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[ CAS No. 1197020-22-6 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1197020-22-6
Chemical Structure| 1197020-22-6
Structure of 1197020-22-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1197020-22-6 ]

CAS No. :1197020-22-6 MDL No. :MFCD08275892
Formula : C22H25NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :DSEDZIUESKRBOW-FQEVSTJZSA-N
M.W : 367.44 Pubchem ID :58903485
Synonyms :

Calculated chemistry of [ 1197020-22-6 ]

Physicochemical Properties

Num. heavy atoms : 27
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.36
Num. rotatable bonds : 10
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 104.4
TPSA : 75.63 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -4.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.62
Log Po/w (XLOGP3) : 5.02
Log Po/w (WLOGP) : 4.56
Log Po/w (MLOGP) : 3.22
Log Po/w (SILICOS-IT) : 4.13
Consensus Log Po/w : 3.91

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -4.95
Solubility : 0.00413 mg/ml ; 0.0000112 mol/l
Class : Moderately soluble
Log S (Ali) : -6.35
Solubility : 0.000165 mg/ml ; 0.000000448 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -6.48
Solubility : 0.000122 mg/ml ; 0.000000333 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 3.98

Safety of [ 1197020-22-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1197020-22-6 ]

* 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 [ 1197020-22-6 ]

[ 1197020-22-6 ] Synthesis Path-Downstream   1~21

  • 1
  • C36H56N12O10*C2HF3O2 [ No CAS ]
  • [ 1197020-22-6 ]
  • [ 1396100-79-0 ]
YieldReaction ConditionsOperation in experiment
With 4‐(4,6dimethoxy‐1,3,5‐triazin‐2‐yl)‐4‐methylmorpholinium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 16h;
  • 2
  • [ 44902-02-5 ]
  • [ 82911-69-1 ]
  • [ 1197020-22-6 ]
YieldReaction ConditionsOperation in experiment
65% With sodium carbonate; In 1,4-dioxane; water; at 20℃; The unprotected aminoheptanoic acid derivative (100 mg, 0.689 mmol, 1.00 equiv) wasdissolved in 10% Na2CO3 solution (2.0 mL) and dioxane (1.0 mL) and Fmoc-OSu (256 mg,0.759 mmol, 1.10 equiv) was added. The mixture was allowed to warm to rt and stirredovernight. The reaction was quenched by the addition of water (30 mL). The aqueous layer waswashed with diethyl ether (1 × 50 mL). The aqueous layer was acidified with HCl to pH = 2 andextracted with dichloromethane (4 × 50 mL). The combined organic phases were dried oversodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by reversedphasepreparative HPLC using linear CH3CN/H2O gradients containing 0.1% trifluoroacetic acid(TFA). Identification was carried out by ESI-ToF MS and NMR spectroscopy. The N-Fmocprotected amino acid was obtained as white solid. Yield: 165 mg (0.449 mmol, 65%).1H NMR (500 MHz, C3D6O): delta = 0.88-0.91 (m, 3 H, CH3), 1.28-1.38 (m, 4 H, (CH2)2CH3), 1.42-1.50 (m, 2 H, CH2CH2CHCO2H), 1.70-1.78 (m, 1 H, CH2CH2CHCO2H), 1.84-1.91 (m, 1 H,CH2CH2CHCO2H), 4.21-4.27 (m, 2 H, COOCH2CH), CHCO2H), 4.33 (d, J = 7.2 Hz, 2 H,COOCH2CH), 7.30-7.34 (m, 2 H, Ar), 7.39-7.42 (m, 2 H, Ar), 7.71-7.73 (m, 2 H, Ar), 7.86 (d, J =7.5 Hz, 2 H, Ar) ppm signals for NH and COOH were not found; 13C NMR (126 MHz,S18C3D6O): delta = 14.3 (CH3), 23.1 (CH2CH2CH3), 26.2 (CH2CH2CHCO2H), 32.1 (CH2CH2CH3), 32.5 (CH2CHCO2H), 48.0 (COOCH2CH), 54.7 (CHCO2H), 67.1 (COOCH2CH), 120.8 (Ar-C), 126.2 (Ar-C), 127.9 (Ar-C), 128.5 (Ar-C), 142.1 (Ar-C), 145.0 (Ar-C), 157.1 (COOCH2), 174.1 (COOH) ppm; HRMS (ESI): m/z [M + Na]+ calcd. for [C22H25NNaO4]+: 390.1676; found: 390.1684.
