60022-62-0

Basic information

• Product Name: L-Serine benzyl ester hydrochloride
• Synonyms: SERINE-OBZL HCL;L-SERINE BENZYL ESTER HYDROCHLORIDE;H-SER-OBZL HCL;L-SerinebenzylesterHCl;benzyl 2-aMino-3-hydroxypropanoate hydrochloride;L-Serine benzyl ester hydrochloride≥ 99% (TLC);L-β-Hydroxyalanine benzyl ester hydrochloride
• CAS NO: 60022-62-0
• Molecular Formula: C₁₀H₁₃NO₃*ClH
• Molecular Weight: 231.68
• Product Categories: Amino Acid Benzyl Esters;Amino Acids;Amino Acids (C-Protected);Biochemistry
• Mol File: 60022-62-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 175°C
• Boiling Point: 388 °C at 760 mmHg
• Flash Point: 188.4 °C
• Appearance: /
• Vapor Pressure: 8E-06mmHg at 25°C
• Refractive Index: -12 ° (C=1, H2O)
• Storage Temp.: −20°C
• Water Solubility: Soluble in water.
• CAS DataBase Reference: L-Serine benzyl ester hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: L-Serine benzyl ester hydrochloride(60022-62-0)
• EPA Substance Registry System: L-Serine benzyl ester hydrochloride(60022-62-0)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 60022-62-0(Hazardous Substances Data)

Usage

Chemical Properties

Colorless solid

Uses

It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

InChI:InChI=1/C10H13NO3.ClH/c11-9(6-12)10(13)14-7-8-4-2-1-3-5-8;/h1-5,9,12H,6-7,11H2;1H/t9-;/m0./s1

Upstream product

• 56-45-1 L-serin 
• 100-51-6 benzyl alcohol 
• 59524-02-6 (R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate 

Downstream Products

• 73724-45-5 N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine 
• 142757-92-4 <1S-(1α,2α,3α,4α)>-2-<<3-<<<1-(hydroxymethyl)-2-oxo-2-(phenylmethoxy)ethyl>amino>carbonyl>-7-oxabicyclo<2.2.1>hept-2-yl>methyl>benzenepropanoic acid methyl ester 
• 150013-56-2 3-{2-[(1S,2R,3S,4R)-3-((S)-1-Benzyloxycarbonyl-2-hydroxy-ethylcarbamoyl)-7-oxa-bicyclo[2.2.1]hept-2-ylmethyl]-phenyl}-2,2-dimethyl-propionic acid methyl ester 
• 246048-04-4 benzyl (S)-2-(5-(dimethylamino)naphthalene-1-sulfonamidyl)-3-hydroxypropionate 
• 359868-56-7 2-benzyloxycarbonylamino-4-(1-benzyloxycarbonyl-2-hydroxyethylcarbamoyl)butyric acid benzyl ester 
• 1186005-95-7 N-lauroyl-L-serine benzyl ester 
• 123765-20-8 benzyl (2S)-2-amino-3-[tert-butyl(dimethyl)silyl]oxypropanoate 
• 188743-65-9 (S)-benzyl 2-(2-(benzyloxy)benzamido)-3-hydroxypropanoate 
• 1227491-12-4 (S)-benzyl 2-(4-fluoro-3-nitrobenzamido)-3-hydroxypropanoate 
• 1227492-08-1 (S)-benzyl 2-(2-chlorobenzamido)-3-hydroxypropanoate 
• 1227491-13-5 (S)-benzyl 2-(4-methoxybenzamido)-3-hydroxypropanoate 
• 1246972-70-2 N-(3-benzyloxycarbonyl-β-carbolin-1-yl)ethyl-L-serine benzyl ester 
• 1226954-66-0 (S)-benzyl 2-biphenyl-4-ylcarboxamido-3-hydroxypropanoate 
• 1738-90-5 N-(Benzyloxycarbonyl)-L-leucyl-L-serin-benzylester 

Relevant articles and documents

N-transfer reagent and method for preparing the same and its application

Provided are a novel N-transfer reagent and a method for preparing the same and its application. The N-transfer reagent is represented by the following Formula (I): The various novel N-transfer reagents of the present invention can be quickly prepared by employing different nitrobenzene precursors. The N-transfer reagents can directly convert a variety of amino compounds into diazo compounds under mild conditions. Particularly, the N-transfer reagents can facilitate the synthesis of the diazo compounds. The application of synthesizing diazo compounds of the present invention can greatly decrease the difficulty in operation, increase the safety during experiments, reduce the cost of production and the environmental pollution, and enhance the industrial value of diazo compounds.

Serine and threonine Schiff base esters react with β-anomeric peracetates in the presence of BF3·Et2O to produce β-glycosides

Improved procedures are reported for the glycosylation of L-serine and L-threonine utilizing activated Schiff base glycosyl acceptors, which are less expensive and more efficient alternatives to published methods. L-serine or L-threonine benzyl ester hydrochloride salts were reacted with the diarylketimine bis-(4-methoxyphenyl)-methanimine in CH3CN at rt to form the more nucleophilic Schiff bases 3a and 3b in excellent yield. These Schiff bases exhibited ring-chain tautomerism in CDCl3 as shown by 1H NMR. Schiff bases 3a and 3b, acting as glycosyl acceptors, reacted at rt with simple sugar peracetate donors with BF3·OEt 2 promotion to provide the corresponding L-serine and L-threonine O-linked glycosides in excellent yields and purities. The dipeptide ester Schiff base Ar2C = N-Ser-Val-OCH3 3e also reacted to provide β-glycosides in excellent yields, and without epimerization. With microwave irradiation the reactions were complete in 2 to 5 min. To investigate this reaction further, classical AgOTf-promoted Koenigs-Knorr reaction of D-glucopyranosyl, lactosyl, and maltosyl bromides were examined, providing the β-glycosides with yields ranging from 35% to 68%. The difference in reactivity between α- and β-carbohydrate peracetate donors was remarkable. The less configurationally stable D-xylopyranosyl tetra-acetate (a pentose) showed no selectivity (αvsβ-configuration) toward the Schiff bases. Copyright Taylor & Francis Group, LLC.

IMPROVED METHOD FOR MAKING AMINO ACID CLYCOSIDES AND GLYCOPEPTIDES

The invention relates to an improved method of preparing amino glycosides and glycopeptides. The method involves reacting an diarylketimine with an amino acid having a hydroxal side chain to produce an imino-bound intermediate compound. This intermediate is then reacted with an acetylated sugar residue under suitable conditions to yield amino glycoside. The synthetic amino glycoside may be incorporated into a peptide chain under conditions compatible with standard glycopeptide synthesis reactions.