21209-51-8

Basic information

• Product Name: Z-SER-OBZL
• Synonyms: Z-L-SERINE BENZYL ESTER;Z-L-SERINE ALPHA-BENZYL ESTER;Z-SERINE-OBZL;Z-SER-OBZL;N-Z-L-SERINE BENZYL ESTER;N-CBZ-L-SERINE BENZYL ESTER;N-CBZ-SERINE BENZYL ESTER;N-CARBOBENZOXY-L-SERINE BENZYL ESTER
• CAS NO: 21209-51-8
• Molecular Formula: C₁₈H₁₉NO₅
• Molecular Weight: 329.35
• Mol File: 21209-51-8.mol

Chemical Properties

• Melting Point: 83-86 °C(lit.)
• Boiling Point: 534.472 °C at 760 mmHg
• Flash Point: 277.039 °C
• Appearance: /
• Density: 1.253
• Vapor Pressure: 2.97E-12mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: Store at RT.
• Solubility: Chloroform, Methanol
• PKA: 10.46±0.46(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: Z-SER-OBZL(CAS DataBase Reference)
• NIST Chemistry Reference: Z-SER-OBZL(21209-51-8)
• EPA Substance Registry System: Z-SER-OBZL(21209-51-8)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 21209-51-8(Hazardous Substances Data)

Usage

Uses

Used in Peptide Synthesis:
Z-SER-OBZL is used as a building block in peptide synthesis for the creation of complex peptide structures. Its role in this process is essential, as it aids in the formation of peptide bonds, which are the foundation of proteins and essential for various biological functions.
Used in Biochemical Research:
As a biochemical reagent, Z-SER-OBZL is employed in various research applications, including the study of enzyme kinetics, protein structure, and function. Its use in these areas contributes to a deeper understanding of biological processes and the development of novel therapeutic strategies.
Used in Pharmaceutical Industry:
Z-SER-OBZL serves as a pharmaceutical intermediate, playing a vital role in the synthesis of various drugs. Its presence in the drug development process allows for the creation of new and improved medications, ultimately benefiting patients and advancing the field of medicine.
Used in Synthesis of N-benzyloxycarbonyl-O-tert-butyl-(lor dl)-serine benzyl ester:
Z-SER-OBZL is also used to synthesize the corresponding N-benzyloxycarbonyl-O-tert-butyl-(lor dl)-serine benzyl ester, which is another important compound in the field of organic chemistry and pharmaceuticals. This synthesis further expands the range of applications for Z-SER-OBZL and highlights its versatility in chemical processes.

InChI:InChI=1/C18H19NO5/c20-11-16(17(21)23-12-14-7-3-1-4-8-14)19-18(22)24-13-15-9-5-2-6-10-15/h1-10,16,20H,11-13H2,(H,19,22)/t16-/m0/s1

Upstream product

• 1145-80-8 N-(benzyloxycarbonyl)-L-serine 
• 104-15-4 toluene-4-sulfonic acid 
• 100-51-6 benzyl alcohol 
• 1738-80-3 L-serine benzyl ester p-toluenesulfonate hydrochoride 
• 501-53-1 benzyl chloroformate 
• 2016-04-8 N,N-dimethylformamide dibenzyl acetal 
• 100-44-7 benzyl chloride 
• 2978-10-1 O-benzyl-N,N'-diisopropylisourea 
• 100-39-0 benzyl bromide 

Downstream Products

• 1186-34-1 L-serine ethanolamine phosphate 
• 2643-42-7 O,O'-hydroxyphosphoryl-di-L-serine 
• 77870-95-2 ester benzylique de la N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-serine 
• 77870-94-1 ester benzylique de la N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-serine 
• 77884-92-5 ester benzylique de la N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-L-serine 
• 77870-97-4 ester benzylique de la N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-serine 
• 110797-32-5 (S)-2-Benzyloxycarbonylamino-3-((2R,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-propionic acid benzyl ester 
• 83956-33-6 O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine benzyl ester 
• 133510-64-2 (S)-3-[(2R,3S,5R)-5-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-(2-methoxy-acetoxy)-tetrahydro-furan-2-ylmethoxymethoxy]-2-benzyloxycarbonylamino-propionic acid benzyl ester 
• 121542-12-9 (S)-2-Benzyloxycarbonylamino-3-(benzyloxy-diisopropylamino-phosphanyloxy)-propionic acid benzyl ester 
• 77870-99-6 ester benzylique de la N-(benzyloxycarbonyl)-O-(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-L-serine 
• 77870-98-5 ester benzylique de la N-(benzyloxycarbonyl)-O-(2,3,4-tri-O-benzyl-α-D-xylopyranosyl)-L-serine 
• 83956-35-8 3-O-(6-O-Acetyl-2-azido-4-O-benzyl-2-desoxy-3-O-trichloracetyl-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serinbenzylester 

Relevant articles and documents

PROCESS FOR PRODUCING TCA CYCLE INTERMEDIATE CONJUGATES AND POLYMORPHS OF A TCA CYCLE INTERMEDIATE CONJUGATE

The invention provides a process for preparing a TCA cycle intermediate conjugated to an amino acid having the structure of a compound of Formula (X). In addition, the invention also provides polymorphs of the compound of Formula (X), pharmaceutical compositions containing the compound of Formula (X), and methods treating conditions in a subject by providing compositions containing the compound of Formula (X).