  • 3
  • C22H23NO4 [ No CAS ]
  • [ 1197020-22-6 ]
YieldReaction ConditionsOperation in experiment
93.5 mg With hydrogen In methanol at 20℃;
  • 4
  • [ 146549-21-5 ]
  • [ 1197020-22-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 20 °C / Inert atmosphere; Schlenk technique 2: hydrogen / methanol / 20 °C / 3102.97 Torr
  • 5
  • [ 1197020-22-6 ]
  • [ 108-24-7 ]
  • [ 134150-51-9 ]
  • [ 132388-59-1 ]
  • 4-((S)-2-acetamido-3-(((S)-1-(((S)-1,4-diamino-1,4-dioxobutan-2-yl)amino)-1-oxoheptan-2-yl)amino)-3-oxopropyl)phenyl dihydrogen phosphate [ No CAS ]
YieldReaction ConditionsOperation in experiment
26% Stage #1: L-Asn(Trt) With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 2h; Inert atmosphere; Stage #2: With piperidine; benzotriazol-1-ol In N,N-dimethyl-formamide for 0.333333h; Inert atmosphere; Stage #3: (S)-2-[((9H-Fluoren-9-yl)methoxy)carbonyl]amino}heptanoic acid; acetic anhydride; N2-<<(9H-Fluoren-9-yl)methoxy>carbonyl>-O4-<bis(benzyloxy)phosphoryl>-L-tyrosine Further stages;
YieldReaction ConditionsOperation in experiment
93.5 mg With hydrogen In methanol at 20℃; Example 1 : General procedure for the synthesis of N-Fmoc amino acid analogues General procedure: In a dry box under N2 atmosphere, a Schlenk vessel equipped with a magnetic stir bar was charged with V-Fmoc allylglycine (100 mg, 0.296 mmol), degassed DCM (6.0 mL), terminal alkene (1.48 mmol, 5 eq.) and HGII (9.29 mg, 5 mol%). The vessel was sealed, removed from the dry box and attached to a vacuum manifold. The vessel was placed under a flow of nitrogen and the quick fit stopper replaced with a suba seal pierced with a 26 gauge needle to allow a constant flow of nitrogen over the top of the reaction. The reaction was stirred at room temperature overnight allowing all of the DCM to evaporate. The residue was washed with hexane (2 x 10 mL) and collected via filtration or centrifuge. The residue was then re-dissolved in MeOH (10 mL) and transferred to a Fischer-Porter tube. The vessel was charged with H2 (60 p.s.i.), sealed and stirred at room temperature overnight. The reaction mixture was then concentrated in vacuo and the residual brown solid was purified via column chromatography to obtain pure -Fmoc amino acid analogue. Alternatively, the residual brown solid was taken up in a small quantity of Et20. Insoluble matter was removed by filtration. The filtrate was concentrated in vacuo to give an off white solid.
  • 7
  • [ 29022-11-5 ]
  • [ 35661-39-3 ]
  • [ 1197020-22-6 ]
  • [ 71989-31-6 ]
  • [ 108-24-7 ]
  • [ 71989-38-3 ]
  • [ 73731-37-0 ]
  • [ 105047-45-8 ]
  • [ 73724-45-5 ]
  • [ 91000-69-0 ]
  • [ 146982-27-6 ]
  • C68H113N21O21 [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% Stage #1: (S)-6-allyloxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid With N-ethyl-N,N-diisopropylamine Stage #2: With piperidine In N,N-dimethyl-formamide Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; (S)-2-[((9H-Fluoren-9-yl)methoxy)carbonyl]amino}heptanoic acid; Fmoc-Pro-OH; acetic anhydride; Fmoc-Tyr(tBu)-OH; Fmoc-Thr-OH; Fmoc-Lys-OH; N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine; Fmoc-L-Arg-OH Further stages;
  • 8
  • 2-aminoheptanoic acid [ No CAS ]
  • [ 1197020-22-6 ]
  • Fmoc-R-2-aminoheptanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
With OJ-H(2 x 15cm) In methanol Resolution of racemate;
  • 9
  • [ 29022-11-5 ]
  • [ 68858-20-8 ]
  • [ 35661-60-0 ]
  • [ 1197020-22-6 ]
  • [ 71989-31-6 ]
  • [ 35661-40-6 ]
  • [ 71989-33-8 ]
  • [ 71989-14-5 ]
  • [ 71989-23-6 ]
  • [ 71989-38-3 ]
  • [ 71989-26-9 ]
  • [ 103213-32-7 ]
  • [ 71989-35-0 ]
  • [ 71989-28-1 ]
  • [ 132388-59-1 ]
  • [ 109425-51-6 ]
  • [ 143824-78-6 ]
  • Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
  • DCLG-(L-cyclopentylglycinyl)-MRKCIPDNDKCCRPNLVCSRTHKWCKYVF-NH2; disulfide linked (C2→C17, C9→C23, C16→C30) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-Fmoc L-Phe With 1-[(1-(cyano-​2-​ethoxy-​2-​oxoethylidenaminooxy)​dimethylamino-​morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide Stage #2: With piperidine In N,N-dimethyl-formamide for 0.416667h; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-Leu-OH; (S)-2-[((9H-Fluoren-9-yl)methoxy)carbonyl]amino}heptanoic acid; Fmoc-Pro-OH; N-Fmoc L-Phe; Fmoc-Ser(tBu)-OH; Fmoc-(tBu)Asp-OH; Fmoc-Ile-OH; Fmoc-Tyr(tBu)-OH; Fmoc-Lys(tert-butoxycarbonyl); N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine; Fmoc-Thr(tBu)-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine; L-Asn(Trt); Fmoc-His(Trt)-OH; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine Further stages;
  • 10
  • [ 29022-11-5 ]
  • [ 68858-20-8 ]
  • [ 35661-60-0 ]
  • [ 35661-39-3 ]
  • [ 1197020-22-6 ]
  • [ 71989-14-5 ]
  • [ 71989-18-9 ]
  • [ 71989-38-3 ]
  • [ 71989-35-0 ]
  • [ 79-08-3 ]
  • [ 109425-51-6 ]
  • [ 116821-47-7 ]
  • Fmoc-D-Cys(Trt)-OH [ No CAS ]
  • [ 143824-78-6 ]
  • Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
  • [ 199110-64-0 ]
  • fmoc-S-4-methoxytrityl-L-cysteine [ No CAS ]
