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[ CAS No. 99953-00-1 ] {[proInfo.proName]}

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Chemical Structure| 99953-00-1
Chemical Structure| 99953-00-1
Structure of 99953-00-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 99953-00-1 ]

CAS No. :99953-00-1 MDL No. :MFCD01860643
Formula : C16H23NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :QSKQZXRPUXGSLR-ZDUSSCGKSA-N
M.W : 309.36 Pubchem ID :13656657
Synonyms :

Safety of [ 99953-00-1 ]

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 [ 99953-00-1 ]

* 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 [ 99953-00-1 ]

[ 99953-00-1 ] Synthesis Path-Downstream   1~27

  • 2
  • [ 42429-27-6 ]
  • [ 99953-00-1 ]
  • [ 579491-20-6 ]
  • 3
  • [ 99953-00-1 ]
  • [ 71989-14-5 ]
  • [ 76-05-1 ]
  • [ 171859-74-8 ]
  • (R)-3-({2-[(S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-succinamic acid; compound with trifluoro-acetic acid [ No CAS ]
  • 4
  • [ 99953-00-1 ]
  • [ 104091-08-9 ]
  • [ 76-05-1 ]
  • [ 171859-74-8 ]
  • (R)-4-({2-[(S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-4-carbamoyl-butyric acid; compound with trifluoro-acetic acid [ No CAS ]
  • 5
  • [ 71989-18-9 ]
  • [ 136030-33-6 ]
  • [ 99953-00-1 ]
  • [ 76-05-1 ]
  • [ 845255-75-6 ]
  • (S)-4-({(S)-2-[(S)-2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinoline-3-carbonyl}-amino)-4-[(S)-1-carbamoyl-2-(6-dimethylamino-1,3-dioxo-1,3-dihydro-benzo[f]isoindol-2-yl)-ethylcarbamoyl]-butyric acid; compound with trifluoro-acetic acid [ No CAS ]
  • 6
  • [ 71989-18-9 ]
  • [ 136030-33-6 ]
  • [ 99953-00-1 ]
  • [ 88574-06-5 ]
  • [ 76-05-1 ]
  • Fmoc-α-amino-β-(6-N,N-dimethylamino naphthalimide)propanoic acid [ No CAS ]
  • C49H58N8O10*2C2HF3O2 [ No CAS ]
  • 7
  • [ 69630-60-0 ]
  • [ 99953-00-1 ]
  • [ 543-27-1 ]
  • [ 80102-93-8 ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; acetic acid In <i>N</i>-methyl-acetamide; methanol; chloroform; water 35 EXAMPLE 35 EXAMPLE 35 A solution of 5.34 g of Boc-DL-2,6-dimethyltyrosine and 2.0 ml of N-methylmorpholine is cooled to -20° C. The temperature is maintained at -17° C. to -20° C. while 2.4 ml of isobutylchloroformate are added dropwise. The reaction mixture is stirred for 5 minutes then a solution of 2.1 ml of N-methylmorpholine and 3.63 g of methyl D-methioninate hydrochloride in 10 ml of dimethylformamide is added while maintaining the temperature at about -20° C. The reaction mixture is stirred for 30 minutes at -20° C. then warmed to room temperature and allowed to stand overnight. The reaction mixture is added to 600 ml of a cold, 5% solution of potassium bisulfate. The gummy precipitate which forms is filtered, washed four times with 100 ml of cold water and dried under reduced pressure. Purification by low pressure chromatography on silica gel using chloroform:methanol:acetic acid:water (98:1.8:0.01) as eluent gives methyl Boc-2,6-dimethyl-DL-tyrosyl-D-methioninate.
  • 8
  • [ 264273-08-7 ]
  • [ 99953-00-1 ]
  • N-α-[(9H-fluoren-9-ylmethoxy)carbonyl]-NG-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-D-arginine [ No CAS ]
  • [ 1286708-12-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: C27H24N2O5 With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; solid phase reaction; Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.333333h; solid phase reaction; Stage #3: (S)-N-Boc-2,6-dimethyltyrosine; N-α-[(9H-fluoren-9-ylmethoxy)carbonyl]-NG-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-D-arginine Further stages;
  • 9
  • Boc-Aba-Gly [ No CAS ]
  • [ 13734-31-1 ]
  • [ 99953-00-1 ]
  • [ 1345697-93-9 ]
  • 11
  • [ 57060-88-5 ]
  • [ 99953-00-1 ]
