[ CAS No. 2485-62-3 ] {[proInfo.proName]}

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Quality Control of [ 2485-62-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2485-62-3 ]

SDS Specification

Alternatived Products of [ 2485-62-3 ]

Product Details of [ 2485-62-3 ]

CAS No. :	2485-62-3	MDL No. :	MFCD00137423
Formula :	C₄H₉NO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	135.18	Pubchem ID :	-
Synonyms :

Safety of [ 2485-62-3 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P260-P264-P270-P273-P280-P301+P312+P330-P304+P312-P305+P351+P338-P314-P337+P313-P391-P501	UN#:	3082
Hazard Statements:	H302-H319-H332-H372-H400	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 2485-62-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 2485-62-3 ]
Downstream synthetic route of [ 2485-62-3 ]

[ 2485-62-3 ] Synthesis Path-Upstream 1~2

1
[ 2485-62-3 ]
[ 81905-83-1 ]
[ 141968-72-1 ]
[ 23094-69-1 ]

Reference： [1] Heterocycles, 1992, vol. 33, # 1, p. 375 - 383

2
[ 2485-62-3 ]
[ 81905-83-1 ]
[ 141968-72-1 ]
[ 141968-71-0 ]
[ 23094-69-1 ]

Reference： [1] Heterocycles, 1992, vol. 33, # 1, p. 375 - 383

[ 2485-62-3 ] Synthesis Path-Downstream 1~14

1
[ 67-56-1 ]
[ 52-90-4 ]
[ 2485-62-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrogenchloride In water Reflux;	2 2.1.2.Preparationofcysteinemethylester The proceduresofLiandShawerefollowedwithslight modification [31]. Briefly, L-cysteine(0.08mmol)wasdissolvedinmethanol (25mL),hydrochloricacid(1mL)wasaddedtotheso-lution, andthemixturewasrefluxedovernight.Themixturewasthen concentratedbyrotatoryevaporation,yieldinganoil.Theoilwastiteratedwithdiethyletheranddriedovernighttogive L-cysteinemethylesterasawhitesolid(0.135g,96%yield): 1H NMR(D2O) δ 4.53 (t,1H),3.97(s,3H),3.33-3.21(m,2H).
85%	Stage #1: methanol With acetyl chloride at 0℃; for 0.0833333h; Stage #2: L-Cysteine for 6h; Reflux;	General procedure: Acetyl chloride (1.6 mL, 22 mmol) was slowly added to anhydrous MeOH (100 mL) at 0 °C. The solution was then stirred for 5 min, followed by addition of an amino acid (D-cysteine or L-cysteine) (20 mmol). After refluxing for 6 h, the reaction mixture was cooled to room temperature, and evaporated under reduced pressure to furnish the methyl D/L-cysteinate as a white solid in yields of 90% or 85%, respectively. To the anhydrous methanol solution (1.0 mL) of the benzonitriles (1.0 mmol) and anhydrous Na2CO3 (106 mg, 1.0 mmol) the above synthesized methyl cysteinate (5.0 mmol) was added, then the resulting mixture was stirred at 80 C for 12 h, cooled to room temperature and concentrated. The crude mixture was purified by column chromatography on silica gel (PE/EA) to afford the desired 2-substituted-phenyl-4-methoxycarbonyl-4,5-dihydrothiazoles 1e-10e and 1e'-10e' in 76% to 85% yields.
	With hydrogenchloride

Reference： [1]Bianco, Christopher L.; Moore, Cathy D.; Fukuto, Jon M.; Toscano, John P. [Free Radical Biology and Medicine, 2016, vol. 99, p. 71 - 78]
[2]Tan, Fangfang; Shi, Baojun; Li, Jian; Wu, Wenjun; Zhang, Jiwen [Molecules, 2015, vol. 20, # 11, p. 20118 - 20130]
[3]Schmir,G.L. [Journal of the American Chemical Society, 1965, vol. 87, p. 2743 - 2751]

2
[ 2485-62-3 ]
[ 16201-96-0 ]
(3<i>S</i>)-5-oxo-6ξ-[(4-phenylazo-phenylcarbamoyl)-methyl]-thiomorpholine-3<i>r</i>-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; acetone

Reference： [1]Clark-Walker,G.D.; Robinson,H.C. [Journal of the Chemical Society, 1961, p. 2810 - 2812]

4
[ 2485-62-3 ]
[ 66863-43-2 ]
[ 900865-78-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 18h;