  • C152H213N37O38S3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.89% Stage #1: Fmoc-Thr(tBu)-OH With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 15℃; for 0.5h; Inert atmosphere; Stage #2: With piperidine In N,N-dimethyl-formamide at 15℃; for 0.5h; Inert atmosphere; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; (S)-2-[((9H-Fluoren-9-yl)methoxy)carbonyl]amino}heptanoic acid; Fmoc-(tBu)Asp-OH; Fmoc-Glu(OtBu)-OH; Fmoc-Tyr(tBu)-OH; bromoacetic acid; Fmoc-His(Trt)-OH; N-(9-fluorenylmethyloxycarbonyl)-4-aminobutyric acid; Fmoc-D-Cys(Trt)-OH; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; (S)-3-biphenyl-4-yl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid; fmoc-S-4-methoxytrityl-L-cysteine Further stages; 1 Exemplary Peptide Synthesis. Peptide were synthesized using standard Fmoc chemistry, for example: 1) Resin preparation: To the vessel containing Rink Amide MBHA Resin (0.2 mmol, 0.65 g, 0.31 mmol/g) in DMF (5 mL) with N2 bubbling at 15 oC for 30 min. Then 20% piperidine in DMF (10 mL) was added and the mixture was bubbled with N2 for 30 mins at 15 °C. Then the mixture was filtered to obtain the resin. The resin was washed with DMF (10 mL) *5 before proceeding to next step. 2) Coupling: A solution of Fmoc-Thr(tBu)-OH (3.00 eq), HBTU (2.85 eq) in DMF (5 mL) was added to the resin with N2 bubbling. Then DIEA (6.00 eq) was added to the mixture dropwise and bubbled with N2 for 30 min at 15 oC. The coupling reaction was monitored by ninhydrin test, if it showed colorless, the coupling was completed. If it showed blue or brownish red, the coupling was repeated and checked with ninhydrin test again till reaching completion. The resin was then washed with DMF (10 mL) *5. 3) De-protection: 20% piperidine in DMF (10 mL) was added to the resin and the mixture was bubbled with N2 for 30 mins at 15 °C. The resin was then washed with DMF (10 mL) *5. The De- protection reaction was monitored by ninhydrin test, if it showed blue or other brownish red, the reaction was completed. 4) Repeat Step 2 and 3 for all other amino acids: see below. 5) After the last position completed, the resin was washed with DMF (10 mL) *5, MeOH (10 mL) *5 and then dried under vacuum. After cycle 27, Fmoc group was kept on resin, and then Mmt group on Cys sidechain was removed by 2% TFA/2% TIS/DCM (2 min x 5), and then disulfide bond was formed on resin by adding 2 eq NCS and reacted for 15 min. Disulfide formation was confirmed by pilot cleavage and LCMS analysis, and then Fmoc was removed and 2-bromoacetic acid was coupled as the last residue. Peptide Cleavage and Purification: 1) Add cleavage buffer (92.5%TFA/2.5%TIS/2.5%H2O/2.5% 3-mercaptopropanoic acid, 10 mL) to the flask containing the side chain protected peptide at room temperature and stirred for 2 hr. 2) Filter and collect the filtrate. 3) The peptide is precipitated with cold isopropyl ether (100 mL) and centrifuged (3 mins at 3000 rpm). 4) Isopropyl ether washes the precipitate two additional times, and dry the crude peptide under vacuum for 2 hr, resulting in crude linear peptide (0.68 g, crude) as a white solid. 5) Crude linear peptide (0.68 g) was dissolved in MeCN/H2O (200 mL), then adjusted pH to 8 by 0.2 M NaHCO3 and stirred at 15 oC for 1 hr. The mixture was adjusted pH to 6 by 1 M HCl after the reaction was completed. The mixture was dried in lyophilization. The solution was purified by prep- HPLC (acid condition, TFA) directly to get compound 425 (6 mg, 0.89% yield, 96.6% purity) as a white solid.
  • 11
  • [ 843666-27-3 ]
  • [ 29022-11-5 ]
  • [ 68858-20-8 ]
  • [ 35661-60-0 ]
  • [ 35661-39-3 ]
  • [ 1197020-22-6 ]
  • [ 71989-14-5 ]
  • [ 71989-18-9 ]
  • C53H79N5O16 [ No CAS ]
  • [ 71989-38-3 ]
  • [ 79-08-3 ]
  • [ 109425-51-6 ]
  • Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
  • [ 199110-64-0 ]
  • fmoc-S-4-methoxytrityl-L-cysteine [ No CAS ]
  • C180H272N24O40S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: C53H79N5O16 With N-ethyl-N,N-diisopropylamine In dichloromethane at 15℃; for 2h; Inert atmosphere; Stage #2: With piperidine In N,N-dimethyl-formamide at 15℃; for 0.5h; Inert atmosphere; Stage #3: hexadecanedioic acid mono-tert-butyl ester; N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; (S)-2-[((9H-Fluoren-9-yl)methoxy)carbonyl]amino}heptanoic acid; Fmoc-(tBu)Asp-OH; Fmoc-Glu(OtBu)-OH; Fmoc-Tyr(tBu)-OH; bromoacetic acid; Fmoc-His(Trt)-OH; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; (S)-3-biphenyl-4-yl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid; fmoc-S-4-methoxytrityl-L-cysteine Further stages; 1 Exemplary Peptide Synthesis. Peptide were synthesized using standard Fmoc chemistry, for example: 1) Resin preparation: To the vessel containing CTC Resin (0.4 mmol, 0.4 g, 1.0 mmol/g, 1.2 eq) and compound 8 (350 mg, 335 umol, 1.0 eq) in DCM (3 mL) was added DIEA (4.00 eq) dropwise and mix for 2 hr with N2 bubbling at 15 oC. Then added MeOH (0.3 mL) and bubbled with N2 for another 30 mins. The resin was washed with DMF (10 mL) *5. Then 20% piperidine in DMF (10 mL) was added and the mixture was bubbled with N2 for 30 min at 15 °C. Then the mixture was filtered to obtain the resin. The resin was washed with DMF (10 mL) *5 before proceeding to next step. 2) Coupling: A solution of Fmoc-Glu-OtBu (3.00 eq), HBTU (2.85 eq) in DMF (5 mL) was added to the resin with N2 bubbling. Then DIEA (6.00 eq) was added to the mixture dropwise and bubbled with N2 for 30 min at 15 oC. The coupling reaction was monitored by ninhydrin test, if it showed colorless, the coupling was completed. If it showed blur or brownish red, the coupling was repeated and checked with ninhydrin test again till reaching completion. The resin was then washed with DMF (10 mL) *5. 