79950-65-5

Basic information

• Product Name: N-Boc-N'-benzyloxymethyl-L-histidine
• Synonyms: nα-boc-π-bom-l-histidine;N-ALPHA-T-BUTYKOXYCARBONYL-N-IM-BENZYLOXYMETHYL-L-HISTIDINE;Nα-Boc-N(im)-benzyloxymethyl-L-histidine;NALPHA-tert-Butoxycarbonyl-N-imidazole-(benzyloxymethyl)-L-histidine;N-(tert-Butoxy)carbonyl-N'-benzyloxymethyl-L-histidine;N-Boc-N'-benzyloxymethyl-L-histidine;N-tert-Butoxycarbonyl-N(im)-benzyloxymethyl-L-histidine;Nα-Boc-π:-Bom-L-histidine, Nα-Boc-N(im)-benzyloxymethyl-L-histidine
• CAS NO: 79950-65-5
• Molecular Formula: C₁₉H₂₅N₃O₅
• Molecular Weight: 375.42
• Product Categories: Histidine [His, H];Boc-Amino Acids and Derivative;Boc-Amino acid series
• Mol File: 79950-65-5.mol

Chemical Properties

• Melting Point: 122-125 °C
• Boiling Point: 595.3oC at 760 mmHg
• Flash Point: 313.8oC
• Appearance: White/Powder
• Density: 1.21g/cm3
• Vapor Pressure: 5.11E-15mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: 2-8°C
• PKA: 3.55±0.10(Predicted)
• CAS DataBase Reference: N-Boc-N'-benzyloxymethyl-L-histidine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-N'-benzyloxymethyl-L-histidine(79950-65-5)
• EPA Substance Registry System: N-Boc-N'-benzyloxymethyl-L-histidine(79950-65-5)

Safety Data

• WGK Germany: 3
• F: 8
• Hazardous Substances Data: 79950-65-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Boc-N'-benzyloxymethyl-L-histidine is used as a key building block in peptide synthesis for the development of peptide drugs. Its presence allows for the creation of a diverse range of peptide sequences with potential therapeutic applications.
Used in Peptide Drug Development:
N-Boc-N'-benzyloxymethyl-L-histidine is utilized as a component in the synthesis of peptide drugs, contributing to the advancement of new treatments for various diseases and conditions. Its role in peptide synthesis is essential for the fast and reliable production of these drugs, catering to the growing market demand.
Used in Research and Development:
In the field of research and development, N-Boc-N'-benzyloxymethyl-L-histidine serves as a valuable tool for scientists and researchers. It is used in the design and synthesis of novel peptide sequences, enabling the exploration of new therapeutic possibilities and the enhancement of existing peptide drugs.

InChI:InChI=1/C19H25N3O5/c1-19(2,3)27-18(25)21-16(17(23)24)9-15-10-20-12-22(15)13-26-11-14-7-5-4-6-8-14/h4-8,10,12,16H,9,11,13H2,1-3H3,(H,21,25)(H,23,24)/t16-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 4467-54-3 l-histidine methyl ester dihydrochloride 
• 20898-43-5 4-(2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-1H-imidazole-1-carboxylic acid tert-butyl ester 
• 79950-77-9 N^α-tert-Boc-N^?-<(benzyloxy)methyl>-L-histidine methyl ester 
• 83468-80-8 N(α)-t-butoxycarbonyl-N(?)-benzyloxymethyl-L-histidine methyl ester hydrochloride 

Downstream Products

• 79950-74-6 N(α)-t-butoxycarbonyl-N(?)-benzyloxymethyl-L-histidyl-L-phenylalanine methyl ester 
• 332-80-9 His(1-CH₃) 
• 83468-92-2 N(α)-t-butoxycarbonyl-N(?)-benzyloxymethyl-L-histidyl-L-tryptophan methyl ester 
• 77714-20-6 Ac-His-Trp-Ala-Val-Gly-His-Leu-Met-NH2 
• 866020-96-4 (-)-[1-(2-morpholin-4-ylethylcarbamoyl)-2-(3-benzyloxymethyl-3H-imidazol-4-yl)-(S)-1-ethyl]carbamic acid tert-butyl ester 

Relevant articles and documents

N-HETEROCYCLIC ALCOHOL DERIVATIVES

Compounds of the formula STR1 wherein R 1 is an N-heterocyclic group as defined herein, are disclosed. These compounds are inhibitors of renin and therefore useful as cardiovascular agents.

Further Studies on the Protection of Histidine Side Chains in Peptide Synthesis: The Use of the ?-Benzyloxymethyl Group

Further studies on the use in peptide synthesis of N(?)-phenacyl protection for histidine side chains have shown that whilst this prevents the side chain-induced racemization which can occur if there is a lone pair of electrons available at the ?-nitrogen, there are concomitant drawbacks.As an alternative approach to the racemisation problem, the effect of halogenation of the heterocyclic ring carbons (to diminish the availability of the ?-nitrogen lone pair) has been investigated.This gives derivatives which are convenient in both classical and solid-phase applications, the halogen modifying groups being removed at the last stage by catalytic hydrogenolysis over a rhodium catalyst.Racemization is suppressed as expected, but it is not eleminated completely: direct blockade of the ?-nitrogen appears to be indispensable for its complete prohibition.Protection of the ?-nitrogen with a benzyloxymethyl group has now been found to be much more satisfactory than the use of the phenacyl group for this purpose.A ?-benzyloxymethyl substituent not only prohibits side chain-induced racemisation but also gives derivatives with convenient physical properties which can be incorporated into well estblished classical and solid-phase strategies without the need for any novel or additional operations or changes in protocol.The protecting group is stable to basic conditions, to trifluoroacetic acid, and to aqueous solutions of carboxylic acids, but is cleaved cleanly and rapidly by hydrogen bromide in trifluoroacetic acid or by catalytic hydrogenolysis.N(α)-t-Butoxycarbonyl-N(?)-benzyloxymethyl-L-histidine has been prepared in good yield by a simple procedure from an easily accessible intermediate and isolated as a crystalline solid; its use has been demonstrated by a number of exercises including a solid-phase synthesis of 5-isoleucine-angiotensin II and a classical synthesis of trihistidine.

Protection of Histidine Side-chains with ?-Benzyloxymethyl- or ?-Bromobenzyloxymethyl-groups

N(α)-t-Butoxycarbonyl-N(?)-benzyloxymethyl-L-histidine (1) and N(α)-t-butoxycarbonyl-N(?)-4-bromobenzyloxymethyl-L-histidine (2) have been prepared and shown to be suitable derivatives for peptide synthesis with histidine; the synthetic intermediates had