Reference： [1]Wu, Guofeng; Liu, Jiawang; Bi, Lanrong; Zhao, Ming; Wang, Chao; Baudy-Floc'h, Michèle; Ju, Jingfang; Peng, Shiqi [Tetrahedron, 2007, vol. 63, # 25, p. 5510 - 5528]

5
[ 25021-08-3 ]
[ 2485-62-3 ]
C₁₀H₁₄N₂O₆S [ No CAS ]

Reference： [1]Bioorganic Chemistry,2006,vol. 34,p. 424 - 444

6
[ 2485-62-3 ]
[ 921-60-8 ]
methyl-2-(L-glucopentahydroxypentyl)thiazolidine-4(R)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine at 90℃; for 1h;

Reference： [1]Location in patent: experimental part Wang, Yan-Hong; Avula, Bharathi; Fu, Xiang; Wang, Mei; Khan, Ikhlas A. [Planta Medica, 2012, vol. 78, # 8, p. 834 - 837]

7
[ 30725-00-9 ]
[ 2485-62-3 ]
[ 1334590-54-3 ]

Yield	Reaction Conditions	Operation in experiment
51%	Stage #1: 2,3-O-isopropylidene-D-ribonic-γ-lactone With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In acetonitrile Reflux; Stage #2: L-Cysteine methyl ester With pyridine In methanol; acetonitrile at 20 - 50℃;

Reference： [1]Wuttke, André; Fischer, Sebastian Nils; Nebel, Annika; Marsch, Michael; Geyer, Armin [Organic and Biomolecular Chemistry, 2016, vol. 14, # 22, p. 5032 - 5048]

8
[ 200184-61-8 ]
[ 2485-62-3 ]
C₁₅H₂₆N₂O₄S [ No CAS ]
C₁₅H₂₆N₂O₄S [ No CAS ]

Reference： [1]ChemBioChem,2016,p. 1621 - 1627

9
[ 2485-62-3 ]
[ 3130-75-4 ]
methyl 2-(4-(phthalimido-2-yl)butanamido)-3-mercaptopronoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With benzotriazol-1-ol; dicyclohexyl-carbodiimide In acetonitrile at 0 - 23℃; for 18h;	General procedure for the synthesis of methyl 2-(4-(phthalimido-2-yl)butanamido)alkyl carboxylates (14-23) General procedure: To acold solution of the amino acid ester (1.50 mmol), at - 5 °C,in MeCN (15 mL), 4-(phthalimido-2-yl)butyric acid (2)(350 mg, 1.50 mmol), HOBt (203 mg, 1.50 mmol) andN,N′-dicyclohexylcarbodiimide (DCC) (309 mg, 1.5 mmol)were added successively. The reaction mixture was stirredat 0 °C for 1 h, at 5 °C for 1 h, and at 23 °C for 16 h.Dicyclohexylurea (DCU) was filtered, and the filtrate wasevaporated to dryness and the residue was dissolved in ethylacetate, filtered, washed successively with saturated NaClsolution, 5% NaHCO3 solution, 1M HCl, followed bywashing with saturated NaCl solution and finally withwater. The residue was dried (Na2SO4), filtered, evaporatedto dryness and purified on a SiO2 column (10 g). Elutionwith MeOH (0-10) and CHCl3 as an eluent afforded thepure amide derivative.

Reference： [1]Al-Masoudi, Najim A.; Abood, Einas; Al-Maliki, Ziyad T.; Al-Masoudi, Wasfi A.; Pannecouque, Christophe [Medicinal Chemistry Research, 2016, vol. 25, # 11, p. 2578 - 2588]