  • Boc-Dmt-Tic-OMe [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 5.0h; To a solution of Boc-Dmt-OH (309 mg, 1 mmol), HBTU (379 mg, 1 mmol) and DIEA (348 muL, 2 mmol) in 5 mL DMF was added a solution of HCl x H-Tic-OMe (227.5 mg, 1 mmol) and DIEA (174 muL, 1 mmol) in 5 mL DMF. The reaction mixture was stirred for 5 h at room temperature and progress of the reaction was monitored by TLC. After solvent evaporation in vacuo, the residue was dissolved in 50 mL AcOEt and the resulting solution was washed with 5% KHSO4 (aq.), saturated NaHCO3 (aq.) and brine. The organic phase was dried (MgSO4), filtered and evaporated to dryness, yielding 430 mg of crude product (90% yield). The crude Boc-protected dipeptide ester was deprotected by treatment with aqueous TFA (95% vv) for 45 min under stirring and cooling with ice. After TFA evaporation in vacuo, the TFA salt of the dipeptide ester was precipitated with ether (Et2O), affording 300 mg (90% yield) of crude product which was purified by preparative HPLC. TFA x H-Dmt-Tic-OMe: TLC Rf (I) 0.55; MS [M+H]+ 383.
  • 12
  • [ 99953-00-1 ]
  • [ 97480-93-8 ]
  • C30H43N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; 6-chloro-1-hydroxybenzotriazole; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate at 20℃; for 15h; General Procedure B for Compounds 3-12 General procedure: (S)-2-amino-1-(4-benzylpiperidin-1-yl)-3-(4-hydroxy-2,6-dimethylphenyl)propan-1-one (3). To a solution of 4-benzylpiperidine (0.100 g, 0.57 mmol), Boc-L-Dmt (0.234 g, 0.57 mmol) and DIEA (1.00 mL, 5.7 mmol) was added HATU (0.217 g, 0.571 mmol) and HOBt-Cl (0.097 g, 0.57 mmol) and allowed to stir at r.t. for 15 h. H2O was then added, and extracted with EtOAc. Combined organic layers were washed with brine and dried with MgSO4. Solvents were filtered and removed, and residue was redissolved in 1:1 DCM/TFA (6 mL) and allowed to stir for 1 h. Solvents were removed, and residue was purified by RP-HPLC to give product as a white solid.
  • 13
  • [ 99953-00-1 ]
  • [ 97480-93-8 ]
  • [ 1535200-73-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; 6-chloro-1-hydroxybenzotriazole / 15 h / 20 °C 2: trifluoroacetic acid / dichloromethane / 1 h
  • 14
  • [ 35899-89-9 ]
  • 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl [ No CAS ]
  • [ 35661-40-6 ]
  • [ 99953-00-1 ]
  • [ 198561-07-8 ]
  • [ 1558028-95-7 ]
  • 15
  • [ 35899-89-9 ]
  • [ 1204595-05-0 ]
  • 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl [ No CAS ]
  • [ 35661-40-6 ]
  • [ 99953-00-1 ]
  • [ 1558028-98-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: (S)-2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-[4-(prop-2-yn-1-yloxy)phenyl]propanoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1.5h; Stage #2: With 4-methylpiperidin In N,N-dimethyl-formamide for 0.333333h; Stage #3: 1-amido-1-deoxygalactopyranose; 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl; N-Fmoc L-Phe; (S)-N-Boc-2,6-dimethyltyrosine Further stages;
  • 16
  • [ 20379-59-3 ]
  • 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl [ No CAS ]
  • [ 35661-40-6 ]
  • [ 99953-00-1 ]
  • [ 198561-07-8 ]
  • [ 1558028-96-8 ]
  • 17
  • 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl [ No CAS ]
  • [ 35661-40-6 ]
  • [ 99953-00-1 ]
  • [ 198561-07-8 ]
  • [ 1558028-91-3 ]
  • 18
  • [ 1204595-05-0 ]
  • 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl [ No CAS ]
  • [ 35661-40-6 ]
  • [ 99953-00-1 ]
  • C38H48N8O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: (S)-2-([(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-[4-(prop-2-yn-1-yloxy)phenyl]propanoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1.5h; Stage #2: With 4-methylpiperidin In N,N-dimethyl-formamide for 0.333333h; Stage #3: 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl; N-Fmoc L-Phe; (S)-N-Boc-2,6-dimethyltyrosine Further stages;
  • 19
  • [ 560088-66-6 ]
  • Wang-Fmoc-Lys(Mtt)-OH resin [ No CAS ]
  • [ 136030-33-6 ]
  • [ 99953-00-1 ]
  • fmoc-S-4-methoxytrityl-L-cysteine [ No CAS ]
  • [ 170908-81-3 ]
  • C49H72N10O16S [ No CAS ]
YieldReaction ConditionsOperation in experiment
