146951-99-7

Usage

Uses

Used in Peptide Synthesis:
Z-Hyp(tBu)-OMe is used as a starting material or a protecting group for amino acids in various peptide synthesis reactions. Its stability and compatibility with common reagents make it a valuable component in the synthesis of peptides with specific properties and functions.
Used in Organic Chemistry:
Z-Hyp(tBu)-OMe is used as a protecting group in organic chemistry, particularly in reactions involving amino acids. Its stability allows for the selective protection of the amino group, facilitating the synthesis of complex organic molecules with controlled reactivity and selectivity.

Upstream product

• 64187-48-0 methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate 
• 115-11-7 isobutene 

Downstream Products

• 1372810-15-5 (2S,4R)-N-(benzyloxycarbonyl)-4-tert-butoxy-2-(tert-butoxymethyl)pyrrolidine 
• 1372810-14-4 (2S,4R)-N-(benzyloxycarbonyl)-4-tert-butoxy-2-(methoxymethyl)pyrrolidine 
• 1056938-94-3 (2S,4R)-N-(benzyloxycarbonyl)-4-tert-butoxy-2-(hydroxymethyl)pyrrolidine 

Relevant academic research and scientific papers

New optically active 4-alkoxyprolinol ethers derived from trans-4-Hydroxy-L-proline

(2S,4R)-trans-4-Hydroxy-L-proline has been used as thechiral-pool source in the efficient syntheses of optically active protected 4-hydroxyprolinols. After N-acyl protection andester formation, the first ether moiety was introduced maintaining the chiral

Ring-Opening Reactions of 1,2-Didehydroprolines, I. - Synthesis of 4-Hydroxyornithine and Protected 4-Amino-3-hydroxybutyronitriles

The cyclic azomethines 6a, b, d and f easily undergo ring-opening reaction with hydroxylamine and its O-alkyl derivatives leading to the oximino compounds 3a, b, d and f-i.Dissolved alkali metals in amines (Birch conditions) give satisfactory yields of reduction products with a stereochemistry depending on the substitution pattern in 3b, d, f-i.In case of 3d, the (2R,4R) stereoisomer 9b is the sole product, which can subsequently be cleaved to give 8b.Compounds 3g-i give predominantly the (2S,4R) product 8a.Acylation under alkaline conditions decarboxylates the oximino compounds 3b and d to the corresponding protected butyronitriles 14a-h.Trifluoroacetic anhydride tranforms 3b into the nitrile 14i together with the cyclization product 15.Key Words: 1,2-Didehydroprolines / Oxime reduction / Ornithine derivatives / Butyronitriles / 2-Piperidones / Proline derivatives / Amino acids