3) De-protection of Fmoc: 20% piperidine in DMF (10 mL) was added to the resin and the mixture was bubbled with N2 for 30 min at 15 °C. The resin was then washed with DMF (10 mL) *5. The De- protection reaction was monitored by ninhydrin test, if it showed blue or other brownish red, the reaction was completed. 4) Repeat Step 2 for next amino acid: (No. 3, 16-(tert-butoxy)-16-oxohexadecanoic acid, in Table 2). 5) De-protection of Dde: 3% N2H4.H2O in DMF (10 mL) was added to the resin and the mixture was bubbled with N2 for 30 min at 15 °C. The resin was then washed with DMF (10 mL) *5. The De- protection reaction was monitored by ninhydrin test, and it showed blue or other brownish red, indicating that the reaction was completed. 6) Repeat Step 2 and 3 for all other amino acids: see below. 7) Coupling for the last position: A solution of 2-bromoacetic acid (4.00 eq) and DIC (4.00 eq) was added to resin and the mixture was bubbled with N2 for 20 min. The coupling reaction was monitored by ninhydrin test, if it showed colorless, the coupling was completed. The resin was then washed with DMF (10 mL) *5, MeOH (10 mL) *5, and then dried under vacuum. Peptide Cleavage and Purification: 1) Add cleavage buffer (2%TFA/2%Tis/96%DCM, 40 mL) to the flask containing the side chain protected peptide at room temperature with N2 bubbling for 20 min. 2) Filter and collect the filtrate. The clear solution is Compound 10 (335 umol) in cleavage buffer (400 mL), and is used in next step directly. [00693] Compound 10 (335 umol, 400 mL, in cleavage buffer) was diluted with MeOH (400 mL), based with TEA to pH = 8 under N2 atmosphere, then stirred at 15 oC for 2 hr. The solvent was removed under reduced pressure, and the residue was triturated in 0.1 M HCl (cold, 100 mL). After filtration, the solid was washed with H2O (50 mL), and then stirred in isopropyl ether (50 mL) for 10 min. Finally, the solid was dried under reduced pressure to get compound 11 (1.0 g, crude).
  • 12
  • [ 29022-11-5 ]
  • [ 68858-20-8 ]
  • [ 35661-60-0 ]
  • [ 35661-39-3 ]
  • [ 1197020-22-6 ]
  • Fmoc-(PEG)<SUB>10</SUB>-CH<SUB>2</SUB>CH<SUB>2</SUB>COOH [ No CAS ]
  • [ 71989-14-5 ]
  • [ 71989-38-3 ]
  • [ 79-08-3 ]
  • [ 109425-51-6 ]
  • Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
  • [ 199110-64-0 ]
  • fmoc-S-4-methoxytrityl-L-cysteine [ No CAS ]
  • C146H212BrN19O34S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: Fmoc-(PEG)<SUB>10</SUB>-CH<SUB>2</SUB>CH<SUB>2</SUB>COOH With N-ethyl-N,N-diisopropylamine In dichloromethane at 15℃; for 2h; Inert atmosphere; Stage #2: With piperidine In N,N-dimethyl-formamide at 15℃; for 0.5h; Inert atmosphere; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; (S)-2-[((9H-Fluoren-9-yl)methoxy)carbonyl]amino}heptanoic acid; Fmoc-(tBu)Asp-OH; Fmoc-Tyr(tBu)-OH; bromoacetic acid; Fmoc-His(Trt)-OH; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; (S)-3-biphenyl-4-yl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid; fmoc-S-4-methoxytrityl-L-cysteine Further stages; 1 Another exemplary Peptide Synthesis. Peptide were synthesized using standard Fmoc chemistry, for example: 1) Resin preparation: To the vessel containing CTC Resin (1.0 mmol, 1.0 g, 1.0 mmol/g) and Fmoc- PEG10-CH2CH2COOH (0.75 g, 1.0 mmol, 1.00 eq) in DCM (10 mL) was added DIEA (4.00 eq) dropwise and mix for 2 hr with N2 bubbling at 15 oC. Then added MeOH (1.0 mL) and bubbled with N2 for another 30 min. The resin was washed with DMF (20 mL) *5. Then 20% piperidine in DMF (20 mL) was added and the mixture was bubbled with N2 for 30 min at 15 °C. Then the mixture was filtered to obtain the resin. The resin was washed with DMF (20 mL) *5 before proceeding to next step. 2) Coupling: A solution of Fmoc-Cys(Mmt)-OH (2.00 eq), HBTU (1.90 eq) in DMF (5 mL) was added to the resin with N2 bubbling. Then DIEA (4.00 eq) was added to the mixture dropwise and bubbled with N2 for 30 min at 15 oC. The coupling reaction was monitored by ninhydrin test, if it showed colorless, the coupling was complete. If it showed blue or brownish red, the coupling was repeated and then checked with ninhydrin test again till reaching completion. The resin was then washed with DMF (10 mL) *5. 3) De-protection: 20% piperidine in DMF (10 mL) was added to the resin and the mixture was bubbled with N2 for 30 min at 15 °C. The resin was then washed with DMF (10 mL) *5. The De- protection reaction was monitored by ninhydrin test, if it showed blue or other brownish red, the reaction was complete. 4) Repeat Step 2 and 3 for all other amino acids: see below. 5) Coupling for the last position: A solution of 2-bromoacetic acid (4.00 eq) and DIC (4.00 eq) was added to resin and the mixture was bubbled with N2 for 20 min. The coupling reaction was monitored by ninhydrin test, if it showed colorless, the coupling was complete. The resin was then washed with DMF (10 mL) *5, MeOH (10 mL) *5, and then dried under vacuum. Peptide Cleavage and Purification: 1) Add cleavage buffer (2%TFA/2%TIS/96%DCM, 100 mL) to the flask containing the sidechain protected peptide at room temperature with N2 bubbling for 20 min. 2) Filter and collect the filtrate. The clear solution is compound 3 (1.0 mmol) in cleavage buffer (100 mL), and used in next step directly.