This was achieved from Wang resin, which was mesylated using an 8-fold excess of MsCI at 0C to activate OH groups, followed by coupling with Fmoc-Lys(Mtt)-OH. In a 50 mL bottle containing 1 g of Wang resin (0.93 mmol/g) with a magnetic stir bar, dry CH2CI2 was added to swell the resin for 1 h. The solvent was removed, the bottle closed with a septum and flushed with nitrogen, and /'Pr2NEt (9 equiv, 1.4 mL) in 15 mL of CH2CI2 was added. The resin slurry was cooled to 0C followed by dropwise addition of MsCI (8 equiv, 0.57 mL) in 2 mL of CH2CI2. The reaction was stirred for 20 min, the ice-bath was removed, and the stirring was continued for another 20 min (rt). The resin was then transferred to a syringe reactor and washed with dry CH2CI2 and dry DMF. Fmoc-Lys(Mtt)-OH (2 equiv, 1 .2g), Csl (2 equiv, 0.5g), /'Pr2NEt (2 equiv, 0.32 mL) in ca. 10 mL of dry DMF were added, and the reaction was stirred overnight at rt. The NR-Fmoc protection from 3 was removed with piperidine in DMF, and Fmoc- Tic-OH was coupled using standard NR-Fmoc/iBu strategy of solid-phase peptide synthesis to give intermediate 4. The resin was NR-Fmoc deprotected with piperidine/DMF (1 :4) and then washed with DMF, CH2CI2, 0.2 M HOBt/DMF, and DMF. Fmoc-Tic-OH (3 equiv), HOCt (3 equiv), and DIC (6 equiv) in DMF were then added, and the reaction was stirred for 2 h. For final coupling, Boc-Dmt-OH was used since a free N terminal peptide can be directly obtained after final acidic cleavage. Additionally, a choice of NR-terminal Boc protection prevents against premature Fmoc deprotection by free NH2 groups released on the side chain of lysine and any consequent cyclative elimination (dioxopiperazine) of Dmt- Tic from Dmt-Tic- Lys(R)-resin. (Caspasso, S.; Sica, F.; Mazzarella, L.; Balboni, G.; Guerrini, R.; Salvadori, S. Int. J. Pep. Protein Res. 1995, 45, 567-573) Lastly, Boc is smaller than Fmoc, facilitating a faster coupling rate. Despite that, Boc- Dmt coupling to the sterically hindered Tic-Lys(R)-resin was challenging. The coupling has to be mediated via strong HBTU activation accelerated by microwave. Boc-Dmt-OH (3 equiv), HBTU (3 equiv), and /'Pr2NEt (6 equiv) in DMF were added to the resin, and the reaction was heated in a household microwave for 3 s. The reaction was stirred until it cooled to rt; the heating was repeated (5x), and the resin was stirred for another 2 h. Also, there is a conceptual disadvantage of using an unprotected phenolic group on Dmt. The reaction leads to Dmt self-condensation, forming small amounts of Dmt-oligomers. Nonetheless, the formed phenolic esters are susceptible to mild aminolysis and can be selectively removed by treatment with 50% piperidine in CH2CI2:MeOH (5:1 ) before acidic cleavage. Following Dmt coupling to give intermediate 5, the coupling of dyes and chelating agents can be performed on the resin or in solution. For Cy5 labeling, more cost-effective conjugation of dye in solution was preferred via a thiolmaleimide reaction. 3-Mercaptopropionyl was chosen as a small linker for C-terminal attachment as the dye possesses a 12-atom linker with maleimide at the end. Thus, Trt-SCH2CH2COOH was coupled to 5 using HOCt/DIC protocol and then cleaved with acidic cocktail (82.5% TFA, 5% H20, 5% /'Pr3SiH, 5% thioanisole, and 2.5% ethanedithiol) to give ligand 6 (Scheme 2 shown in Figure 17). Following Dmt coupling to give intermediate 5, the coupling of dyes and chelating agents can be performed on the resin or in solution. For Cy5 labeling, more cost-effective conjugation of dye in solution was preferred via a thiolmaleimide reaction. 