93527-54-9

Usage

Uses

Used in Pharmaceutical Industry:
O-tert-Butyl-trans-4-hydroxy-L-prolinetert-butyl is utilized as a key building block in the synthesis of various drugs. Its protective function for the hydroxy group of proline enables the development of peptide-based drugs and pharmaceutical intermediates, contributing to the advancement of medicinal chemistry.
Used in Peptide Synthesis:
In the field of peptide synthesis, O-tert-Butyl-trans-4-hydroxy-L-prolinetert-butyl acts as a protecting group for the hydroxy functionality of proline residues. This selective protection is crucial for enabling specific reactions to occur without unwanted side reactions, thus facilitating the synthesis of complex peptide structures with greater precision and control.

Upstream product

• 96167-96-3 Z-L-Hyp(tBu)-OtBu 
• 13504-85-3 Z-L-Hyp-OH 

Downstream Products

• 119071-05-5 Z-L-Val-L-Hyp(tBu)-OtBu 
• 263846-91-9 C₇₈H₁₀₃N₉O₁₃ 
• 263846-89-5 C₇₀H₈₈N₈O₁₁ 
• 263846-92-0 1-(2-{5-{[1-(2-amino-3-tert-butoxy-butyryl)-4-azido-pyrrolidine-2-carbonyl]-amino}-2-[(4''-pentyloxy-[1,1';4',1'']terphenyl-4-carbonyl)-amino]-pentanoylamino}-3-tert-butoxy-butyryl)-4-tert-butoxy-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 263846-90-8 (2S,4R)-1-((2S,3R)-2-{(S)-5-[((2S,4S)-4-Azido-pyrrolidine-2-carbonyl)-amino]-2-[(4''-pentyloxy-[1,1';4',1'']terphenyl-4-carbonyl)-amino]-pentanoylamino}-3-tert-butoxy-butyryl)-4-tert-butoxy-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 263846-87-3 TerOrn(Z)-Thr(Ot-Bu)-Pro(Ot-Bu) 
• 263846-88-4 1-(2-{5-amino-2-[(4''-pentyloxy-[1,1';4',1'']terphenyl-4-carbonyl)-amino]-pentanoylamino}-3-tert-butoxy-butyryl)-4-tert-butoxy-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 263846-85-1 1-{2-[5-benzyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanoylamino]-3-tert-butoxy-butyryl}-4-tert-butoxy-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 263846-86-2 1-[2-(2-amino-5-benzyloxycarbonylamino-pentanoylamino)-3-tert-butoxy-butyryl]-4-tert-butoxy-pyrrolidine-2-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

Regioselective acylation of octyl β-D-glucopyranoside by chiral 4-pyrrolidinopyridine analogues

Chiral 4-pyrrolidinopyridine (PPY) analogues with dual functional side chains consisting of indole units have been prepared from trans-4-hydroxy-L- proline. Treatment of octyl β-D-glucopyranoside with isobutyric anhydride in the presence of the catalysts gave the 6-O-acylate as the major product via acylation of a primary hydroxyl group. On the other hand, the 4-O-acylate was obtained as the major product in 66% regioselectivity via acylation of the secondary hydroxyl group at C-4 on treatment of octyl β-D-glucopyranoside with isobutyric anhydride in the presence of a PPY catalyst. Use of isobutyryl chloride instead of isobutyric anhydride in the presence of the catalyst gave the 6-O-acylate in 87% regioselectivity. Georg Thieme Verlag Stuttgart.

Preparation and properties of chiral 4-pyrrolidinopyridine (PPY) analogues with dual functional side chains

Chiral 4-pyrrolidinopyridine analogues 8-13 with two distinct functional side chains at C(2) and C(4) of the pyrrolidine ring were prepared from 4-hydroxy-L-proline. We examined desymmetrization of meso-1,3-cyclohexanediol through enantioselective acylation using these catalysts and found that introduction of a C(4)-side chain was effective for improving both the chemo- and enantioselectivity of acylation.

The Dipeptide Antibiotic N-Valyl-dihydroxyhomoproline: Isolation, Characterization, and Antimicrobial Activities

The dipeptide antibiotic N-valyl-dihydroxyhomoproline (Val-Dhp, 1) was isolated from the culture filtrate of Streptomyces antibioticus ssp. antibioticus Tue 1718 by gel chromatography and HPLC.The purification, chemical, and spectroscopic characterization