  • 13
  • [ 29022-11-5 ]
  • [ 68858-20-8 ]
  • [ 35661-60-0 ]
  • [ 35661-39-3 ]
  • [ 1197020-22-6 ]
  • [ 123622-48-0 ]
  • [ 71989-14-5 ]
  • [ 71989-38-3 ]
  • [ 79-08-3 ]
  • [ 109425-51-6 ]
  • Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
  • [ 199110-64-0 ]
  • fmoc-S-4-methoxytrityl-L-cysteine [ No CAS ]
  • C128H176BrN19O24S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-(9H-fluoren-9-ylmethoxycarbonyl)aminopentanoic acid With N-ethyl-N,N-diisopropylamine In dichloromethane at 15℃; for 2h; Inert atmosphere; Stage #2: With piperidine In N,N-dimethyl-formamide at 15℃; for 0.5h; Inert atmosphere; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; (S)-2-[((9H-Fluoren-9-yl)methoxy)carbonyl]amino}heptanoic acid; Fmoc-(tBu)Asp-OH; Fmoc-Tyr(tBu)-OH; bromoacetic acid; Fmoc-His(Trt)-OH; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; (S)-3-biphenyl-4-yl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid; fmoc-S-4-methoxytrityl-L-cysteine Further stages; 1 Another exemplary Peptide Synthesis. Peptide were synthesized using standard Fmoc chemistry, for example: 1) Resin preparation: To the vessel containing CTC Resin (0.5 mmol, 0.5 g, 1.0 mmol/g) and 5- ((((9H-fluoren-9-yl)methoxy)carbonyl)amino)pentanoic acid (0.17 g, 0.5 mmol, 1.00 eq) in DCM (5 mL) was added DIEA (4.00 eq) dropwise and mix for 2 hr with N2 bubbling at 15 oC. Then added MeOH (0.5 mL) and bubbled with N2 for another 30 min. The resin was washed with DMF (20 mL) *5. Then 20% piperidine in DMF (10 mL) was added and the mixture was bubbled with N2 for 30 mins at 15 °C. Then the mixture was filtered to obtain the resin. The resin was washed with DMF (10 mL) *5 before proceeding to next step. 2) Coupling: A solution of Fmoc-Cys(Mmt)-OH (2.00 eq), HBTU (1.90 eq) in DMF (5 mL) was added to the resin with N2 bubbling. Then DIEA (4.00 eq) was added to the mixture dropwise and bubbled with N2 for 30 min at 15 oC. The coupling reaction was monitored by ninhydrin test, if it showed colorless, the coupling was complete. The resin was then washed with DMF (10 mL) *5. 3) De-protection: 20% piperidine in DMF (10 mL) was added to the resin and the mixture was bubbled with N2 for 30 mins at 15 °C. The resin was then washed with DMF (10 mL) *5. The De- protection reaction was monitored by ninhydrin test, if it showed blue or other brownish red, the reaction was complete. 4) Repeat Step 2 and 3 for all other amino acids: see below. 5) Coupling for the last position: A solution of 2-bromoacetic acid (4.00 eq) and DIC (4.00 eq) was added to resin and the mixture was bubbled with N2 for 20 mins. The coupling reaction was monitored by ninhydrin test, if it showed colorless, the coupling was completed. The resin was then washed with DMF (10 mL) *5, MeOH (10 mL) *5, and then dried under vacuum. Peptide Cleavage and Purification: 3) Add cleavage buffer (2%TFA/2%Tis/96%DCM, 50 mL) to the flask containing the side chain protected peptide at room temperature with N2 bubbling for 20 mins. 4) Filter and collect the filtrate. The clear solution is compound 3 (0.5 mmol) in cleavage buffer (50 mL), and is used in next step directly.
  • 14
  • 5,8,11,14,17,20,23,26-octaoxa-2-azanonacosanedioic acid, 1-(9H-fluoren-9-ylmethyl) ester [ No CAS ]
  • [ 29022-11-5 ]
  • [ 68858-20-8 ]
  • [ 35661-60-0 ]
  • [ 35661-39-3 ]
  • [ 1197020-22-6 ]
  • [ 71989-14-5 ]
  • [ 71989-38-3 ]
  • [ 79-08-3 ]
  • [ 109425-51-6 ]
  • Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
  • [ 199110-64-0 ]
  • fmoc-S-4-methoxytrityl-L-cysteine [ No CAS ]
  • C142H204BrN19O32S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5,8,11,14,17,20,23,26-octaoxa-2-azanonacosanedioic acid, 1-(9H-fluoren-9-ylmethyl) ester With N-ethyl-N,N-diisopropylamine In dichloromethane at 15℃; for 2h; Inert atmosphere; Stage #2: With piperidine In N,N-dimethyl-formamide at 15℃; for 0.5h; Inert atmosphere; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; (S)-2-[((9H-Fluoren-9-yl)methoxy)carbonyl]amino}heptanoic acid; Fmoc-(tBu)Asp-OH; Fmoc-Tyr(tBu)-OH; bromoacetic acid; Fmoc-His(Trt)-OH; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; (S)-3-biphenyl-4-yl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid; fmoc-S-4-methoxytrityl-L-cysteine Further stages; 1 Peptide were synthesized using standard Fmoc chemistry, for example: 1) Resin preparation: To the vessel containing CTC Resin (0.62 mmol, 0.62 g, 1.0 mmol/g, 1.25 eq) and Fmoc-PEG8-CH2CH2COOH (0.198 g, 0.50 mmol, 1.00 eq) in DCM (10 mL) was added DIEA (4.00 eq) dropwise and mix for 2 hrs with N2 bubbling at 15 oC. Then added MeOH (1.0 mL) and bubbled with N2 for another 30 min. The resin was washed with DMF (10 mL) *5. Then 20% piperidine in DMF (10 mL) was added and the mixture was bubbled with N2 for 30 min at 15 °C. Then the mixture was filtered to obtain the resin. The resin was washed with DMF (10 mL) *5 before proceeding to next step. 2) Coupling: A solution of Fmoc-Cys(Mmt)-OH (615 mg, 1.00 mmol, 2.00 eq), HBTU (360 mg, 0.95 mmol, 1.90 eq) in DMF (10 mL) was added to the resin with N2 bubbling. Then DIEA (4.00 eq) was added to the mixture dropwise and bubbled with N2 for 30 min at 15 oC. The coupling reaction was monitored by ninhydrin test, if it showed colorless, the coupling was complete. If it showed blue or brownish red, the coupling was repeated and checked with ninhydrin test again till reaching completion. The resin was then washed with DMF (20 mL) *5. 