ChemicalBook > CAS DataBase List > L-Valine benzyl ester 4-toluenesulfonate

L-Valine benzyl ester 4-toluenesulfonate

Product Name
L-Valine benzyl ester 4-toluenesulfonate
CAS No.
16652-76-9
Chemical Name
L-Valine benzyl ester 4-toluenesulfonate
Synonyms
VAL-OBZL.TOS;H-VAL-OBZL TOS;Val-OBzl Tosoh;H-VAL-OBZL·TOS;L-Val-OBzl·Tos;H-L-Val-OBzl*Tos;L-Val-OBzl·TosOH;H-VAL-OBZL TOS-OH;L-Valine benzyl este;H-VAL-OBZL P-TOSYLATE
CBNumber
CB7390775
Molecular Formula
C19H25NO5S
Formula Weight
379.47
MOL File
16652-76-9.mol
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L-Valine benzyl ester 4-toluenesulfonate Property

Melting point:
160-162 °C
alpha 
-3.7 º (c=3.2% in methanol)
Boiling point:
160-162°C
Flash point:
160-162°C
storage temp. 
Inert atmosphere,Store in freezer, under -20°C
solubility 
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
form 
Powder
Appearance
White to off-white Solid
optical activity
[α]20/D 3.7±0.3°, c = 3.2% in methanol
BRN 
3643436
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-;/s3
InChIKey
QWUQVUDPBXFOKF-XAAIUDFWNA-N
SMILES
C1(=CC=CC=C1)COC([C@@H](N)C(C)C)=O.C1(S(=O)(=O)O)C=CC(C)=CC=1 |&1:9,r|
CAS DataBase Reference
16652-76-9(CAS DataBase Reference)
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Safety

Safety Statements 
22-24/25
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
94651
Product name
L-Valine benzyl ester p-toluenesulfonate salt
Purity
≥98.0% (TLC)
Packaging
5g
Price
$125
Updated
2022/05/15
TCI Chemical
Product number
V0207
Product name
H-Val-OBzl·Tos-OH
Packaging
5G
Price
$44
Updated
2025/07/31
TCI Chemical
Product number
V0207
Product name
H-Val-OBzl·Tos-OH
Packaging
25G
Price
$132
Updated
2025/07/31
Usbiological
Product number
239475
Product name
L-Valine benzyl ester 4-toluenesulfonate salt
Packaging
5g
Price
$163
Updated
2021/12/16
Usbiological
Product number
291989
Product name
L-Valine benzyl ester 4-toluenesulfonate salt
Packaging
25g
Price
$373
Updated
2021/12/16
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L-Valine benzyl ester 4-toluenesulfonate Chemical Properties,Usage,Production

Chemical Properties

Crystalline

Uses

Val-OBzl TosOH is a L-Valine derivative useful as intermediate for the preparation of peptides.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

72-18-4

104-15-4

100-51-6

16652-76-9

GENERAL STEPS: The esterification reaction was carried out on L-amino acids, except phenylglycine, where the D-enantiomer was used. A mixture of L-valine (0.05 mol), 4-methylbenzenesulfonic acid (0.06 mol), benzyl alcohol (0.25 mol), and cyclohexane (30 mL) was refluxed for 4 hours using a Dean-Stark apparatus to separate the water with which it formed an azeotrope. After cooling the reaction mixture to room temperature, ethyl acetate (80 mL) was added. After stirring for 1 hour, the precipitate was collected by filtration and dried to give L-valyl benzyl ester p-toluenesulfonate as a white solid. Following this method, amino acids 1-6 were converted to the corresponding benzyl p-toluenesulfonate 1a-6a. benzylation of compound 7 was carried out in the same manner but in the presence of more 4-methylbenzenesulfonic acid (0.11 mol) to give di-p-toluenesulfonate 7a as a white solid. The p-toluenesulfonate 8a separated as an oil at the end of the reaction; instead of adding ethyl acetate, the supernatant was removed, the oil phase was washed with cyclohexane, and poured into an aqueous solution of dichloromethane/Na2CO3. After separation of the aqueous layer, the dichloromethane was evaporated and the residue was treated with methanol hydrochloride to give the corresponding hydrochloride salt as a white solid. The benzylation of compound 9 was prolonged overnight and at the end of the reaction, 9a separated as an oil, which was poured into dichloromethane/water. After removal of the organic layer, the aqueous phase was alkalized with NaHCO3 and extracted with ethyl acetate. The organic extract was concentrated to a small volume and a slight excess of 4-methylbenzenesulfonic acid was added to precipitate 9a as a white crystalline solid.

