35016-67-2

Basic information

• Product Name: L-Histidine, N,1-bis[(phenylmethoxy)carbonyl]-
• CAS NO: 35016-67-2
• Molecular Formula: C22H21N3O6
• Molecular Weight: 423.425
• Mol File: 35016-67-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: L-Histidine, N,1-bis[(phenylmethoxy)carbonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Histidine, N,1-bis[(phenylmethoxy)carbonyl]-(35016-67-2)
• EPA Substance Registry System: L-Histidine, N,1-bis[(phenylmethoxy)carbonyl]-(35016-67-2)

Safety Data

• Hazardous Substances Data: 35016-67-2(Hazardous Substances Data)

Usage

General Description

L-Histidine, N,1-bis[(phenylmethoxy)carbonyl]- is a compound derived from the essential amino acid L-histidine. It is commonly used in biochemical research and as a pharmaceutical intermediate. L-Histidine, N,1-bis[(phenylmethoxy)carbonyl]- is a derivative of L-histidine, which is important for the synthesis of proteins, neurotransmitters, and other important molecules in the body. The addition of the N,1-bis[(phenylmethoxy)carbonyl]- group to L-histidine may enhance its stability, solubility, or other properties, making it useful for various applications in the pharmaceutical and biotechnology industries. Its precise properties and potential uses may vary depending on the specific context and application.

Upstream product

• 71-00-1 D-Histidine 
• 501-53-1 benzyl chloroformate 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 71-00-1 L-histidine 
• 59577-41-2 1-benzyloxycarbonyloxy-1H-benzotriazole 
• 13795-24-9 benzyl 4-nitrophenyl carbonate 
• 13795-28-3 benzylpentachlorophenyl carbonate 

Downstream Products

• 108016-58-6 1,N^α-bis-benzyloxycarbonyl-L-histidyl=>L-threonyl=>L-valyl=>L-glutamic acid dimethyl ester 
• 170797-88-3 4-((S)-2-Amino-2-tert-butylcarbamoyl-ethyl)-imidazole-1-carboxylic acid benzyl ester 
• 170797-90-7 4-{(S)-2-[(6-{[Benzyloxycarbonyl-(2-benzyloxycarbonylamino-ethyl)-amino]-methyl}-pyridine-2-carbonyl)-amino]-2-tert-butylcarbamoyl-ethyl}-imidazole-1-carboxylic acid benzyl ester 
• 13056-37-6 Cbz-HisGly 
• 114380-81-3 1,N^α-bis-benzyloxycarbonyl-L-histidyl chloride ; hydrochloride 
• 40917-51-9 N^α,N^im-dicarbobenzoxy-L-histidine 2,4,5-trichlorophenyl ester 
• 103929-13-1 4-((S)-2-Benzyloxycarbonylamino-2-{(S)-1-[(S)-1-({[(S)-1-((S)-1-carbamoyl-3-methylsulfanyl-propylcarbamoyl)-3-methyl-butylcarbamoyl]-methyl}-carbamoyl)-2-phenyl-ethylcarbamoyl]-2-phenyl-ethylcarbamoyl}-ethyl)-imidazole-1-carboxylic acid benzyl ester 
• 103929-14-2 4-[(S)-2-Benzyloxycarbonylamino-2-({[(S)-1-((S)-1-carbamoyl-3-methylsulfanyl-propylcarbamoyl)-3-methyl-butylcarbamoyl]-methyl}-carbamoyl)-ethyl]-imidazole-1-carboxylic acid benzyl ester 
• 103929-15-3 Di-Z-His-Leu-Met-NH₂ 
• 138846-64-7 4-((S)-2-Benzyloxycarbonylamino-2-dodecylcarbamoyl-ethyl)-imidazole-1-carboxylic acid benzyl ester 
• 60666-46-8 N^α,N^im-dicarbobenzoxy-L-histidine pentachlorophenyl ester 
• 20531-27-5 N^α,N^im-dicarbobenzoxy-L-histidine p-nitrophenyl ester 
• 138846-63-6 4-(2-Benzyloxycarbonylamino-2-dodecylcarbamoyl-ethyl)-imidazole-1-carboxylic acid benzyl ester 
• 14997-58-1 N-[(benzyloxy)carbonyl]-L-histidine 

Relevant articles and documents

Synthesis method of N-carbobenzoxy-L-histidine

The invention provides a synthesis method of N-carbobenzoxy-L-histidine, which comprises the following steps: step S1, enabling N-carbobenzoxy succinimide to react with L-histidine, so as to generate dicarbobenzoxy-L-histidine; and step S2, removing carbobenzoxy on an imidazolyl group in the bis (carbobenzoxy)-L-histidine, so as to obtain the N-carbobenzoxy-L-histidine. According to the synthesis method disclosed by the embodiment of the invention, N-benzyloxycarbonyloxy succinimide is used for replacing benzyl chloroformate, so that the problems that an intermediate is very sticky and is difficult to purify are solved; furthermore, the intermediate obtained by the first-step reaction is good in quality and free of unnecessary byproducts, and the second-step reaction can be carried out without purification of the first-step product, so that the process is simplified; moreover, when the carbobenzoxy group on the imidazolyl group is removed in the second step, ammonia gas is creatively adopted to replace common potassium hydroxide, sodium ethoxide and the like, the reaction condition is mild, removal of the alpha-amino protecting group can be avoided, and the problem of destroying the optical rotation of the product is avoided.

ONE-POT N-PROTECTION OF AMINO ACIDS

Attention is called on the extreme simple procedure for N-protection of amino acids mediated through previous silylation.Although the methodology is known, it has rather scarcely been used.Some examples show the versatility of a one-pot procedure.Selective Boc and Z- Nα-protections of His were also worked out.