3) De-protection: 20% piperidine in DMF (20 mL) was added to the resin and the mixture was bubbled with N2 for 30 min at 15 °C. The resin was then washed with DMF (20 mL) *5. The De- protection reaction was monitored by ninhydrin test, if it showed blue or other brownish red, the reaction was complete. 4) Repeat Step 2 and 3 for all other amino acids: see below. 5) Coupling for the last position: A solution of 2-bromoacetic acid (4.00 eq) and DIC (4.00 eq) was added to resin and the mixture was bubbled with N2 for 20 min. The coupling reaction was monitored by ninhydrin test, if it showed colorless, the coupling was completed. The resin was then washed with DMF (20 mL) *5, MeOH (20 mL) *5, and then dried under vacuum. Peptide Cleavage and Purification: 1) Add cleavage buffer (2%TFA/2%TIS/96%DCM, 100 mL) to the flask containing the side chain protected peptide at room temperature with N2 bubbling for 20 min. 2) Filter and collect the filtrate. The clear solution is compound 3 (1.0 mmol, 100 mL) in cleavage buffer, and is used in next step directly.
  • 15
  • [ 29022-11-5 ]
  • [ 68858-20-8 ]
  • [ 35661-60-0 ]
  • [ 35661-39-3 ]
  • [ 1197020-22-6 ]
  • [ 71989-14-5 ]
  • [ 71989-38-3 ]
  • [ 79-08-3 ]
  • [ 109425-51-6 ]
  • Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
  • [ 199110-64-0 ]
  • fmoc-S-4-methoxytrityl-L-cysteine [ No CAS ]
  • C125H170BrN19O24S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-(fluoren-9-ylmethoxycarbonyl)glycine With N-ethyl-N,N-diisopropylamine In dichloromethane at 15℃; for 2h; Inert atmosphere; Stage #2: With piperidine In N,N-dimethyl-formamide at 15℃; for 0.5h; Inert atmosphere; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; (S)-2-[((9H-Fluoren-9-yl)methoxy)carbonyl]amino}heptanoic acid; Fmoc-(tBu)Asp-OH; Fmoc-Tyr(tBu)-OH; bromoacetic acid; Fmoc-His(Trt)-OH; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; (S)-3-biphenyl-4-yl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid; fmoc-S-4-methoxytrityl-L-cysteine Further stages; 1 Another exemplary Peptide Synthesis. Peptide were synthesized using standard Fmoc chemistry, for example: 1) Resin preparation: To the vessel containing CTC Resin (0.5 mmol, 0.50 g, 1.0 mmol/g) and Fmoc-Gly-OH (0.149 g, 0.50 mmol, 1.00 eq) in DCM (5 mL) was added DIEA (4.00 eq) dropwise and mix for 2 hr with N2 bubbling at 15 oC. Then added MeOH (0.5 mL) and bubbled with N2 for another 30 min. The resin was washed with DMF (10 mL) *5, and then 20% piperidine in DMF (10 mL) was added and the mixture was bubbled with N2 for 30 mins at 15 °C. Then the mixture was filtered to obtain the resin. The resin was washed with DMF (10 mL) *5 before proceeding to next step. 2) Coupling: A solution of Fmoc-Cys(Mmt)-OH (2.00 eq), HBTU (1.90 eq) in DMF (5 mL) was added to the resin with N2 bubbling. Then DIEA (4.00 eq) was added to the mixture dropwise and bubbled with N2 for 30 min at 15 oC. The coupling reaction was monitored by ninhydrin test, if it showed colorless, the coupling was complete. If it showed blue or brownish red, the coupling was repeated one more time and checked with ninhydrin test again till coupling reaches completion. The resin was then washed with DMF (10 mL) *5. 3) De-protection: 20% piperidine in DMF (10 mL) was added to the resin and the mixture was bubbled with N2 for 30 min at 15 °C. The resin was then washed with DMF (10 mL) *5. The De- protection reaction was monitored by ninhydrin test, if it showed blue or other brownish red, the reaction was complete. 4) Repeat Step 2 and 3 for all other amino acids: (2-14 in Table 2). 5) Coupling for the last position: A solution of 2-bromoacetic acid (4.00 eq) and DIC (4.00 eq) was added to resin and the mixture was bubbled with N2 for 20 mins. The coupling reaction was monitored by ninhydrin test, if it showed colorless, the coupling was completed. The resin was then washed with DMF (10 mL) *5, MeOH (10 mL) *5, and then dried under vacuum. Peptide Cleavage and Purification: 1) Add cleavage buffer (2%TFA/2%TIS/96%DCM, 100 mL) to the flask containing the sidechain protected peptide at room temperature with N2 bubbling for 20 mins. 2) Filter and collect the filtrate. The clear solution is compound 3 (0.5 mmol, 100 mL) in cleavage buffer, and is used in next step directly. 3) Compound 3 (0.5 mmol, 100 mL, in cleavage buffer) was diluted with MeOH (500 mL), based with TEA to pH = 8 under N2 atmosphere, and then stirred at 15 oC for 4 hr. The solvent was removed under reduced pressure, and the residue was triturated in 0.1 M HCl (cold, 100 mL). After filtration, the solid was washed with H2O (50 mL) and then stirred in isopropyl ether (50 mL) for 10 mins, and finally dried under reduced pressure to get compound 4 (1.2 g, crude).
