114684-70-7

Upstream product

• 65564-05-8 3-[(benzyloxycarbonyl)amino]propanal 
• 114684-69-4 methyl 2-(benzyloxycarbonylamino)-2-(diethyloxyphosphoryl)acetate 
• 501-53-1 benzyl chloroformate 
• 34637-22-4 3-[(N-benzyloxycarbonyl)amino]propanol 
• 54755-77-0 N-benzyloxycarbonyl-3-aminopropionic acid methyl ester 
• 261509-63-1 methyl (Z)-2-(N-Cbz)amino-5-triphenylphosphinopent-2-enoate 
• 261509-61-9 methyl (Z)-2-(N-Cbz)amino-5-tosyloxypent-2-enoate 
• 261509-60-8 methyl (Z)-2-(N-Cbz)amino-5-mesyloxypent-2-enoate 
• 139125-35-2 methyl (Z)-2-(N-Cbz)amino-5-hydroxypent-2-enoate 
• 130680-59-0 Cbz-ΔGlu-OMe 

Downstream Products

• 121592-48-1 Cbz-(Z)-ΔOrn(Cbz)-OH 
• 114684-74-1 Cbz-(Z)-ΔOrn(Cbz)NCA 
• 261509-66-4 Boc-1-Tyr(MOM)-(Z)-ΔOrn(Cbz)-OMe 
• 261509-67-5 Boc-1-Tyr(MOM)-(Z)-ΔArg(Boc2)-OMe 
• 114684-76-3 Boc-ΔOrn(Cbz)-OMe 

Relevant academic research and scientific papers

Convenient synthesis and conversion of a (Z)-α,β-didehydroornithine derivative to α,β-didehydrokyotorphin

Hydrogenolysis of the azido group of methyl (Z)-2-(N-Cbz)amino-5- azidopent-2-enoate, derived by selective reduction and azidation of the side chain carboxyl group of N-protected (Z)ΔGlu-OMe, gave (Z)-α,β- didehydroornithine derivative (7). The formed 7 was further converted to the basic (Z)-α,β-didehydroarginine and the acid containing (Z)-α,β- didehydrokyotorphin.

CONVENIENT SYNTHESES AND REACTIONS OF TWO KINDS OF BASIC α-DEHYDROAMINO ACID DERIVATIVES

Two kinds of basic N-carboxy α-dehydroamino acid anhydrides (ΔNCA) were synthesized by the cyclization of N-benzyloxycarbonyl (Cbz)-α-dehydro-ornithine and -lysine (DHA), derived from Cbz-aminoaldehydes and N-Cbz-2-(diethoxyphosphinyl)glycine esters.Moreover, facile conversion of Cbz as Nα-protecting group in DHA to Boc via ΔNCA was also successful.