[ CAS No. 76587-61-6 ] {[proInfo.proName]}

Name: 76587-61-6|H-Cys(Trt)-OtBu|95+%
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SKU: A138002
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Quality Control of [ 76587-61-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 76587-61-6 ]

Product Details of [ 76587-61-6 ]

CAS No. :	76587-61-6	MDL No. :	MFCD28387571
Formula :	C₂₆H₂₉NO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VVIZBZVUAOGUBQ-QHCPKHFHSA-N
M.W :	419.58	Pubchem ID :	10863399
Synonyms :

Safety of [ 76587-61-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 76587-61-6 ]

* 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 [ 76587-61-6 ]
Downstream synthetic route of [ 76587-61-6 ]

[ 76587-61-6 ] Synthesis Path-Upstream 1~9

1
[ 540-88-5 ]
[ 2799-07-7 ]
[ 76587-61-6 ]

Reference： [1] Organic Preparations and Procedures International, 1999, vol. 31, # 5, p. 571 - 572
[2] Patent: WO2006/24453, 2006, A1, . Location in patent: Page/Page column 14-15

2
[ 302325-60-6 ]
[ 76587-61-6 ]

Reference： [1] European Journal of Organic Chemistry, 2007, # 36, p. 6016 - 6033

3
[ 158009-01-9 ]
[ 76587-61-6 ]

Reference： [1] Organic Letters, 2016, vol. 18, # 18, p. 4726 - 4729

4
[ 79385-60-7 ]
[ 76587-61-6 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 2040 - 2048

5
[ 21947-98-8 ]
[ 76587-61-6 ]

Reference： [1] Organic Letters, 2016, vol. 18, # 18, p. 4726 - 4729

6
[ 27686-50-6 ]
[ 76587-61-6 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 2040 - 2048

7
[ 76-83-5 ]
[ 76587-61-6 ]

Reference： [1] Synlett, 2017, vol. 28, # 15, p. 1923 - 1928

8
[ 103213-32-7 ]
[ 76587-61-6 ]

Reference： [1] Synlett, 2017, vol. 28, # 15, p. 1923 - 1928

9
[ 71432-55-8 ]
[ 2799-07-7 ]
[ 76587-61-6 ]

Reference： [1] Journal of Organic Chemistry, 1994, vol. 59, # 11, p. 3216 - 3218

[ 76587-61-6 ] Synthesis Path-Downstream 1~78

1
[ 20696-66-6 ]
[ 76587-61-6 ]
Z-Trp-Gly-Gly-Cys(Trt)-OtBu [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1980,vol. 63,p. 2358 - 2363

2
[ 71432-55-8 ]
[ 2799-07-7 ]
[ 76587-61-6 ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 3216 - 3218

3
[ 24424-99-5 ]
[ 76587-61-6 ]
[ 158009-01-9 ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 3216 - 3218

4
[ 76587-61-6 ]
C₂₈H₃₇NO₇ [ No CAS ]
[ 79385-62-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 2040 - 2048

5
[ 76587-61-6 ]
Z-Trp-Gly-Gly-Gly-OH [ No CAS ]
[ 77657-07-9 ]

Reference： [1]Helvetica Chimica Acta,1980,vol. 63,p. 2358 - 2363

6
[ 76587-61-6 ]
Z-Trp-Gly-Gly-Gly-Gly-OH [ No CAS ]
[ 77657-00-2 ]

Reference： [1]Helvetica Chimica Acta,1980,vol. 63,p. 2358 - 2363

7
[ 79385-60-7 ]
[ 76587-61-6 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 2040 - 2048

8
[ 76587-61-6 ]
[ 17388-70-4 ]
Z-Trp-Gly-Cys(Trt)-OtBu [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1980,vol. 63,p. 2358 - 2363

9
[ 540-88-5 ]
[ 2799-07-7 ]
[ 76587-61-6 ]