  • 16
  • [ 29022-11-5 ]
  • [ 68858-20-8 ]
  • [ 35661-60-0 ]
  • [ 35661-39-3 ]
  • [ 1197020-22-6 ]
  • [ 71989-14-5 ]
  • C28H35N5O8S [ No CAS ]
  • [ 71989-38-3 ]
  • [ 109425-51-6 ]
  • Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
  • [ 199110-64-0 ]
  • C131H184N22O26S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: Fmoc-(tBu)Asp-OH With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h; Inert atmosphere; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.5h; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; (S)-2-[((9H-Fluoren-9-yl)methoxy)carbonyl]amino}heptanoic acid; Fmoc-(tBu)Asp-OH; C28H35N5O8S; Fmoc-Tyr(tBu)-OH; Fmoc-His(Trt)-OH; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; (S)-3-biphenyl-4-yl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid Further stages; 1 Exemplary Peptide Synthesis. Peptide were synthesized using standard Fmoc chemistry, for example: 1) Add DCM (10.0 mL) to the vessel containing CTC Resin (2.0 mmol, 2.0 g, 1.0 mmol/g) and Fmoc- Asp(OtBu)-OH (658 mg, 1.60 mmol, 0.80 eq) with N2 bubbling. 2) Add DIEA (4.00 eq) dropwise and mix for 2 hr. 3) Add MeOH (2.0 mL) and mix for 30 min. 4) Drain and wash with DMF for 5 times. 5) Add 20% piperidine/DMF and react for 30 min. 6) Drain and wash with DMF for 5 times. 7) Add Fmoc-amino acid solution and mix for 30 sec first, then add activation buffer, and the coupling reaction lasts for 1 hr with continuous N2 bubbling. 8) Repeat step 4 to 7 for next amino acid coupling. Synthesis scale: 1.6 mmol 20% piperidine in DMF was used for Fmoc deprotection for 30 min. The coupling reaction was monitored by ninhydrin test. After coupling, the Fmoc group was removed, and the resin was washed with MeOH for 3 times, and then dried under vacuum. Peptide Cleavage and Purification: Add cleavage solution (20% HFIP/DCM, 80 mL) to the flask containing the side chain protected peptide at room temperature. The cleavage was carried out twice (30 min each), with continuous N2 bubbling. After filtered, the filtrate was concentrated under reduced pressure and the residue was dried in lyophilizer to give compound 4 (2.9 g, crude) as a white solid. A solution of compound 4 (2.9 g, 1.0 eq), HOBt (308 mg, 2.0 eq), TBTU (732 mg, 2.0 eq), DIEA (0.85 mL, 4.0 eq) in DMF (800 mL) was stirred at 15°C for 1 hr. When cyclization was complete, the solution was then diluted with EA (1.5 L), washed with 1 M HCl (600 mL), brine (400 mL x 4), dried over anhydrous Na2SO4, concentrated under reduced pressure to get compound 5 (3.2 g, crude) as colorless oil. Deprotection of crude cyclic peptide was carried out by treating compound 5 (3.2 g, crude) with TFA/TIS/H2O (95/2.5/2.5, 40 mL in total) by continuous stirring for 1.5 hr at 15°C. The solution was triturated with cold isopropyl ether (500 mL) and the precipitate was collected by centrifugation (3 min at 3000 rpm). The precipitate (deprotected peptide) was washed twice with isopropyl ether (50 mL each), following by drying under vacuum for 2 hr. The residue was purified by prep-HPLC (acidic condition, TFA) to give the compound 6 (600 mg).
  • 17
  • [ 29022-11-5 ]
  • [ 68858-20-8 ]
  • [ 35661-60-0 ]
  • [ 35661-39-3 ]
  • [ 1197020-22-6 ]
  • [ 71989-14-5 ]
  • C39H57N3O13S [ No CAS ]
  • [ 71989-38-3 ]
  • [ 109425-51-6 ]
  • [ 135112-27-5 ]
  • Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
  • [ 199110-64-0 ]
  • C138H200N20O29S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)butanoic acid With N-ethyl-N,N-diisopropylamine In dichloromethane for 2h; Inert atmosphere; Stage #2: With piperidine In N,N-dimethyl-formamide for 0.5h; Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Val-OH; Fmoc-Leu-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine; (S)-2-[((9H-Fluoren-9-yl)methoxy)carbonyl]amino}heptanoic acid; Fmoc-(tBu)Asp-OH; C39H57N3O13S; Fmoc-Tyr(tBu)-OH; Fmoc-His(Trt)-OH; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; (S)-3-biphenyl-4-yl-2-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid Further stages; 1 Another example: 1) Add DCM to the vessel containing CTC Resin (0.500 mmol, 500 mg, 1.00 mmol/g) and Fmoc- Thr(tBu)-OH (130 mg, 0.40 mmol, 0.80 eq) with N2 bubbling. 2) Add DIEA (4.00 eq) dropwise and mix for 2 hours. 3) Add MeOH (0.50 mL) and mix for 30 min. 4) Drain and wash with DMF for 5 times. 5) Add 20% piperidine/DMF and react for 30 min. 6) Drain and wash with DMF for 5 times. 7) Add Fmoc-amino acid solution and mix for 30 sec first, then add activation solution, and the coupling reaction lasts for 1 hr with continuous N2 bubbling. 8) Repeat step 4 to 7 for next amino acid coupling. Synthesis scale: 0.4 mmol. 20% piperidine in DMF was used for Fmoc deprotection for 30 min. The coupling reaction was monitored by ninhydrin test. After last coupling, the resin was washed with MeOH for 3 times, and then dried under vacuum. Peptide Cleavage and Purification: Add cleavage solution (20% HFIP/DCM, 20 mL) to the flask containing the side chain protected peptide at room temperature. The cleavage was carried out twice (30 min each), with continuous N2 bubbling. After filtered, the filtrate was concentrated under reduced pressure and the residue was dried in lyophilizer to give compound 6 (1.0 g, crude) as a white solid.
