1872-59-9

Basic information

• Product Name: O-TERT-BUTYL-N-CARBOBENZOXY-L-SERINE METHYL ESTER
• Synonyms: Z-O-T-BUTYL-L-SERINE METHYL ESTER;Z-SER(TBU)-OME;Z-T-BUTYL-L-SERINE METHYL ESTER;O-TERT-BUTYL-N-CARBOBENZOXY-L-SERINE METHYL ESTER;O-TERT-BUTYL-N-CBZ-L-SERINE METHYL ESTER;N-ALPHA-CARBOBENZOXY-L-SERINE T-BUTYL ETHER METHYL ESTER;Butylcarbobenzoxyserinemethylester;Z-O-tert·butyl-L-serine methyl ester
• CAS NO: 1872-59-9
• Molecular Formula: C₁₆H₂₃NO₅
• Molecular Weight: 309.36
• Product Categories: Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids
• Mol File: 1872-59-9.mol
• Article Data: 6

Chemical Properties

• Melting Point: 43 °C
• Boiling Point: 437.247 °C at 760 mmHg
• Flash Point: 218.239 °C
• Appearance: /
• Density: 1.117 g/cm³
• Vapor Pressure: 7.59E-08mmHg at 25°C
• Refractive Index: 6 ° (C=2, EtOH)
• Storage Temp.: 2-8°C
• PKA: 10.50±0.46(Predicted)
• CAS DataBase Reference: O-TERT-BUTYL-N-CARBOBENZOXY-L-SERINE METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: O-TERT-BUTYL-N-CARBOBENZOXY-L-SERINE METHYL ESTER(1872-59-9)
• EPA Substance Registry System: O-TERT-BUTYL-N-CARBOBENZOXY-L-SERINE METHYL ESTER(1872-59-9)

Safety Data

• Hazardous Substances Data: 1872-59-9(Hazardous Substances Data)

Usage

General Description

O-Tert-Butyl-N-Carbobenzoxy-L-Serine Methyl Ester is a chemical compound used in organic synthesis and pharmaceutical research. It is a derivative of the amino acid serine, with a tert-butyl group and a carbobenzoxy protecting group attached to the nitrogen atom. O-TERT-BUTYL-N-CARBOBENZOXY-L-SERINE METHYL ESTER is often used as a building block for the synthesis of complex organic molecules, particularly in the development of new drugs. It is also used as a reagent in peptide chemistry, where it helps to protect and manipulate amino acid side chains during the formation of peptide bonds. Overall, O-Tert-Butyl-N-Carbobenzoxy-L-Serine Methyl Ester plays an important role in the development and production of pharmaceuticals and other biologically active compounds.

InChI:InChI=1/C16H23NO5/c1-16(2,3)22-15(19)17-13(14(18)20-4)11-21-10-12-8-6-5-7-9-12/h5-9,13H,10-11H2,1-4H3,(H,17,19)/t13-/m0/s1

Upstream product

• 1676-81-9 N-benzyloxycarbonyl-L-serine methyl ester 
• 115-11-7 isobutene 
• 507-19-7 t-butyl bromide 
• 501-53-1 benzyl chloroformate 
• 186581-53-3 diazomethane 
• 104597-98-0 (S)-2-methoxycarbonyl-1-benzyloxycarbonylaziridine 
• 75-65-0 tert-butyl alcohol 
• 1676-75-1 N-benzyloxycarbonyl-O-t-butyl-L-serine 

Downstream Products

• 248931-39-7 (S)-benzyl (1-(tert-butoxy)-3-oxopropan-2-yl)carbamate 
• 174363-87-2 methyl N-(tert-butoxycarbonyl)-O-(tert-butyl)-L-serinate 
• 18822-58-7 (S)-O-tert-butylserine 
• 18700-34-0 β--propionsaeure 
• 18700-35-1 β-(N-Z-O-tert.Butyl-L-seryloxy)-propionyl-β-(O-tert.butyl-D-seryloxy)-propionsaeure-benzylester 
• 18689-53-7 β-(N-Benzyloxycarbonyl-O-tert.butyl-L-seryloxy>-propionsaeure-benzylester 
• 18783-54-5 β-(O-tert.-Butyl-L-seryloxy)-propionyl-β-(O-tert.-butyl-D-seryloxy)-propionsaeure 
• 18689-54-8 β--propionsaeure 
• 135575-80-3 cyclo-(L-phenylalanyl-O-t-butyl-N-methyl-L-seryl) 
• 135637-74-0 cyclo-(L-phenylalanyl-O-t-butyl-N-methyl-D-seryl) 
• 136578-33-1 N-benzyloxycarbonyl-L-phenylalanyl-O-t-butyl-N-methyl-L-serine methyl ester 
• 135575-87-0 N-benzyloxycarbonyl-O-t-butyl-N-methyl-t-serine methyl ester 
• 117106-19-1 N-benzyloxycarbonyl-O-t-butyl-N-methyl-L-serine 
• 135601-87-5 O-t-butyl-N-methyl-L-serine methyl ester 

Relevant articles and documents

Zn- And Cu-catalyzed coupling of tertiary alkyl bromides and oxalates to forge challenging C?O, C?S, and C?N bonds

We describe here the facile construction of sterically hindered tertiary alkyl ethers and thioethers via the Zn(OTf)2catalyzed coupling of alcohols/phenols with unactivated tertiary alkyl bromides and the Cu(OTf)2-catalyzed thiolation of unactivated tertiary alkyl oxalates with thiols. The present protocol represents one of the most effective unactivated tertiary C(sp3)? heteroatom bond-forming conditions via readily accessible Lewis acid catalysis that is surprisingly less developed.

Anthranilimide-based glycogen phosphorylase inhibitors for the treatment of Type 2 diabetes: 2. Optimization of serine and threonine ether amino acid residues

Optimization of the amino acid residue of a series of anthranilimide-based glycogen phosphorylase inhibitors is described leading to the identification of serine and threonine ether analogs. t-Butylthreonine analog 20 displayed potent in vitro inhibition of GPa, low potential for P450 inhibition, and excellent pharmacokinetic properties.

On the Preparation of β-Amino Acids from α-Amino Acids Using the Arndt-Eistert Reaction: Scope, Limitations and Stereoselectivity. Application to Carbohydrate Peptidation. Stereoselective α-Alkylations of Some β-Amino Acids

The Arndt-Eistert homologation of α-amino acids was studied to determine the stereoselectivity in this reaction by chromatographic up-to-date analytical methods.While carbamate-protected phenylglycine was transformed to the corresponding β-amino acid methyl ester with a stereoselectivity of only 9:1, all other tested amino acid derivatives (Ala, Phe, Ser, Orn, tert-Leu and perhydro-azepine-2-carboxylic acid, suitably protected) were homologated with full retention of configuration (products 9-17).The intermediate diazo ketones 1-8 were purified and characterized by their NMR spectra.When nucleophiles derived from partially protected sugars were present during decomposition of the diazo ketones (derived from amino acids or dipeptides), a strong dependence of the yield (products 21-24) on the degree of steric hindrance of the nucleophilic OH group was observed.Two of the β-amino acids obtained from the homologation reaction were transformed to α-substituted (25-27, 31, 32) and α,α-disubstituted β-amino acid derivatives (28, 29) with excellent selctivities (in most cases, a single diastereoisomer was obtained). - Key Words: β-Amino acids, α-branched/Glycopeptides