23680-31-1

Basic information

• Product Name: N-BOC-O-Benzyl-L-serine
• Synonyms: N-BOC-O-Benzyl-L-ser;N-Boc-O-benzyl-L-serine Boc-Ser(Bzl)-OH;Boc-Ser(Bz1)-OH;(S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)aMino)propanoic acid;(2S)-3-Benzyloxy-2-(tert-butoxycarbonylamino)propanoic acid;Boc-Ser(Bzl)-OH >=99.0% (T);L-SERINE-N-T-BOC, O-BZ ETHER (15N);L-SERINE-N-T-BOC, O-BZ ETHER (2-13C)
• CAS NO: 23680-31-1
• Molecular Formula: C₁₅H₂₁NO₅
• Molecular Weight: 295.33
• EINECS: 245-820-1
• Product Categories: Amino Acids;Boc-Amino Acids and Derivative;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Boc-Amino acid series
• Mol File: 23680-31-1.mol
• Article Data: 36

Chemical Properties

• Melting Point: 58-60 °C(lit.)
• Boiling Point: 437.02°C (rough estimate)
• Flash Point: 229.7 °C
• Appearance: /Solid
• Density: 1.1454 (rough estimate)
• Vapor Pressure: 4.07E-09mmHg at 25°C
• Refractive Index: 22 ° (C=2, EtOH)
• Storage Temp.: 2-8°C
• PKA: 3.53±0.10(Predicted)
• BRN: 3064461
• CAS DataBase Reference: N-BOC-O-Benzyl-L-serine(CAS DataBase Reference)
• NIST Chemistry Reference: N-BOC-O-Benzyl-L-serine(23680-31-1)
• EPA Substance Registry System: N-BOC-O-Benzyl-L-serine(23680-31-1)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 23680-31-1(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

N-Boc-O-benzyl-L-serine, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

InChI:InChI=1/C15H21NO5/c1-15(2,3)21-14(19)16-12(13(17)18)10-20-9-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,16,19)(H,17,18)/p-1/t12-/m0/s1

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 5445-44-3 O-benzylserine 
• 4726-96-9 O-Benzyl-L-serine 
• 98015-52-2 1,2,2,2-Tetrachloroethyl tert-Butyl Carbonate 
• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 
• 100-39-0 benzyl bromide 
• 620-05-3 iodomethylbenzene 
• 69871-79-0 (S)-benzyl 3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 3850-40-6 N-Boc-DL-serine 
• 2712-78-9 bis-[(trifluoroacetoxy)iodo]benzene 
• 30200-52-3 Boc-Ser(Bzl)-OH*CHA 

Downstream Products

• 72287-78-6 (S)-2-((S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionylamino)-succinamic acid 4-nitro-benzyl ester 
• 99732-84-0 Boc-Ala-Gln-Ser(Bzl)-Gly-OCH₃ 
• 47924-54-9 L-Glutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosylglycyl-L-leucyl-L-arginyl-L-prolylglycinamide 
• 76398-77-1 N-(t-butoxycarbonyl)-O-benzyl-L-serine N-hydroxy-5-norbornene-2,3-dicarboximide ester 
• 79722-11-5 Benzyl-N-(tert-butyloxycarbonyl)-O-benzyl-(S)-serinehydroxamate 
• 77124-58-4 pGlu-His-Trp-Ser 
• 90013-41-5 O-benzyl-N-(t-butoxycarbonyl)serine methylamide 
• 81531-47-7 N--Phe-Pro-Lactam 
• 158573-53-6 (S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionic acid 2-(2-hydroxy-ethoxy)-ethyl ester 
• 139338-69-5 (S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionic acid 2-[2-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-ethoxy]-ethyl ester 
• 298713-03-8 N-Boc-O-benzyl-D,L-serine tetradecylamide 
• 173439-88-8 ((S)-2-Benzyloxy-1-hexadecylcarbamoyl-ethyl)-carbamic acid tert-butyl ester 
• 42382-93-4 (S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionic acid pentachlorophenyl ester 
• 197707-00-9 (S)-3-Benzyloxy-2-tert-butoxycarbonylamino-propionic acid 2-(2-{2-[2-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propionyloxy)-ethoxy]-ethoxy}-ethoxy)-ethyl ester 

Relevant articles and documents

Aryloxy Triester Phosphoramidates as Phosphoserine Prodrugs: A Proof of Concept Study

The specific targeting of protein-protein interactions by phosphoserine-containing small molecules has been scarce due to the dephosphorylation of phosphoserine and its charged nature at physiological pH, which hinder its uptake into cells. To address these issues, we herein report the synthesis of phosphoserine aryloxy triester phosphoramidates as phosphoserine prodrugs that are enzymatically metabolized to release phosphoserine. This phosphoserine-masking approach was applied to a phosphoserine-containing inhibitor of 14-3-3 dimerization, and the generated prodrugs exhibited improved pharmacological activity. Collectively, this provided a proof of concept that the masking of phosphoserine with biocleavable aryloxy triester phosphoramidate masking groups is a viable intracellular delivery system for phosphoserine-containing molecules. Ultimately, this will facilitate the discovery of phosphoserine-containing small-molecule therapeutics.

SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds having potency in the modulation of NMDA receptor activity. Such compounds can be used in the treatment of conditions such as depression and related disorders as well as other disorders.

Development of a Unique Heterogeneous Palladium Catalyst for the Suzuki–Miyaura Reaction using (Hetero)aryl Chlorides and Chemoselective Hydrogenation

A unique heterogeneous palladium catalyst (7% Pd/WA30) supported on an anion exchange resin, which contains N,N-dimethylaminoalkyl functionalities on the polymer backbone, was developed. 7% Pd/WA30 could smoothly catalyze Suzuki–Miyaura reactions of even less reactive heteroaryl chlorides and heteroarylboronic acids to afford various (hetero)biaryls due to the electron-donating effect of the tert-amines on WA30 to Pd species. It was also applicable as a chemoselective hydrogenation catalyst, showing inactivity for the hydrogenolysis of tert-butyldimethylsilyl (TBS) ethers, alkyl benzyl ethers, and benzyl alcohols. The tert-amines on WA30 acted as moderate catalyst poisons for Pd, resulting in chemoselective hydrogenation. 7% Pd/WA30 was reused for at least five times without any loss of the hydrogenation catalytic activity. (Figure presented.).