Tosyl-D-valine

Base Information

• Chemical Name: Tosyl-D-valine
• CAS No.: 68005-71-0
• Molecular Formula: C12H17NO4S
• Molecular Weight: 271.337
• Hs Code.: 2935009090
• UNII: 3HUK84URC7
• Mol file: 68005-71-0.mol

Synonyms:Tosyl-D-valine;68005-71-0;Tos-D-Val-OH;N-Tosyl-D-valine;Tosyl valine, D-;N-Tosylvaline, D-;3HUK84URC7;(2R)-3-methyl-2-[(4-methylphenyl)sulfonylamino]butanoic acid;D-Valine, N-((4-methylphenyl)sulfonyl)-;(R)-3-Methyl-2-(4-methylbenzenesulfonamido)butanoic acid;(2R)-3-Methyl-2-(((4-methylphenyl)sulfonyl)amino)butanoic acid;UNII-3HUK84URC7;SCHEMBL4588942;ZYFUNXTYNIYYJI-LLVKDONJSA-N;AKOS017539629;F72775;(R)-3-methyl-2-(4-methylphenylsulfonamido)butanoic acid;(2R)-3-METHYL-2-(4-METHYLBENZENESULFONAMIDO)BUTANOIC ACID

Chemical Property of Tosyl-D-valine

Chemical Property:

• Melting Point: 136-138°C
• Boiling Point: 439.9±55.0 °C(Predicted)
• PKA: 3.45±0.10(Predicted)
• PSA: 91.85000
• Density: 1.246±0.06 g/cm3(Predicted)
• LogP: 2.85420
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 271.08782920
• Heavy Atom Count: 18
• Complexity: 377

Purity/Quality:

98%Min ^*data from raw suppliers

Tosyl-D-valine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC(C(C)C)C(=O)O
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)N[C@H](C(C)C)C(=O)O
• Uses: Tosyl-D-valine (cas# 68005-71-0) is a compound useful in organic synthesis.

Technology Process of Tosyl-D-valine

There total 18 articles about Tosyl-D-valine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

D,L-valine (516-06-3,25609-85-2,7004-03-7,921-10-8) + p-toluenesulfonyl chloride (98-59-9) → N-tosylvaline (17360-25-7,68005-71-0,32013-47-1)

Guidance literature:

With sodium hydroxide; In diethyl ether; water; at 20 ℃; for 20h;

DOI:10.1246/BCSJ.20200393

Reference yield: 99.0%

N-(p-toluenesulfonyl)-α-dehydrovaline (863912-72-5) → N-((4-methylphenyl)sulfonyl)-D-valine (68005-71-0)

Guidance literature:

With hydrogen; C₄₆H₄₆ClP₂RuS₂⁽¹⁺⁾*Cl^(1-); In ethanol; at 25 ℃; for 24h; under 5414.51 Torr; Product distribution / selectivity;

Reference yield: 72.0%

D-Val-OH (640-68-6,25609-85-2,7004-03-7,921-10-8) + p-toluenesulfonyl chloride (98-59-9) → N-((4-methylphenyl)sulfonyl)-D-valine (68005-71-0)

Guidance literature:

With triethylamine; sodium hydroxide; In water; acetone; at 0 - 20 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1055/s-0037-1610390

upstream raw materials:

(2S)-3-methyl-2-[[(4-methylphenyl)sulfonyl]amino]butanoic acid ethyl ester

L-valine

methanesulfonyl chloride

(2S,3S)-N-para-toluenesulfonyl-3-methylaziridine-2-carboxylic acid

Downstream raw materials:

N-(toluene-4-sulfonyl)-L-valine thiazol-2-ylamide

3-Methyl-N-pyrimidin-2-yl-2-(toluene-4-sulfonylamino)-butyramide

2-(N-Tos-L-Val)-aminobenzothiazole

3-(N-tosyl-DL-Val)aminocoumarin

Refernces

• 1、 Sharma, Priyanka,Awasthi, Pamita. "Synthesis, Characterization, In vivo, Molecular Docking, ADMET and HOMO-LUMO study of Juvenile Hormone Analogues having sulfonamide feature as an Insect Growth Regulators". . . Retrieved 2021/02/09.
• 2、 Konrad, David B.,Kicin, Bilal,Trauner, Dirk. "Concise Asymmetric Synthesis of Kweichowenol A". supporting information. p. 383 - 386. Retrieved 2019/02/26.