H-Cys(Trt)-OH | NSC 83265 | Kinesin

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Quality Control of H-Cys(Trt)-OH Purity: 99% SDS Specification

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Product Details of H-Cys(Trt)-OH

CAS No. :	2799-07-7
Formula :	C₂₂H₂₁NO₂S
M.W :	363.47
SMILES Code :	C(SC[C@@H](C(O)=O)N)(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
Synonyms :	NSC 83265; S-Tritylcysteine; H-L-Cys(Trt)-OH
MDL No. :	MFCD00002611

Safety of H-Cys(Trt)-OH

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of H-Cys(Trt)-OH

* 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.

Downstream synthetic route of [ 2799-07-7 ]

[ 2799-07-7 ] Synthesis Path-Downstream 1~35

1
[ 24424-99-5 ]
[ 2799-07-7 ]
[ 21947-98-8 ]

Yield	Reaction Conditions	Operation in experiment
90%		To a solution of 2[36] and [37] (5 g, 12.7 mmol) in NaOH 2N (80 mL) was added Boc2O (4.5 g, 20 mmol) and the reaction mixture was stirred at room temperature for 24 h. The aqueous solution was then acidified with HCl concentrated until pH 2 and extracted with CH2Cl2 (2 .x. 100 mL); the combined organic phases were washed with brine, dried and concentrated under reduce pressure to give without any further purification compound 3 (5.3 g, 90percent) as white foam.1H NMR (DMSO): delta (ppm) 1.37 (s, 9H, 3 .x. CH3); 2.29-2.58 (m, 2H, CH2); 3.76-3.79 (m, 1H, CH); 6.84 (d, J = 7.8 Hz, 1H, NH); 7.14-7.38 (m, 15H, trityl-H).MALDI-TOF MS: m/z 464.8 Da [M + H], C27H29NO4S, Mol. Wt.: 463.59.
86.21%	With sodium hydroxide; In 1,4-dioxane; water; at 20℃; for 8h;Cooling with ice;	The compound <strong>[2799-07-7]S-trityl-L-cysteine</strong> (5 g, 13.76 mmol)Was dissolved in dioxane (40 ml)Water (20 ml),1M sodium hydroxide solution (14 ml)Stir under ice bath,Boc-anhydride (3.5 ml, 15.14 mmol) was added,The reaction naturally rose to room temperature,Stirring for 8 hours,TLC detection reaction is completed,The reaction mixture was concentrated to 20-25 ml,Ethyl acetate was added,A solution of sodium bisulfate was added dropwise under stirring in an ice bath,After adjusting the pH to 2-3,Extracted with ethyl acetate,The organic layer was washed with saturated brine,Then dried over sodium sulfate,concentrate,Column chromatography (methanol: dichloromethane 1percent -5percent),The product was a white solid (5.5 g, yield: 86.21percent).
60%		To the solution of Trt-Cys-OH (22.68 g, 62.5 mmol) in dioxane (60 mL) and water (125 mL) was added di-tert-butyldicarbonate (41 g, 187 mmol) at 45 0C, and the solution was adjusted with NaOH(4M) until pH = 9.5, and then stirred at the same temperature overnight. Once the reaction was done, water and dioxane was removed under reduced pressure. The residue was dissolved into water (150 mL) , extracted with ethyl acetate (2 x 100 mL) . The aqueous layer was adjusted to pH = 2 with dilute HCl while in an ice bath, and then the aqueous layer was extracted with ethyl acetate. The combined ethyl acetate layers were washed with water, dried over magnesium sulfate. Removal of the solvent under vacuum yielded a yellow oil. The residue was then dissolved into ethyl ether and carefully added a 1 : 1 mixture of ethyl ether and hexane while stirring to <n="32"/>precipitate out the white solid in 60percent yield. Ic: 1H NMR (300 MHz, CDC13): deltal.46 (s, 9H), 2.69 (br, 2H), 4.21 (s, IH), 4.97 (s, IH), 7.20-7.44 (m, 15H), 10.2 (br, IH); 13C NMR (75.5 MHz, CDC13): delta 28.1, 33.5, 52.4, 144.1, 155.4, 175.1

With sodium hydroxide; at 20℃; for 24h;

(1) 1.1 g of [2799-07-7]S-trityl-L-cysteine (II), 1.0 g of di-tert-butyl dicarbonate (Boc2O) and 19 mL of 2N aqueous sodium hydroxide were mixed and allowed to react at room temperature for 24 hours. Drop to room temperature, slowly dropping 1mol / L HCl to adjust pH = 2,The aqueous layer was extracted with dichloromethane. The combined organic layers were washed with distilled water to a pH of 7. The organic layer was dried over anhydrous sodium sulfate and removed with water. The filtrate was collected by filtration and the filtrate was evaporated to remove the extractant to give a white foamy solid amino-S-Trityl-Cys (III).