Yield	Reaction Conditions	Operation in experiment
	With perchloric acid; In water; at 20℃; for 24h;	EXAMPLE 2. Synthesis of sildenafil analog amide with cysteine.; The synthesis of 5-(2-ethoxy-5-(4-(hydroxycarbonyl-methyDpiperazinylsulfonyl)-phenyl)-1-methyl-3-n-propyl--l,6-dihydro-7H-pyrazol [4,3-d]pyrimidin-7-one was perfor;med according to what reported by Bell in US pat. 5,346,901 and by Kim in Biorg. Med. Chem. (2001) .pound. 3013-3021.The first step is the preparation of the ter-butyl-L-(S-trityl)cysteine.2.83 mmol of S-trityl cysteine, 18 ml of terbutylacetate and 0.27 ml of HC104 (70percent) were introduced in a 50 ml flask. The reaction was carried out at room temperature for 24 hours under nitrogen athmosphere. To the mixture, 2 0 ml of ethyl acetate and NaHC03 1M up to pH 8 were added. The precipitate was filtered and the organic phase was separated and extracted with HC1 0.5 N, dried on sodium sulphate and evaporated. The product was cromatographed on silica gel using CH2C12 with 1percent methanol as eluting solvent.In a 100 ml flask 0.9 mmol of sildenafil analog 5-(2-ethoxy-5- (4-hydroxycarbonylmethyl)piperazinylsulfonyl) -phenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one were charged with 0,9 eq. of ter-butyl-L-(S-trityl)cysteine as well as 1,5 eq. of butanol dissolved in 45 ml of CH2C12. The reaction mixture was cooled at 0 C and 1.1 eq. of dicyclohexylcarbodiimide (DCC) with 2 eq. of N-methylmorpholine were added. The mixture was stirred for 5 hours at room temperature under nitrogen. At the end of the reaction after filtration and removal of the solvent, the product was cromatographed on silica gel with dichloromethane and 1percent methanol and then washed with petrol ether.At a solution of 0.608 mmol of this product in 12 ml of CH2C12/ 2 mmol of triethylsilane and 10 ml of trifluoroacetic acid were added and the mixture was stirred at room temperature and under nitrogen athmosphere for 4 hours. The reaction was maintained at room temperature for further 4 hours. After evaporation of CH2Cl2 and trifluoroacetic acid, the solid residue was washed with ether and recrystalized with ethylacetate (melting point 166-168 °C).Anal, calcd. CsgHssNvOvSa-CFaCOOITHaO Cpercent 44.61; Hpercent 5.08; Npercent 13.01; Spercent 8.51; found Cpercent 44.99; Hpercent 4.96; Npercent 12.82; Spercent 8.49.

Reference： [1]Organic Preparations and Procedures International,1999,vol. 31,p. 571 - 572
[2]Patent: WO2006/24453,2006,A1 .Location in patent: Page/Page column 14-15

10
[ 71989-14-5 ]
[ 76587-61-6 ]
[ 581799-97-5 ]

Reference： [1]Bioorganic Chemistry,2003,vol. 31,p. 109 - 121

11
[ 76587-61-6 ]
[ 581799-98-6 ]

Reference： [1]Bioorganic Chemistry,2003,vol. 31,p. 109 - 121

12
[ 76587-61-6 ]
[ 581800-03-5 ]

Reference： [1]Bioorganic Chemistry,2003,vol. 31,p. 109 - 121

13
[ 76587-61-6 ]
[ 581800-00-2 ]

Reference： [1]Bioorganic Chemistry,2003,vol. 31,p. 109 - 121

14
[ 76587-61-6 ]
[ 581799-99-7 ]

Reference： [1]Bioorganic Chemistry,2003,vol. 31,p. 109 - 121

15
[ 76587-61-6 ]
[ 581800-01-3 ]

Reference： [1]Bioorganic Chemistry,2003,vol. 31,p. 109 - 121

16
[ 76587-61-6 ]
S-trityl-L-cysteine tert-butyl ester hydrochloride [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 3216 - 3218

17
[ 76587-61-6 ]
C₆₄H₇₈N₁₂O₁₆S₂ [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1980,vol. 63,p. 2358 - 2363
[2]Helvetica Chimica Acta,1980,vol. 63,p. 2358 - 2363

18
[ 76587-61-6 ]
(4R,16S)-16-Benzyloxycarbonylamino-6,9,12,15-tetraoxo-2-thia-5,8,11,14,25-pentaaza-tricyclo[16.7.0.0^19,24]pentacosa-1⁽¹⁸⁾,19⁽²⁴⁾,20,22-tetraene-4-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1980,vol. 63,p. 2358 - 2363

19
[ 76587-61-6 ]
(R)-2-{2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-acetylamino}-3-((R)-2-{2-[(S)-2-benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-acetylamino}-2-tert-butoxycarbonyl-ethyldisulfanyl)-propionic acid tert-butyl ester [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1980,vol. 63,p. 2358 - 2363

20
[ 76587-61-6 ]
C₆₀H₇₂N₁₀O₁₄S₂ [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1980,vol. 63,p. 2358 - 2363

21
[ 27686-50-6 ]
[ 76587-61-6 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 2040 - 2048

22
[ 76587-61-6 ]
[ 79385-61-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1981,p. 2040 - 2048

