17662-84-9

Basic information

• Product Name: D-Valine benzy ester 4-methylbenzenesulfonate
• Synonyms: H-D-VAL-OBZL P-TOSYLATE;H-D-VAL-OBZL TOS-OH;D-VALINE BENZYL ESTER 4-TOLUENESULFONATE SALT;D-VALINE BENZYL ESTER P-TOSYLATE;D-VALINE-OBZL P-TOSYLATE;D-Valine benzy ester 4-methylbenzenesulfonate;D-Valine benzyl ester tosylate;D-Valine Benzyl Ester p-Toluenesulfonate
• CAS NO: 17662-84-9
• Molecular Formula: C₇H₈O₃S*C₁₂H₁₇NO₂
• Molecular Weight: 379.47
• Product Categories: Amino Acid Benzyl Esters;Amino Acids;Amino Acids (C-Protected);Biochemistry
• Mol File: 17662-84-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 162 °C
• Appearance: /
• Refractive Index: 4 ° (C=3.2, MeOH)
• Storage Temp.: Store at RT.
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: D-Valine benzy ester 4-methylbenzenesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: D-Valine benzy ester 4-methylbenzenesulfonate(17662-84-9)
• EPA Substance Registry System: D-Valine benzy ester 4-methylbenzenesulfonate(17662-84-9)

Safety Data

• Hazardous Substances Data: 17662-84-9(Hazardous Substances Data)

Usage

Description

D-Valine benzy ester 4-methylbenzenesulfonate, also known as D-Valine benzyl ester p-toluenesulfonate, is a crystalline chemical compound that serves as a crucial reactant and reagent in the pharmaceutical industry. It is primarily used in the synthesis of aspartic acid protease inhibitors and plays a significant role in the development of anti-hepatitis C agents.

Uses

Used in Pharmaceutical Industry:
D-Valine benzy ester 4-methylbenzenesulfonate is used as a reactant for the synthesis of aspartic acid protease inhibitors, which are essential in the development of various therapeutic agents. These inhibitors play a vital role in modulating the activity of aspartic acid proteases, which are involved in numerous biological processes and diseases.
Additionally, D-Valine benzy ester 4-methylbenzenesulfonate is used as an important reagent in the synthesis of anti-hepatitis C agents. Hepatitis C is a viral infection that affects the liver and can lead to severe health complications. The development of effective anti-hepatitis C agents is crucial for treating and managing this disease.

InChI:InChI=1/C12H17NO2.C7H8O3S/c1-9(2)11(13)12(14)15-8-10-6-4-3-5-7-10;1-6-2-4-7(5-3-6)11(8,9)10/h3-7,9,11H,8,13H2,1-2H3;2-5H,1H3,(H,8,9,10)/t11-;/m1./s1

Upstream product

• 640-68-6 D-Val-OH 
• 104-15-4 toluene-4-sulfonic acid 
• 100-51-6 benzyl alcohol 

Downstream Products

• 79761-03-8 N-benzyloxycarbonyl-S-benzyl-L-cysteinyl-D-valine benzyl ester 
• 81306-86-7 δ-(α-benzyl, N^α-carbobenzoxy-L-α-aminoadipyl)-O-benzyl-L-seryl-D-valine benzyl ester 
• 46460-17-7 (R)-O-benzyl 2-amino-3-methylbutanoate 
• 101067-14-5 benzyl ester of N-benzyloxycarbonyl-L-seryl-D-valine 
• 79761-04-9 N-benzyloxycarbonyl-S-benzyl-L-<3-13C>cysteinyl-D-valine benzyl ester 
• 126166-73-2 N-acetyl-S-p-methoxybenzyl-(2R)-cysteinyl-(2R)-valine benzyl ester 
• 109345-41-7 N-(tert-butyloxycarbonyl)-S-benzyl-L-cysteinyl-D-valine benzyl ester 
• 81306-86-7 N-benzyloxycarbonyl-α-benzylester-δ-L-α-aminoadipoyl-O-benzyl-D-serinyl-D-valine benzylester 
• 79761-05-0 N-benzyloxycarbonyl-α-benzyl-δ-(L-α-aminoadipoyl)-S-benzyl-L-cysteinyl-D-valine benzyl ester 
• 81306-81-2 BOC-(O-benzyl)-L-seryl-D-valine benzyl ester 

Relevant articles and documents

Enantiomeric resolution of p-toluenesulfonate of valine benzyl ester by preferential crystallizaion

Preferential crystallization of amino acid derivatives by seeding a pure enantiomer into racemic amino acid solutions has been studied for many years. However, few examples of valine derivatives have been reported so far. Although there have been some reports using valine hydrogen chloride with preferential crystallization, it is difficult to obtain optical isomers for valine derivatives using preferential crystallization. In this study, repeated preferential crystallization of p-toluenesulfonate valine benzyl ester with a 20% e.e. in 2-propanol gave a 94% e.e. on sonication. Sonication accelerated crystallization rate, but there was not a big difference in e.e. between with and without sonication. However, this research demonstrates the first preferential crystallization of p-toluenesulfonate of valine benzyl esters with an acceleration of crystallization using sonication.