References

[1] Tetrahedron Letters, 2008, vol. 49, # 49, p. 6962 - 6964
[2] Journal of the Indian Chemical Society, 2001, vol. 78, # 3, p. 137 - 141
[3] Amino Acids, 2017, vol. 49, # 5, p. 965 - 974
[4] Chirality, 2012, vol. 24, # 2, p. 188 - 192
[5] European Journal of Medicinal Chemistry, 2018, vol. 157, p. 962 - 977

L-Valine benzyl ester 4-toluenesulfonate Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from L-Valine benzyl ester 4-toluenesulfonate manufacturers

Sichuan HongRi Pharma-Tech Co.,Ltd
Product
H-Val-OBzl.Tos-OH 16652-76-9
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
1T+
Release date
2024-04-09
Hangzhou ICH Biofarm Co., Ltd
Product
Valsartan Methyl Ester 16652-76-9
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99.0%min
Supply Ability
10tons
Release date
2023-07-12
Career Henan Chemical Co
Product
L-Valine benzyl ester 4-toluenesulfonate 16652-76-9
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
1ton
Release date
2018-08-09

16652-76-9, L-Valine benzyl ester 4-toluenesulfonateRelated Search:

Benzyl benzoate Benzyl alcohol Benzyl chloride SODIUM P-TOLUENESULFONATE Methyl acrylate Tris(trimethylsilyl)phosphate L-Valine p-Toluenesulfonic acid Sodium xylenesulfonate Benzyl nicotinate Sorafenib tosylate Sodium p-toluenesulfonate ALPHA-METHYL-L-TRYPTOPHAN H-VAL-PNA HCL L-Valine benzyl ester hydrochloride H-VAL-ILE-OH H-VAL-ALA-OH ALPHA-METHYL-L-VALINE HYDROCHLORIDE

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  • L-Valine benzyl ester 4-toluenesulfonate
  • H-L-Val-OBzl*Tos
  • L-VALINE BENZYL ESTER P-*TOLUENESULFONAT E CRYSTALLI
  • VAL-OBZL.TOS
  • L-Valine benzyl ester p-toluenesulfonat salt
  • 2-amino-3-methylbutanoic acid (phenylmethyl) ester
  • benzyl (2S)-2-amino-3-methylbutanoate
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  • L-Val-OBzl·Tos
  • L-Valine benzyl ester 4-toluenesulfonate salt≥ 98% (HPLC)
  • L-Val-OBzl·TosOH
  • (S)-Benzyl2-amino-3-methylbutanoate4-methylbenzenesulfonate
  • L-Valine, phenylmethyl ester, 4-methylbenzenesulfonate
  • L-Valinebenzylesterp-toluenesulfonatesal
  • L-Valine benzyl ester 4-toluenesulfonate USP/EP/BP
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  • 16652-76-9
  • CH32CHCHNH2COOCH2C6H5CH3C6H4SO3H
  • Ester
  • Specialty Synthesis
  • Peptide Synthesis
  • Valine
  • Amino Acid Derivatives
  • Amino ester
  • Valine [Val, V]
  • Amino Acid Derivatives
  • Peptide Synthesis
  • Valine
  • Amino Acids
  • I - ZPeptide Synthesis
  • Modified Amino Acids
  • Amino Acid Derivatives
  • Amino Acids