88501-00-2

Basic information

• Product Name: 4-Hydroxy-L-proline benzyl ester 4-toluenesulfonate
• Synonyms: 4-Hydroxy-L-proline benzyl ester 4-toluenesulfonate;YHFQLNADHUYVAF-DHXVBOOMSA-N
• CAS NO: 88501-00-2
• Molecular Formula: C₇H₈O₃S*C₁₂H₁₅NO₃
• Molecular Weight: 0
• Product Categories: Amino Acids & Derivatives
• Mol File: 88501-00-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-Hydroxy-L-proline benzyl ester 4-toluenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-L-proline benzyl ester 4-toluenesulfonate(88501-00-2)
• EPA Substance Registry System: 4-Hydroxy-L-proline benzyl ester 4-toluenesulfonate(88501-00-2)

Safety Data

• Hazardous Substances Data: 88501-00-2(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

(2S,4R)-4-Hydroxy-proline Benzyl Ester, Toluene Sulfonic Acid Salt (cas# 88501-00-2 ) is a compound useful in organic synthesis.

Upstream product

• 331442-12-7 (trans)-1-[(1,1-dimethylethoxy)carbonyl]-4-hydroxy-L-proline 
• 104-15-4 toluene-4-sulfonic acid 
• 51-35-4 4R-4-hydroxyproline 
• 100-51-6 benzyl alcohol 

Downstream Products

• 134262-54-7 N-α-(9-fluorenylmethyloxycarbonyl)-L-trans-4-hydroxyproline benzyl ester 
• 13500-53-3 N-benzyloxycarbonyl-(2S,4R)-4-hydroxyproline benzyl ester 
• 96409-04-0 ester benzylique de la N-(chloro-2-ethyl)-N-nitrosocarbamyl-L-hydroxyproline 
• 89813-47-8 N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester 
• 108305-00-6 Boc-Gly-Pro-Hyp-OBzl 

Relevant articles and documents

Incorporation of fluoroprolines to proctolin: Study on the effect of a fluorine atom toward peptidic conformation

In spite of quite small steric perturbation, substitution of proline (Pro) in the target pentapeptide proctolin (Arg-Tyr-Leu-Pro-Thr) for (4R)- as well as (4S)-4-fluoroproline led to apparent alteration of the pyrrolidine ring structure which eventually r

Regioselective enolization and alkylation of 4-oxo-N-(9-phenylfluoren-9-yl)proline: Synthesis of enantiopure proline-valine and hydroxyproline-valine chimeras

The regioselective enolization of 4-oxo-N-(9-phenylfluoren-9-yl)proline benzyl ester (5) followed by alkylation with different alkyl halides has been used to synthesize a variety of β-alkylproline derivatives. In particular, enolization of 5 with 400 mol % of KN(SiMe3)2 and alkylation with iodomethane provided 3,3-dimethyl-4-oxo-N-(9-phenylfluoren-9-yl)proline benzyl ester (7a) in excellent yield. Subsequent hydride reduction of ketone 7a and protecting group exchange by hydrogenation in the presence of di-tert-butyl dicarbonate provided enantiopure (2S,4R)- and (2S,-4S)-3,3-dimethyl-4-hydroxy-N-(BOC)prolines 2. Hydroxyproline-valine chimeras (2S,4R)- and (2S,4S)-2 are each synthesized from hydroxyproline in six steps and 27% respective overall yield. Deoxygenation of 3,3-dimethyl-4-hydroxy-N-(9-phenylfluoren-9-yl)proline benzyl esters 9 via their conversion to xanthates 10 followed by tributylstannane-mediated reduction provided 3,3-dimethyl-N-(9-phenylfluoren-9-yl)proline benzyl ester (11) in excellent yield. Hydrogenation of 11 with Pearlman's catalyst in the presence of di-tert-butyl dicarbonate then furnished (2S)-3,3-dimethyl-N-(BOC)proline (1) in the last step of an eight-step synthesis (41% overall yield) from hydroxyproline. Both proline-valine and hydroxyproline-valine chimeras 1 and 2 were designed to serve as tools for studying the conformational requirements of biologically active peptides.

SUBSTITUTED 4-PHENOXY OR 4-PHENYLTHIO PROLINES

This invention is directed to substituted 4-phenoxy and 4-phenylthio prolines of the formula STR1 which possess useful hypotensive activity.