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Chemical Structure| 76587-61-6 Chemical Structure| 76587-61-6

Structure of H-Cys(Trt)-OtBu
CAS No.: 76587-61-6

Chemical Structure| 76587-61-6

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Product Details of [ 76587-61-6 ]

CAS No. :76587-61-6
Formula : C26H29NO2S
M.W : 419.58
SMILES Code : O=C(OC(C)(C)C)[C@@H](N)CSC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
MDL No. :MFCD28387571
InChI Key :VVIZBZVUAOGUBQ-QHCPKHFHSA-N
Pubchem ID :10863399

Safety of [ 76587-61-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

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.

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

[ 76587-61-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 71432-55-8 ]
  • [ 2799-07-7 ]
  • [ 76587-61-6 ]
  • 2
  • [ 540-88-5 ]
  • [ 2799-07-7 ]
  • [ 76587-61-6 ]
YieldReaction ConditionsOperation 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.
 

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