183866-91-3

Upstream product

• 768-95-6 1-adamanthanol 
• 133859-39-9 1-<(methylthio)methoxy>tricyclo<3.3.1.1^3,7>decane 
• 177093-80-0 1-Chloromethoxy-adamantane 
• 183866-90-2 (R)-3-(1-Acetyl-1H-imidazol-4-yl)-2-benzyloxycarbonylamino-propionic acid methyl ester 

Downstream Products

• 177093-74-2 (R)-3-[3-(Adamantan-1-yloxymethyl)-3H-imidazol-4-yl]-2-benzyloxycarbonylamino-propionic acid 

Relevant academic research and scientific papers

Development of a new N(π)-protecting group for histidine, N(π)-1- adamantyloxymethylhistidine

N(π)-1-adamantyloixymethylhistidine, His(N(π)-1-Adom) was prepared, and the properties of the 1-adom group were examined. 1-Adom group can be easily removed by TFA; it is stable to 20% piperidine/DMF and 1N NaOH. His(N(π+)- 1-Adom) derivatives can suppress recemization during coupling reaction. TRH was synthesized using His(N(π)-1Adom), successfully.

Amino acids and peptides. Part 45. Development of a new Nπ-protecting group of histidine, Nπ-(1-adamantyloxymethyl)-histidine, and its evaluation for peptide synthesis

Nπ-(1-Adamantyloxymethyl)histidine, His(Nπ-1-Adom), is prepared and its properties are examined. The 1-Adom group can be easily removed by trifluoroacetic acid and it is stable to 20% piperidinedimethylformamide and 1 mol dm-3 NaOH. His(Nπ-1-Adom) derivatives can suppress racemization during coupling reactions. His(Nπ-1-Adom) can be used in solid-phase peptide synthesis in combination with fluoren-9-ylmethoxycarbonyl as an Nα-protecting group. Thyrotropin-releasing hormone is successfully synthesized by using His(Nπ-1-Adom).