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
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)
Safety
- Safety Statements
- 22-24/25
- WGK Germany
- 3
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.
N-Bromosuccinimide Price
- Product number
- 94651
- Product name
- L-Valine benzyl ester p-toluenesulfonate salt
- Purity
- ≥98.0% (TLC)
- Packaging
- 5g
- Price
- $125
- Updated
- 2022/05/15
- Product number
- V0207
- Product name
- H-Val-OBzl·Tos-OH
- Packaging
- 5G
- Price
- $44
- Updated
- 2025/07/31
- Product number
- V0207
- Product name
- H-Val-OBzl·Tos-OH
- Packaging
- 25G
- Price
- $132
- Updated
- 2025/07/31
- Product number
- 239475
- Product name
- L-Valine benzyl ester 4-toluenesulfonate salt
- Packaging
- 5g
- Price
- $163
- Updated
- 2021/12/16
- Product number
- 291989
- Product name
- L-Valine benzyl ester 4-toluenesulfonate salt
- Packaging
- 25g
- Price
- $373
- Updated
- 2021/12/16
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
- 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
- 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
- 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