Visible Light Enables Aerobic Iodine Catalyzed Glycosylation

A versatile protocol for light induced catalytic activation of thioglycosides using iodine as an inexpensive and readily available photocatalyst was developed. Oxygen serves as a green and cost-efficient terminal oxidant and irradiation is performed with a common household LED-bulb. The scope of this glycosylation protocol was investigated in the synthesis of O-glycosides with yields up to 95 %.

Toward aplyronine payloads for antibody-drug conjugates: Total synthesis of aplyronines A and D

The aplyronines are a family of antimitotic marine macrolides that disrupt cytoskeletal dynamics by dual targeting of both actin and tubulin. Given their picomolar cytotoxicity profile and unprecedented mode of action, the aplyronines represent an excellent candidate as a novel payload for the development of next-generation antibody-drug conjugates (ADCs) for cancer chemotherapy. Enabled by an improved second-generation synthesis of the macrolactone core 5, we have achieved the first total synthesis of the most potent congener aplyronine D together with a highly stereocontrolled synthesis of aplyronine A. To facilitate step economy, an adventurous site-selective esterification of the C7 hydroxyl group was performed to install the N,N,O-trimethylserine pharmacophore to directly afford aplyronines A and D. Toward the assembly of ADCs incorporating an aplyronine warhead, the C29-ester derivative 4 featuring an Fmoc-amino substituted linker attached to the actin-binding tail region was also prepared by adapting this flexible endgame.

Optimized synthesis of phosphatidylserine

The synthesis of phosphatidyl serine containing saturated fatty acids was thoroughly studied and optimized in order to establish a protocol amenable to large-scale synthesis. The key step was a one-pot multicomponent reaction involving an O-benzyl phosphorodiamidite, protected serine and diacylglycerol, followed by in situ oxidation of the resulting phosphite. In order to replace expensive and poorly stable tetrazole, a screening of substitutes was carried out and imidazolium chloride was selected as the best suited one. Springer-Verlag 2010.

Synthesis of bis-(2,3,4,6-tetra-O-acetyl-α-d-mannopyranosyl)-l-serinyl phosphate, as a prodrug of mannose-1-phosphate

An efficient synthesis of di-mannosyl serinyl phosphate using a convergent strategy involving a silver assisted nucleophilic substitution of tetra-O-acetyl-α-d-mannopyranosyl bromide by a conveniently protected O-serinyl phosphate is described. The straightforward synthesis of phosphoserine under Mitsunobu conditions is also reported.

Utility of tetrathiomolybdate and tetraselenotungstate: Efficient synthesis of cystine, selenocystine, and their higher homologues

Efficient synthesis of cystine, selenocystine, and their higher homologues like homo and bishomo amino acid derivatives from natural amino acid derivatives using tetrathiomolybdate and tetraselenotungstate reagents under mild and neutral conditions is reported. The generality of the reaction has been studied by capping various groups to amino and carboxyl components of canonical amino acids.

Broadening of the substrate tolerance of α-chymotrypsin by using the carbamoylmethyl ester as an acyl donor in kinetically controlled peptide synthesis

In the kinetically controlled approach of peptide synthesis mediated by α-chymotrypsin, the broadening of the protease's substrate tolerance is achieved by switching the acyl donor from the conventional methyl ester to the carbamoylmethyl ester. Thus, as a typical example, the extremely low coupling efficiency obtained by employing the methyl ester of an inherently poor amino acid substrate, Ala, is significantly improved by the use of this particular ester. Its ameliorating effect is observed also in the couplings of other amino acid residues such as Gly and Ser as carboxy components.

The synthesis and properties of Gla- and Phe-containing analogues of cyclic RGD pentapeptides

Cyclopentapeptides containing the Arg-Gly-Asp motif have been synthesised using solid-phase assembly of side-chain-protected linear precursors, followed by solution-phase cyclisation. The replacement of the Asp residue by γ-carboxyglutamic acid (Gla) is a novel feature which gives rise to an analogue which inhibits cell adhesion, yet its congeners do not show activity in binding assays with recombinant integrin receptors. NMR techniques support a β/γ-turn conformation in most of the analogues. The Royal Society of Chemistry 2000.

Wittig reaction with N-protected 3-(triphenylphosphonio)alaninates: Synthesis of optically active (E)-(2-arylvinyl)glycine derivatives

(R)-[2-Carboxy-2-[(methoxycarbonyl)amino]ethyl]triphenylphosphonium chloride (1) was converted by treatment with anion exchange resin (HCO3-) into the inner salt 13h, which gave a better yield (43%) than 1 in the Wittig reaction with benzaldehyde to afford the [S-(E)]-(2-phenylvinyl)glycine derivative 24. The inner salt 13i bearing an N-benzyioxycarbonyl group was prepared by hydrogenolysis of (R)-[3-benzyloxy-2-[(benzyloxycarbonyl)amino]-3-oxopropyl]triphenylpho sphonium chloride (11e) over palladium on carbon, followed by dehydrochlorination. Hydrogenolysis of 11e over Pearlman's catalyst afforded the unprotected phosphonium chloride 12 (X = Cl). N-tert-Butoxycarbonylation of 12 followed by dehydrochlorination afforded 13j, which was more efficiently prepared through hydrogenolysis of (R)-[3-benzyloxy-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl]triphenylp hosphonium chloride (11f). The usefulness of 13h-j as building blocks for the synthesis of configurationally labile (2-arylvinyl)glycine derivatives was exemplihed by the Wittig reactions with piperonal, which exclusively afforded the (E)-isomers 18h-j with high optical purity in 28-39% yield.