23
[ 76587-61-6 ]
[ 374776-08-6 ]
C₄₉H₅₇N₇O₇S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; dicyclohexyl-carbodiimide; In dichloromethane; butan-1-ol; at 20℃; for 5h;	EXAMPLE 2. Synthesis of sildenafil analog amide with cysteine.; The synthesis of 5-(2-ethoxy-5-(4-(hydroxycarbonyl-methyDpiperazinylsulfonyl)-phenyl)-1-methyl-3-n-propyl--l,6-dihydro-7H-pyrazol [4,3-d]pyrimidin-7-one was performed according to what reported by Bell in US pat. 5,346,901 and by Kim in Biorg. Med. Chem. (2001) £ 3013-3021.The first step is the preparation of the ter-butyl-L-(S-trityl)cysteine.2.83 mmol of S-trityl cysteine, 18 ml of terbutylacetate and 0.27 ml of HC104 (70%) were introduced in a 50 ml flask. The reaction was carried out at room temperature for 24 hours under nitrogen athmosphere. To the mixture, 2 0 ml of ethyl acetate and NaHC03 1M up to pH 8 were added. The precipitate was filtered and the organic phase was separated and extracted with HC1 0.5 N, dried on sodium sulphate and evaporated. The product was cromatographed on silica gel using CH2C12 with 1% methanol as eluting solvent.In a 100 ml flask 0.9 mmol of sildenafil analog 5-(2-ethoxy-5- (4-hydroxycarbonylmethyl)piperazinylsulfonyl) -phenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one were charged with 0,9 eq. of ter-butyl-L-(S-trityl)cysteine as well as 1,5 eq. of butanol dissolved in 45 ml of CH2C12. The reaction mixture was cooled at 0 C and 1.1 eq. of dicyclohexylcarbodiimide (DCC) with 2 eq. of N-methylmorpholine were added. The mixture was stirred for 5 hours at room temperature under nitrogen. At the end of the reaction after filtration and removal of the solvent, the product was cromatographed on silica gel with dichloromethane and 1% methanol and then washed with petrol ether.At a solution of 0.608 mmol of this product in 12 ml of CH2C12/ 2 mmol of triethylsilane and 10 ml of trifluoroacetic acid were added and the mixture was stirred at room temperature and under nitrogen athmosphere for 4 hours. The reaction was maintained at room temperature for further 4 hours. After evaporation of CH2Cl2 and trifluoroacetic acid, the solid residue was washed with ether and recrystalized with ethylacetate (melting point 166-168 C).Anal, calcd. CsgHssNvOvSa-CFaCOOITHaO C% 44.61; H% 5.08; N% 13.01; S% 8.51; found C% 44.99; H% 4.96; N% 12.82; S% 8.49.

Reference： [1]Patent: WO2006/24453,2006,A1 .Location in patent: Page/Page column 14-15

24
[ 71989-23-6 ]
[ 76587-61-6 ]
[ 1010440-47-7 ]

Reference： [1]European Journal of Organic Chemistry,2007,p. 6016 - 6033

25
[ 302325-60-6 ]
[ 76587-61-6 ]

Yield	Reaction Conditions	Operation in experiment
	With diethylamine; In N,N-dimethyl-formamide; at 20℃; for 0.0833333h;	General procedure: To a solution of 10% Et2NH in DMF (3 mL) was added Fmoc-Sec(Bzh)-OtBu (5a) (0.152 g, 0.248 mmol). After stirring for 5 min at r.t., the reaction mixture was evaporated to remove excess Et2NH. Subsequently, Boc-Sec(Bzh)-OH (6a) (0.134 g, 1.2 eq), HOBt (0.073 g, 1.8 eq), EDCI (0.090 g, 1.8 eq), and DMF (1 mL) were added to the residue, and the mixture was stirred for 2 h. The resulting solution was extracted with EtOAc. The combined organic layer was washed with saturated sodium bicarbonate, 1 M HCl, and brine, dried over magnesium sulfate, and evaporated. The obtained crude product was purified by silica gel column chromatography (CHCl3-MeOH 100:1) and then GPC to give 7a as a colorless viscous oil (0.187 g, 93%).
	With diethylamine; In dichloromethane; at 20℃; for 1h;	Fmoc-GOx-Arg(Pbf)-OCumyl (78) (256 mg, 0.30 mmol, 1.0 equiv) was dissolved in 2% TFA/CH CI (0.05 M) and stirred at room temperature for 2 h following a procedure from Beadle et a/.[SI The reaction mixture was concentrated under reduced pressure, and the resulting residue was repeatedly re-suspended in CH CI (3 x 15 mL) and the solvent removed under reduced pressure. Meanwhile, diethylamine (2.0 mL) was added to a solution of Fmoc-Cys(Trt)-OfBu (81) (0418) (298 mg, 0.45 mmol, 1.5 equiv) in CH2Cl2 (2.0 mL) and the reaction mixture was stirred at room temperature for 1 h. The mixture was concentrated under reduced pressure and the resulting residue repeatedly dissolved in CH CI (3 x 15 mL) and concentrated under reduced pressure to give the crude amine. The crude Fmoc-GOx-Arg(Pbf)-OH was dissolved in DMF (5.0 mL) and HATU (125 mg, 0.33 mmol, 1.1 equiv), diisopropylethyl-amine (204 pL, 1.20 mmol, 4.0 equiv) and the crude amine in DMF (2.0 mL) were added successively. The reaction mixture was stirred at room temperature for 48 h and the solvent removed under reduced pressure. The residue was purified by flash column chromatography (Si02, PE/EtOAc l:l->5% MeOH in CH CI ) to give tripeptide 79 (268 mg, 0.24 mmol, 79%) as a white foam;

Reference： [1]European Journal of Organic Chemistry,2007,p. 6016 - 6033
[2]Phosphorus, Sulfur and Silicon and the Related Elements,2019,vol. 194,p. 750 - 752
[3]Patent: WO2019/186174,2019,A1 .Location in patent: Page/Page column 48-49; 51

26
[ 5292-43-3 ]
[ 76587-61-6 ]
[ 1315457-40-9 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 7368 - 7370

27
[ 76587-61-6 ]
[ 1431526-28-1 ]