References: [1]European Journal of Medicinal Chemistry,2012,vol. 50,p. 383 - 392.
[2]Chemical Communications,2013,vol. 49,p. 10808 - 10810.
[3]Patent: CN106432014,2017,A .Location in patent: Paragraph 0096; 0100; 0101; 0102; 0142; 0146; 0147; 0148.
[4]Patent: WO2009/137251,2009,A2 .Location in patent: Page/Page column 30; 31.
[5]Chemistry of Natural Compounds,1979,vol. 15,p. 471 - 476.
Khimiya Prirodnykh Soedinenii,1979,vol. 15,p. 543 - 548.
[6]Organic Letters,2005,vol. 7,p. 2615 - 2618.
[7]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 7353 - 7361.
[8]Patent: CN107434776,2017,A .Location in patent: Paragraph 0075; 0077.

2
[ 2799-07-7 ]
[ 33642-47-6 ]
[ 38757-29-8 ]

References: [1]Justus Liebigs Annalen der Chemie,1972,vol. 759,p. 114 - 120.

3
[ 2799-07-7 ]
[ 76-83-5 ]
[ 27686-50-6 ]

References: [1]Canadian Journal of Chemistry,1979,vol. 57,p. 1388 - 1396.
[2]Journal of the American Chemical Society,1962,vol. 84,p. 3887 - 3897.
[3]Liebigs Annalen der Chemie,1987,p. 1025 - 1030.

4
[ 2799-07-7 ]
[ 501-53-1 ]
[ 26311-04-6 ]

References: [1]Journal of the American Chemical Society,2012,vol. 134,p. 16891 - 16898.
[2]Journal of the American Chemical Society,1962,vol. 84,p. 3887 - 3897.

5
[ 76-83-5 ]
L-cysteine p-toluenesulfonate [ No CAS ]
[ 2799-07-7 ]

References: [1]Organic Letters,2006,vol. 8,p. 3215 - 3217.

6
[ 50-00-0 ]
[ 2799-07-7 ]
[ 166169-98-8 ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 25 - 28.

7
[ 2799-07-7 ]
[ 100-52-7 ]
(R)-2-Benzylamino-3-tritylsulfanyl-propionic acid [ No CAS ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 25 - 28.

8
[ 2799-07-7 ]
[ 75-07-0 ]
N-ethyl-S-triphenylmethyl-L-cysteine [ No CAS ]

References: [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 6090 - 6096.
[2]Tetrahedron Letters,2007,vol. 48,p. 25 - 28.

9
[ 2799-07-7 ]
[ 78-84-2 ]
(R)-2-Isobutylamino-3-tritylsulfanyl-propionic acid [ No CAS ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 25 - 28.

10
[ 2799-07-7 ]
[ 81-30-1 ]
2-(1,3,6,8-tetraoxo-1,3,6,8-tetrahydro-2-oxa-7-aza-pyren-7-yl)-3-tritylsulfanyl-propionic acid [ No CAS ]

References: [1]Journal of Organic Chemistry,2018,vol. 83,p. 11654 - 11660.
[2]Journal of Organic Chemistry,2006,vol. 71,p. 7063 - 7066.
[3]Organic and Biomolecular Chemistry,2011,vol. 9,p. 7547 - 7553.

11
[ 2799-07-7 ]
[ 81-30-1 ]
[ 910138-52-2 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 7063 - 7066.
[2]Angewandte Chemie - International Edition,2007,vol. 46,p. 194 - 197.

12
[ 2799-07-7 ]
[ 78756-28-2 ]
C₂₈H₂₄N₂O₅S₂ [ No CAS ]

References: [1]Tetrahedron,2007,vol. 63,p. 7538 - 7544.

13
[ 2799-07-7 ]
[ 98-74-8 ]
[ 948586-45-6 ]

References: [1]Tetrahedron,2007,vol. 63,p. 8164 - 8173.

14
[ 2799-07-7 ]
C₂₇H₂₂N₂S₂O₂ [ No CAS ]

References: [1]Tetrahedron,2007,vol. 63,p. 7538 - 7544.

