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
• Article Data: 9

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

Description

Z-SER-OBZL, also known as N-Benzyloxycarbonyl-L-serine benzyl ester, is a chemical compound that serves as a crucial building block in the synthesis of peptides and as a biochemical reagent. It is characterized by its white to off-white powder appearance and is further utilized in the pharmaceutical industry as an intermediate for the development of various drugs.

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 
• 100-39-0 benzyl bromide 
• 501-53-1 benzyl chloroformate 
• 100-44-7 benzyl chloride 
• 2978-10-1 O-benzyl-N,N'-diisopropylisourea 
• 2016-04-8 N,N-dimethylformamide dibenzyl acetal 
• 1738-80-3 L-serine benzyl ester p-toluenesulfonate hydrochoride 

Downstream Products

• 518335-26-7 N-benzyloxycarbonyl-O-carbamoyl-L-serine benzyl ester 
• 102559-88-6 N-benzyloxycarbonyl-O-[bis-(2-chloro-ethyl)-carbamoyl]-L-serine benzyl ester 
• 1186-34-1 L-serine ethanolamine phosphate 
• 2643-42-7 O,O'-hydroxyphosphoryl-di-L-serine 
• 1195249-63-8 N-benzyloxycarbonyl-O-diphenoxyphosphoryl-L-serine benzyl ester 
• 70751-53-0 3-O-(2,3,4-Tri-O-benzoyl-β-D-xylopyranosyl)-N-(benzyloxycarbonyl)-L-serin-benzylester 
• 113727-06-3 3-O-(2,3,4-Tri-O-acetyl-β-D-xylopyranosyl)-N-(benzyloxycarbonyl)-L-serin-benzylester 
• 118999-61-4 (S)-2-Benzyloxycarbonylamino-3-(octadecyloxy-phenoxy-phosphanyloxy)-propionic acid benzyl ester 
• 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 
• 174356-44-6 1-O- 3,4,6-tri-O-benzoyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside 
• 89077-02-1 (S)-2-Benzyloxycarbonylamino-3-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propionic acid benzyl ester 
• 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 

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).

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.

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.