99310-01-7

Basic information

• Product Name: N-Boc-N'-benzyloxymethyl-L-histidine
• Synonyms: N-ALPHA-BOC-NIM-BENZYLOXYMETHYL-D-HISTIDINE;N-ALPHA-T-BUTOXYCARBONYL-N-PI-BENZYLOXYMETHYL-D-HISTIDINE;BOC-D-HIS(3-BOM)-OH;BOC-D-HIS(BOM)-OH;BOC-D-HISTIDINE(3-BOM)-OH;BOC-D-HIS(PI-BOM)-OH;BOC-N-P-BENZYLOXYMETHYL-D-HISTIDINE;nα-boc-π-bom-d-histidine
• CAS NO: 99310-01-7
• Molecular Formula: C19H25N3O5
• Molecular Weight: 375.42
• Product Categories: Amino Acids
• Mol File: 99310-01-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 595.3oC at 760 mmHg
• Flash Point: 313.8oC
• Appearance: White to off-white/Powder
• Density: 1.21g/cm3
• Vapor Pressure: 5.11E-15mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: -15°C
• CAS DataBase Reference: N-Boc-N'-benzyloxymethyl-L-histidine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-N'-benzyloxymethyl-L-histidine(99310-01-7)
• EPA Substance Registry System: N-Boc-N'-benzyloxymethyl-L-histidine(99310-01-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 99310-01-7(Hazardous Substances Data)

Usage

Description

N-Boc-N'-benzyloxymethyl-L-histidine, also known as BOC-D-HIS(3-BOM)-OH, is a chemical compound derived from L-histidine, an essential amino acid. It is characterized by the presence of a benzyloxy-methyl group and a Boc (tert-butyloxycarbonyl) protecting group, which are crucial for its reactivity and stability in various chemical reactions.

Uses

Used in Pharmaceutical Industry:
N-Boc-N'-benzyloxymethyl-L-histidine is used as a reactant for the synthesis of Land D-amino acid sequences in the preparation of snow flea antifreeze protein. This protein is of interest in the pharmaceutical industry due to its potential applications in the development of treatments for cryoprotectants, anti-freeze agents, and other therapeutic agents that require protection against freezing or cold-related injuries.
Additionally, the compound may be utilized in the synthesis of other bioactive peptides and proteins, given its unique structural features and reactivity. Its use in the pharmaceutical industry highlights the importance of innovative chemical compounds in drug discovery and development processes.

InChI:InChI=1/C19H25N3O5/c1-19(2,3)27-18(25)21-16(17(23)24)9-15-10-22(12-20-15)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-/m1/s1

Upstream product

• 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 
• 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 

Downstream Products

• 79950-74-6 N(α)-t-butoxycarbonyl-N(?)-benzyloxymethyl-L-histidyl-L-phenylalanine methyl ester 
• 83468-96-6 N(α)-t-butoxycarbonyl-N(?)-benzyloxymethyl-L-histidyl-N(?)-benzyloxymethyl-L-histidine methyl ester 
• 83468-95-5 N(α)-t-butoxycarbonyl-N(?)-benzyloxymethyl-L-histidyl-N(?)-benzyloxymethyl-L-histidine methyl ester 
• 6858-60-2 cyclo-(Leu-His) 

Relevant articles and documents

1,2-hydroxy phosphonates and derivatives thereof

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N-morpholino derivatives and their use as anti-hypertensive agents

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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