15
[ 2799-07-7 ]
[ 948586-48-9 ]

References: [1]Tetrahedron,2007,vol. 63,p. 8164 - 8173.

16
[ 2799-07-7 ]
[ 767237-49-0 ]

References: [1]Tetrahedron,2007,vol. 63,p. 8164 - 8173.
[2]Chemical Communications,2013,vol. 49,p. 10808 - 10810.

17
[ 2799-07-7 ]
N^α-nosyl-L-valyl-S-trityl-L-cysteinyl-L-alanine-OMe [ No CAS ]

References: [1]Tetrahedron,2007,vol. 63,p. 8164 - 8173.

18
[ 2799-07-7 ]
(R)-methyl 2-(7-bromoheptanamido)-3-(tritylthio)propanoate [ No CAS ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 4579 - 4583.

19
[ 2799-07-7 ]
(R)-methyl 3-(tritylthio)-2-(5-(tritylthio)pentanamido)propanoate [ No CAS ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 4579 - 4583.

20
[ 2799-07-7 ]
[ 945031-66-3 ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 4579 - 4583.

21
[ 2799-07-7 ]
[ 945031-39-0 ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 4579 - 4583.

22
[ 2799-07-7 ]
C₃₀H₂₈O₆N₂S [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 4205 - 4212.

23
[ 2799-07-7 ]
[ 942057-11-6 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 4205 - 4212.

24
[ 2799-07-7 ]
[ 942057-06-9 ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 4205 - 4212.

25
[ 2799-07-7 ]
methyl 6-[2-(1'-allyloxycarbonylamino-2'-tritylsulfanyl-ethyl)-thiazol-4-yl]-5-(4-methoxycarbonyl-thiazol-2-yl)-3-trifluoromethanesulfonyloxy-pyridine-2-carboxylate [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 4205 - 4212.

26
[ 2799-07-7 ]
methyl 6-[2-(1'-allyloxycarbonylamino-2'-tritylsulfanyl-ethyl)-thiazol-4-yl]-5-(4-methoxycarbonyl-thiazol-2-yl)-3-trifluoromethanesulfonyloxy-pyridine-2-carboxylate [ No CAS ]

References: [1]Journal of Organic Chemistry,2007,vol. 72,p. 4205 - 4212.

27
[ 2799-07-7 ]
[ 647026-18-4 ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 4579 - 4583.
[2]Patent: WO2009/151744,2009,A1 .

28
[ 2799-07-7 ]
(R)-2-{7-[(S)-1-carboxy-2-(1-trityl-1H-imidazol-4-yl)-ethyl]-1,3,6,8-tetraoxo-3,6,7,8-tetrahydro-1H-benzo[lmn][3,8]phenanthrolin-2-yl}-3-tritylsulfanyl-propionic acid [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 7063 - 7066.

29
[ 2799-07-7 ]
Fmoc-N-methyl-Cys(Trt) [ No CAS ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 25 - 28.

30
[ 2799-07-7 ]
[ 921604-15-1 ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 25 - 28.

31
[ 2799-07-7 ]
2-[(9H-fluoren-9-ylmethoxycarbonyl)-isobutyl-amino]-3-tritylsulfanyl-propionic acid [ No CAS ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 25 - 28.

32
[ 2799-07-7 ]
2-[benzyl-(9H-fluoren-9-ylmethoxycarbonyl)-amino]-3-tritylsulfanyl-propionic acid [ No CAS ]

References: [1]Tetrahedron Letters,2007,vol. 48,p. 25 - 28.

33
[ 2799-07-7 ]
[ 906666-23-7 ]

References: [1]Organic Letters,2006,vol. 8,p. 3215 - 3217.

34
[ 2799-07-7 ]
[ 158009-01-9 ]

References: [1]Organic Letters,2005,vol. 7,p. 2615 - 2618.
[2]Journal of Organic Chemistry,1994,vol. 59,p. 3216 - 3218.

35
[ 2799-07-7 ]
S-trityl-L-cysteine tert-butyl ester hydrochloride [ No CAS ]

References: [1]Organic Letters,2005,vol. 7,p. 2615 - 2618.
[2]Journal of Organic Chemistry,1994,vol. 59,p. 3216 - 3218.

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CAS No.: 2799-07-7

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CAS No.: 2799-07-7

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Product Details of H-Cys(Trt)-OH

Safety of H-Cys(Trt)-OH

Application In Synthesis of H-Cys(Trt)-OH

[ 2799-07-7 ] Synthesis Path-Downstream 1~35

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