-butyl (S)-2-(4-(4-phenylphenethyloxy)-3-bromophenylcarbamoyl)-1-hydroxypropan-2-ylcarbamate 

Relevant articles and documents

Progress towards the synthesis of piperazimycin A: synthesis of the non-proteogenic amino acids and elaboration into dipeptides

This Letter describes the synthesis of the five non-proteogenic amino acids required for the total synthesis of piperazimycin A, and synthetic elaboration into multiple dipeptides. Importantly, this Letter details the first example of an elusive piperazic acid-piperazic acid coupling to form this key C5-C14 dipeptide.

Non-natural amino acids as modulating agents of the conformational space of model glycopeptides

The synthesis and conformational analysis in aqueous solution of different α-methyl-α-amino acid di-amides, derived from serine, threonine, β-hydroxycyclobutane-α-amino acids, and their corresponding model β-O-glucopeptides, are reported. The study reveals that the presence of an α-methyl group forces the model peptides to adopt helix-like conformations. These folded conformations are especially significant for cyclobutane derivatives. Interestingly, this feature was also observed in the corresponding model glucopeptides, thus indicating that the α-methyl group and not the β-O-glucosylation process largely determines the conformational preference of the backbone in these structures. On the other hand, atypical conformations of the glycosidic linkage were experimentally determined. Therefore, when a methyl group was located at the Cβ atom with an R configuration, the glycosidic linkage was rather rigid. Never-theless, when the S configuration was displayed, a significant degree of flexibility was observed for the glycosidic linkage, thus showing both alternate and eclipsed conformations of the ψb dihedral angle. In addition, some derivatives exhibited an unusual value for the Φ2 angle, which was far from a value of -60° expected for a conventional β-O-glycosidic linkage. In this sense, the different conformations exhibited by these molecules could be a useful tool in obtaining systems with conformational preferences "a la carte".

Synthesis of (S)-N-tert-butoxycarbonyl-N,O-isopropylidene-α- methylserinal: A potential building block for the asymmetric synthesis of non-natural amino acids

The title compound (S)-α-methylserinal acetonide has been efficiently prepared from (S)-α-methylserine, which is readily available in enantiomerically pure form by Curtius rearrangement of α,α-dialkyl 2- cyanoesters obtained by diastereoselective alkylation of (1S,2R,4R)-10- dicyclohexylsulfamoylisobornyl 2-cyanopropanoate using methoxymethyl iodide or paraformaldehyde as electrophiles by an extension of our recently developed methodology for the synthesis of α,α-dialkylamino acids.