10
[ 2485-62-3 ]
[ 921-60-8 ]
[ 614-69-7 ]
C₁₈H₂₆N₂O₇S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: L-Cysteine methyl ester; L-glucose In pyridine at 60℃; for 1h; Stage #2: 2-tolyl isothiocyanate In pyridine for 1h; Heating;	General procedure: Compounds 1-4 (each 0.5-2 mg) were hydrolyzed in 2 mL of 2mol/L HCl at 80 °C water-bath for 2 h. After remove the solvent, the residues were dissolved in 0.5 mL pyridine containing 5 mg of L-cysteine methyl ester. The mixtures were then kept at 60 °C water-bath for 1 h, after which O-tolyl isothiocyanate (5 mg) was added and heated for 1 h. 13 Finally, the solutions were passed through a 0.45 μm syringe filter for HPLC analysis (Agilent 1200, 250 mm x 4.6 mm i.d. Cosmosil 5C18-AR-II, acetonitrile: 0.5% aqueous trifluoroacetic acid solution 25:75, 0.8 mL/min, 250 nm).The standard solutions of glucose (5 mg) were treated as described above. The peaks of glucose derivative were observed at tR(min) : 1 D-glucose 20.23 , 2 D-glucose 20.21 ,3 D-glucose 20.18 ,4 D-glucose 20.16 (reference L-glucose 18.38, D-glucose 20.14).
	Stage #1: L-Cysteine methyl ester; L-glucose With pyridine at 60℃; for 1h; Stage #2: 2-tolyl isothiocyanate at 60℃; for 1h;	Acid hydrolysis and sugar analysis of 1 and 2 General procedure: Each compound (2.0mg) was dissolved in 10% HCl (10mL). The solution was heated to 80°C in an oil bath on a hot plate and refluxed on a hotplate magnetic stirrer for 3h. After cooling, the reaction mixture was evaporated under N2 gas, and the residue was separated by solvent-solvent partition using EtOAc and water. The aqueous phase was concentrated to dryness using N2 gas and then the residue was dissolved in pyridine (1mL) containing L-cysteine methyl ester (5mg) and heated at 60°C for 60min. After the reaction mixture was evaporated to dryness, o-toylisothiocyanate (0.1mL) was then added, and the mixture was further heated at 60°C for 60min. The final mixture was evaporated under vacuum and then directly analyzed by HPLC [(SunFire column 4.6×150mm, 5μm), isocratic elution with a mobile phase CH3CN-H2O (30-70); flow rate of 0.5min/mL; UV detection at 250nm]. The standards d-glucose and l-glucose were treated by the same reaction and chromatographic conditions. By comparing the retention times of the sugar derivatives obtained from 1 or 2 with the retention times of the thiocarbamoyl thiazolidine derivatives of standard d-glucose (tR = 28.2min) and l-glucose (tR = 28.9min), the sugar moieties in 1 and 2 were both determined to be d-glucose

Reference： [1]Meng, Fan-Cheng; Liu, Hui; Huang, Xiao-Jun; Chang, Yu; Ren, Dai; Lin, Li-Gen; Zeng, Qing-Qian; Zhang, Qing-Wen [Tetrahedron Asymmetry, 2017, vol. 28, # 12, p. 1686 - 1689]
[2]Choi, Jae Sue; Ha, Manh Tuan; Kim, Chung Sub; Kim, Jeong Ah; Lee, Tae Hyun; Min, Byung Sun; Prajapati, Ritu [Phytochemistry, 2022, vol. 197]

11
[ 25021-08-3 ]
[ 2485-62-3 ]
C₁₀H₁₄N₂O₆S [ No CAS ]
C₁₀H₁₄N₂O₆S [ No CAS ]

Reference： [1]Journal of Peptide Science,2018,vol. 24

12
[ 2485-62-3 ]
[ 3589-41-1 ]
[ 75-36-5 ]
methyl 2-[(benzylcarboxamido)methyl]-4,5-dihydrothiazole-4-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: phenylmethyl cyanomethylcarbamate; acetyl chloride In ethanol at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: L-Cysteine methyl ester With triethylamine In dichloromethane at 20℃; for 48h; Inert atmosphere;

Reference： [1]Kulén, Martina; Lindgren, Marie; Hansen, Sabine; Cairns, Andrew G.; Grundström, Christin; Begum, Afshan; Van Der Lingen, Ingeborg; Brännström, Kristoffer; Hall, Michael; Sauer, Uwe H.; Johansson, Jörgen; Sauer-Eriksson, A. Elisabeth; Almqvist, Fredrik [Journal of Medicinal Chemistry, 2018, vol. 61, # 9, p. 4165 - 4175]

13
[ 2485-62-3 ]
[ 75-36-5 ]
[ 2274-42-2 ]
methyl (4R)-2-[(methylsulfonyl)methyl]Δ²-1,3-thiazoline-4-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4165 - 4175

14
[ 2485-62-3 ]
[ 332-25-2 ]
[ 127761-77-7 ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 361 - 366

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[ CAS No. 2485-62-3 ] {[proInfo.proName]}

Quality Control of [ 2485-62-3 ]

Related Doc. of [ 2485-62-3 ]

Product Details of [ 2485-62-3 ]

Safety of [ 2485-62-3 ]

Application In Synthesis of [ 2485-62-3 ]

[ 2485-62-3 ] Synthesis Path-Upstream 1~2

[ 2485-62-3 ] Synthesis Path-Downstream 1~14

Precautionary Statements-General

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