21753-19-5

Basic information

• Product Name: Nα-Tosyl-D-α,β-diaminopropionic Acid
• Synonyms: Nα-Tosyl-D-α,β-diaminopropionic Acid;Nα-Tosyl-L-α,β-diaminopropionic Acid;(S)-3-AMino-2-[(4-tolylsulfonyl)aMino]propionic Acid;N-2-Tosyl-L-2,3-diaMinopropionic Acid;NSC 263145
• CAS NO: 21753-19-5
• Molecular Formula: C₁₀H₁₄N₂O₄S
• Molecular Weight: 258.29416
• Product Categories: Amino Acids & Derivatives
• Mol File: 21753-19-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 225-226°C
• Boiling Point: 469.7°Cat760mmHg
• Flash Point: 237.9°C
• Appearance: /
• Density: 1.373g/cm³
• Vapor Pressure: 1.26E-09mmHg at 25°C
• Refractive Index: 1.584
• Solubility: Methanol
• PKA: 2.31±0.16(Predicted)
• CAS DataBase Reference: Nα-Tosyl-D-α,β-diaminopropionic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: Nα-Tosyl-D-α,β-diaminopropionic Acid(21753-19-5)
• EPA Substance Registry System: Nα-Tosyl-D-α,β-diaminopropionic Acid(21753-19-5)

Safety Data

• Hazardous Substances Data: 21753-19-5(Hazardous Substances Data)

Usage

Chemical Properties

White Powder

Uses

Nα-Tosyl-L-α,β-diaminopropionic Acid (cas# 21753-19-5) is a compound useful in organic synthesis.

InChI:InChI=1/C10H14N2O4S/c1-7-2-4-8(5-3-7)17(15,16)12-9(6-11)10(13)14/h2-5,9,12H,6,11H2,1H3,(H,13,14)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 36212-66-5 N²-(toluene-4-sulfonyl)-L-asparagine 

Downstream Products

• 21760-84-9 N^α-Tosyl-N^β-cyanmethyl-L-α,β-diamino-propionsaeure 
• 91338-47-5 β-Ureido-L-α-tosylamino-propionsaeure 
• 3476-23-1 β-Guanidino-L-α-tosylamino-propionsaeure 
• 84856-37-1 Nβ-(5-amino-4-chloro-6-pyrimidinyl)-α-tosyldiaminopropionic acid 
• 96846-01-4 N²-<(4-methylphenyl)sulfonyl>-2-amino-3-<<(methylamino)carbonyl>amino>propanoic acid 
• 1186-65-8 (S)-2,3-diaminopropanoic acid hydrobromide 
• 84856-44-0 Nα-tosyl-β-(6-benzylamino-9-purinyl)-α-alanine 
• 84894-28-0 Nα-tosyl-β-(6-chloro-9-purinyl)alanine 
• 84894-29-1 Nα-tosyl-β(6-amino-9-purinyl)-α-alanine 
• 163212-43-9 L 738167 
• 199853-65-1 (S)-3-(3-methylbenzyl)amino-2-(4-toluenesulfonyl)amino-1-propanol 
• 199853-71-9 ethyl (S)-N-methyl-N-{3-[N-(3-methylbenzyl)-N-trifluoroacetyl]amino-2-(4-toluenesulfonyl)amino-1-propyl}aminoacetate 
• 199853-67-3 {[[(S)-3-Hydroxy-2-(toluene-4-sulfonylamino)-propyl]-(3-methyl-benzyl)-carbamoyl]-methyl}-methyl-carbamic acid tert-butyl ester 
• 199853-69-5 (S)-3-[N-(3-methylbenzyl)-N-trifluoroacetyl]amino-2-(4-toluenesulfonyl)amino-1-propanol 

Relevant articles and documents

Development of the Hofmann rearrangement of Nα-tosylasparagine through calorimetric and NMR analysis

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A highly convergent synthesis of a fibrinogen receptor antagonist

A practical multikilogram synthesis of 2(S)-[(p-toluenesulfonyl)amino]- 3-[[[5,6,7,8-tetrahydro-4-oxo-5-[2-(piperidin-4-yl)ethyl]-4H-pyrazolo[1,5- α][1,4]diazepin-2-yl]carbonyl]amino]propionic acid pentahydrate (1), an oral fibrinogen receptor antagonist, is described. The nine-step convergent process, which afforded 1 in 37% overall yield, included pyrazole 5a and N- tosylaminoalanine 16 as key fragments. Pyrazole 5a was obtained from pyrazole-3,5-dicarboxylic acid by esterification with MeOH, alkylation/cyclization with 3-bromopropylamine, and Michael addition with 4- vinylpyridine. N-Tosylaminoalanine 16 was prepared by tosylation of asparagine, Hofmann reaction, and benzyl esterification. Saponification of pyrazole 5a, coupling of the acid with N-tosylaminoalanine 16, and Pd- catalyzed hydrogenolysis and pyridine reduction completed the synthesis.

Asymmetric synthesis of (R)-6-amino-1-methyl-4-(3-methyl- benzyl)hexahydro-1H-1,4-diazepine from L-asparagine

An efficient asymmetric synthesis of (R)-6-amino-1-methyl-4-(3- methylbenzyl)hexahydro-1H-1,4-diazepine [(R)-2] which serves as the amine part of (R)-1, a potent and selective 5-HT3 receptor antagonist, is described. Formation of the hexahydro-