128107-47-1

Basic information

• Product Name: Fmoc-O-tert-butyl-D-serine
• Synonyms: 9-FLUORENYLMETHOXYCARBONYL-O-T-BUTYL-D-SERINE;TIMTEC-BB SBB002936;N-ALPHA-FMOC-O-TERT-BUTYL-D-SERINE;N-ALPHA-FMOC-O-T-BUTYL-D-SERINE;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-O-T-BUTYL-D-SERINE;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-O-TERT-BUTYL-D-SERINE;n-(9-fluorenylmethoxycarbonyl)-o-tert-butyl-d-serine;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-O-T-BUTYL-D-SERINE
• CAS NO: 128107-47-1
• Molecular Formula: C₂₂H₂₅NO₅
• Molecular Weight: 383.44
• EINECS: 1533716-785-6
• Product Categories: Amino Acids;Serine [Ser, S];Fmoc-Amino Acids and Derivatives;Fmoc-Amino acid series
• Mol File: 128107-47-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 131℃
• Boiling Point: 578.6 °C at 760 mmHg
• Flash Point: 303.7 °C
• Appearance: /
• Density: 1.216 g/cm³
• Vapor Pressure: 3.16E-14mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: 2-8°C
• PKA: 3.44±0.10(Predicted)
• BRN: 5309984
• CAS DataBase Reference: Fmoc-O-tert-butyl-D-serine(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-O-tert-butyl-D-serine(128107-47-1)
• EPA Substance Registry System: Fmoc-O-tert-butyl-D-serine(128107-47-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 128107-47-1(Hazardous Substances Data)

Usage

Description

Fmoc-O-tert-butyl-D-serine, also known as Fmoc-D-Ser(tBu)-OH, is an amino acid derivative characterized by its white powder form. It is a crucial component in the field of chemical synthesis and peptide chemistry, playing a significant role in the development of various pharmaceutical compounds and bioactive molecules.

Uses

Used in Pharmaceutical Industry:
Fmoc-O-tert-butyl-D-serine is used as a building block for the synthesis of complex peptides and proteins. Its application is primarily due to its ability to facilitate the formation of peptide bonds, which are essential for the structure and function of proteins.
Used in Chemical Synthesis:
In the realm of chemical synthesis, Fmoc-O-tert-butyl-D-serine is utilized as a key intermediate for the production of various bioactive molecules and pharmaceutical compounds. Its unique structure allows for the creation of diverse molecular architectures, contributing to the development of novel drugs and therapeutic agents.
Used in Research and Development:
Fmoc-O-tert-butyl-D-serine is also employed in research and development settings, where it is used to study the properties and interactions of amino acids, peptides, and proteins. This knowledge is vital for understanding the underlying mechanisms of various biological processes and can lead to the discovery of new therapeutic targets and treatment strategies.
Overall, Fmoc-O-tert-butyl-D-serine is a versatile and essential compound in the fields of pharmaceuticals, chemical synthesis, and research, contributing to the advancement of scientific knowledge and the development of innovative treatments for various diseases and conditions.

InChI:InChI=1/C22H25NO5/c1-22(2,3)28-13-19(20(24)25)23-21(26)27-12-18-16-10-6-4-8-14(16)15-9-5-7-11-17(15)18/h4-11,18-19H,12-13H2,1-3H3,(H,23,26)(H,24,25)/t19-/m1/s1

Upstream product

• 17083-26-0 O-tert-butyl-L-serine methyl ester 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 

Downstream Products

• 244633-35-0 3-tert-butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid pentafluorophenyl ester 
• 439905-03-0 3-tert-butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid 4-nitro-phenyl ester 
• 912941-35-6 benzyloxycarbonylmethyl 3-O-((R)-3-benzyloxytetradecanoyl)-2-((R)-3-benzyloxytetradecanoylamino)-2-deoxy-6-O-(N-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-D-seryl)-α-D-glucopyranoside 
• 913239-43-7 [(N-o-methylbenzoyl-O-tert-butyl)-D-seryl]-L-alanine 
• 913239-44-8 [(N-o,o-dimethylbenzoyl-O-tert-butyl)-D-seryl]-L-alanine 
• 913239-41-5 [(N-p-methylbenzoyl-O-tert-butyl)-D-seryl]-L-alanine 
• 913239-32-4 [(N-benzyloxycarbonyl-O-tert-butyl)-D-seryl]-L-alanine 
• 256666-25-8 [(N-benzenesulfonyl-O-tert-butyl)-D-seryl]-L-alanine 
• 913239-38-0 [(N-p-methoxybenzenesulfonyl-O-tert-butyl)-D-seryl]-L-alanine 
• 913239-33-5 [(N-benzoyl-O-tert-butyl)-D-seryl]-L-alanine 
• 913239-39-1 [(N-p-bromobenzenesulfonyl-O-tert-butyl)-D-seryl]-L-alanine 
• 913239-40-4 [(N-p-cyanobenzenesulfonyl-O-tert-butyl)-D-seryl]-L-alanine 
• 913239-42-6 [(N-m-methylbenzoyl-O-tert-butyl)-D-seryl]-L-alanine 
• 256666-30-5 2-(3-tert-butoxy-2-phenylmethanesulfonylamino-propionylamino)-propionic acid 

Relevant articles and documents

Preparation method of fmoc-O-tert-butyl-L-serine

The invention discloses a preparation method of fmoc-O-tert-butyl-L-serine. The method comprises the steps that 1, L-serine and a methanol solution are added into a reaction container, and under stirring, SOCl2 is added dropwise for reflux reaction to obtain L-serine methyl ester hydrochloride; 2, the L-serine methyl ester hydrochloride is added into tert-butyl acetate, and a catalyst is added forreaction to obtain O-tert-butyl-L-serine methyl ester; 3, the O-tert-butyl-L-serine methyl ester is added into alkaline liquid for saponification reaction to obtain an O-tert-butyl-L-serine aqueous solution; 4, an organic solvent and NaCO3 are added into O-tert-butyl-L-serine, then fmoc n-hydroxysuccinimide este is added to adjust a pH value to be 8-10, and extraction separation is conducted to obtain the fmoc-O-tert-butyl-L-serine. In the preparation method, the L-serine, methanol and SOCl2 are adopted as raw materials, and through the reflux reaction, the L-serine methyl ester hydrochlorideis prepared; the reaction is carried out in liquid phases respectively, and is safe and pollution-free.