  • 18
  • [ 35661-60-0 ]
  • [ 1197020-22-6 ]
  • (2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(2-tert-butoxy-2-oxoethoxy)pyrrolidine-2-carboxylic acid [ No CAS ]
  • [ 71989-33-8 ]
  • [ 71989-14-5 ]
  • [ 108-24-7 ]
  • [ 71989-23-6 ]
  • [ 71989-38-3 ]
  • [ 103213-32-7 ]
  • fmoc-L-Arg(Pbf)-OH [ No CAS ]
  • [ 199110-64-0 ]
  • C94H146N28O23S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: fmoc-L-Arg(Pbf)-OH With ethyl (hydroxyimino)cyanoacetate; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 90℃; Microwave irradiation; Automated synthesizer; Stage #2: With piperidine In N,N-dimethyl-formamide Stage #3: Fmoc-Leu-OH; (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)heptanoic acid; (2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(2-tert-butoxy-2-oxoethoxy)pyrrolidine-2-carboxylic acid; Fmoc-Ser(tBu)-OH; Fmoc-(tBu)Asp-OH; acetic anhydride; Fmoc-Ile-OH; Fmoc-Tyr(tBu)-OH; N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine; fmoc-L-Arg(Pbf)-OH; (S)-2((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-([1,1'-biphenyl]-4-yl)propanoic acid Further stages;
  • 19
  • [ 35661-60-0 ]
  • [ 1197020-22-6 ]
  • [ 71989-31-6 ]
  • [ 71989-33-8 ]
  • [ 71989-14-5 ]
  • [ 108-24-7 ]
  • C23H23NO5 [ No CAS ]
  • [ 71989-23-6 ]
  • [ 71989-38-3 ]
  • [ 103213-32-7 ]
  • Fmoc-S-trityl-D-cysteine [ No CAS ]
  • fmoc-L-Arg(Pbf)-OH [ No CAS ]
  • [ 199110-64-0 ]
  • C95H148N28O21S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: fmoc-L-Arg(Pbf)-OH With ethyl (hydroxyimino)cyanoacetate; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 90℃; Microwave irradiation; Automated synthesizer; Stage #2: With piperidine In N,N-dimethyl-formamide Stage #3: Fmoc-Leu-OH; (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)heptanoic acid; Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; Fmoc-(tBu)Asp-OH; acetic anhydride; C23H23NO5; Fmoc-Ile-OH; Fmoc-Tyr(tBu)-OH; N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine; Fmoc-S-trityl-D-cysteine; fmoc-L-Arg(Pbf)-OH; (S)-2((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-([1,1'-biphenyl]-4-yl)propanoic acid Further stages;
  • 20
  • [ 35661-60-0 ]
  • [ 281655-32-1 ]
  • [ 1197020-22-6 ]
  • [ 71989-31-6 ]
  • [ 71989-33-8 ]
  • [ 71989-14-5 ]
  • [ 108-24-7 ]
  • [ 71989-23-6 ]
  • [ 71989-38-3 ]
  • [ 103213-32-7 ]
  • Fmoc-S-trityl-D-cysteine [ No CAS ]
  • fmoc-L-Arg(Pbf)-OH [ No CAS ]
  • [ 199110-64-0 ]
  • C98H148N28O20S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: fmoc-L-Arg(Pbf)-OH With ethyl (hydroxyimino)cyanoacetate; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 90℃; Microwave irradiation; Automated synthesizer; Stage #2: With piperidine In N,N-dimethyl-formamide Stage #3: Fmoc-Leu-OH; (2S,3R)-3-phenyl-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester; (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)heptanoic acid; Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; Fmoc-(tBu)Asp-OH; acetic anhydride; Fmoc-Ile-OH; Fmoc-Tyr(tBu)-OH; N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine; Fmoc-S-trityl-D-cysteine; fmoc-L-Arg(Pbf)-OH; (S)-2((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-([1,1'-biphenyl]-4-yl)propanoic acid Further stages;
  • 21
  • [ 35661-60-0 ]
  • [ 1197020-22-6 ]
  • [ 71989-31-6 ]
  • [ 71989-33-8 ]
  • [ 71989-14-5 ]
  • [ 108-24-7 ]
  • [ 71989-23-6 ]
  • [ 71989-38-3 ]
  • [ 103213-32-7 ]
  • fmoc-L-Arg(Pbf)-OH [ No CAS ]
  • [ 199110-64-0 ]
  • C92H144N28O20S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: fmoc-L-Arg(Pbf)-OH With ethyl (hydroxyimino)cyanoacetate; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 90℃; Microwave irradiation; Automated synthesizer; Stage #2: With piperidine In N,N-dimethyl-formamide Stage #3: Fmoc-Leu-OH; (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)heptanoic acid; Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; Fmoc-(tBu)Asp-OH; acetic anhydride; Fmoc-Ile-OH; Fmoc-Tyr(tBu)-OH; N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine; fmoc-L-Arg(Pbf)-OH; (S)-2((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-([1,1'-biphenyl]-4-yl)propanoic acid Further stages;
Same Skeleton Products
Historical Records