93527-54-9

Basic information

• Product Name: O-tert·Butyl-trans-4-hydroxy-L-prolinetert·butyl
• Synonyms: O-tert·Butyl-trans-4-hydroxy-L-prolinetert·butyl;IJUAAJVHHGZRGD-OLZOCXBDSA-N
• CAS NO: 93527-54-9
• Molecular Formula: C₁₃H₂₅NO₃
• Molecular Weight: 243.34
• Mol File: 93527-54-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 76-78 °C(Press: 0.1 Torr)
• Appearance: /
• Density: 0.99±0.1 g/cm3(Predicted)
• PKA: 7.38±0.10(Predicted)
• CAS DataBase Reference: O-tert·Butyl-trans-4-hydroxy-L-prolinetert·butyl(CAS DataBase Reference)
• NIST Chemistry Reference: O-tert·Butyl-trans-4-hydroxy-L-prolinetert·butyl(93527-54-9)
• EPA Substance Registry System: O-tert·Butyl-trans-4-hydroxy-L-prolinetert·butyl(93527-54-9)

Safety Data

• Hazardous Substances Data: 93527-54-9(Hazardous Substances Data)

Usage

General Description

O-tert-butyl-trans-4-hydroxy-L-prolinetert-butyl, also known as Boc-trans-4-hydroxy-L-proline, is a chemical compound used in the synthesis of pharmaceuticals and related products. It is a derivative of proline, an amino acid, and is often used as a protecting group in peptide synthesis. The tert-butyl group in the molecule provides protection for the hydroxy group of the proline, allowing for selective reactions in the synthesis process. O-tert·Butyl-trans-4-hydroxy-L-prolinetert·butyl is commonly used in the pharmaceutical industry to create various drugs and is an important building block for the production of peptide-based drugs and pharmaceutical intermediates.

Upstream product

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

Downstream Products

• 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 
• 119071-05-5 Z-L-Val-L-Hyp(tBu)-OtBu 

Relevant articles and documents

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.

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