3-Mercaptopropionyl was chosen as a small linker for C-terminal attachment as the dye possesses a 12-atom linker with maleimide at the end. Thus, Trt-SCH2CH2COOH was coupled to 5 using HOCt/DIC protocol and then cleaved with acidic cocktail (82.5% TFA, 5% H20, 5% /'Pr3SiH, 5% thioanisole, and 2.5% ethanedithiol) to give ligand 6 (Scheme 2 shown in Figure 17). The compound was purified by preparative HPLC, and the Cy5 dye was conjugated to the peptide in solution to give ligand 1. Ligand 8 was dissolved in HEPES buffer (pH 7.2), and 1 .3 equiv of Cy5-maleimide was added in aliquots until full conversion was achieved as monitored on analytical HPLC. The labeled ligand was then separated with SPE.The on-resin labeling was tested by synthesizing a DOTA chelate as shown in Scheme 3 (Figure 18). The Mtt protection on lysine was removed with 3% TFA and 5% /'Pr3SiH in CH2CI2. Here the inventors employed a bifunctional handle to investigate its utility for coupling commonly available labeling moieties, for dual-modality labeling (e.g., optical/magnetic), for coupling to nanoparticles with lanthanide labels, and for preparing dimeric ligands at a later stage (unpublished data). For this purpose, the synthetic scheme was designed to incorporate orthogonally protected Fmoc-Cys(Mmt)-OH at the end of the Ado linker and coupled using standard NR-Fmoc/iBu strategy to give intermediate 7. T...
  • 20
  • Wang-Fmoc-Lys(Mtt)-OH resin [ No CAS ]
  • [ 27144-18-9 ]
  • [ 136030-33-6 ]
  • [ 99953-00-1 ]
  • [ 1160761-39-6 ]
YieldReaction ConditionsOperation in experiment
This was achieved from Wang resin, which was mesylated using an 8-fold excess of MsCI at 0C to activate OH groups, followed by coupling with Fmoc-Lys(Mtt)-OH. In a 50 mL bottle containing 1 g of Wang resin (0.93 mmol/g) with a magnetic stir bar, dry CH2CI2 was added to swell the resin for 1 h. The solvent was removed, the bottle closed with a septum and flushed with nitrogen, and /'Pr2NEt (9 equiv, 1.4 mL) in 15 mL of CH2CI2 was added. The resin slurry was cooled to 0C followed by dropwise addition of MsCI (8 equiv, 0.57 mL) in 2 mL of CH2CI2. The reaction was stirred for 20 min, the ice-bath was removed, and the stirring was continued for another 20 min (rt). The resin was then transferred to a syringe reactor and washed with dry CH2CI2 and dry DMF. Fmoc-Lys(Mtt)-OH (2 equiv, 1 .2g), Csl (2 equiv, 0.5g), /'Pr2NEt (2 equiv, 0.32 mL) in ca. 10 mL of dry DMF were added, and the reaction was stirred overnight at rt. The NR-Fmoc protection from 3 was removed with piperidine in DMF, and Fmoc- Tic-OH was coupled using standard NR-Fmoc/iBu strategy of solid-phase peptide synthesis to give intermediate 4. The resin was NR-Fmoc deprotected with piperidine/DMF (1 :4) and then washed with DMF, CH2CI2, 0.2 M HOBt/DMF, and DMF. Fmoc-Tic-OH (3 equiv), HOCt (3 equiv), and DIC (6 equiv) in DMF were then added, and the reaction was stirred for 2 h. For final coupling, Boc-Dmt-OH was used since a free N terminal peptide can be directly obtained after final acidic cleavage. Additionally, a choice of NR-terminal Boc protection prevents against premature Fmoc deprotection by free NH2 groups released on the side chain of lysine and any consequent cyclative elimination (dioxopiperazine) of Dmt- Tic from Dmt-Tic- Lys(R)-resin. (Caspasso, S.; Sica, F.; Mazzarella, L.; Balboni, G.; Guerrini, R.; Salvadori, S. Int. J. Pep. Protein Res. 1995, 45, 567-573) Lastly, Boc is smaller than Fmoc, facilitating a faster coupling rate. Despite that, Boc- Dmt coupling to the sterically hindered Tic-Lys(R)-resin was challenging. The coupling has to be mediated via strong HBTU activation accelerated by microwave. Boc-Dmt-OH (3 equiv), HBTU (3 equiv), and /'Pr2NEt (6 equiv) in DMF were added to the resin, and the reaction was heated in a household microwave for 3 s. The reaction was stirred until it cooled to rt; the heating was repeated (5x), and the resin was stirred for another 2 h. Also, there is a conceptual disadvantage of using an unprotected phenolic group on Dmt. The reaction leads to Dmt self-condensation, forming small amounts of Dmt-oligomers. Nonetheless, the formed phenolic esters are susceptible to mild aminolysis and can be selectively removed by treatment with 50% piperidine in CH2CI2:MeOH (5:1 ) before acidic cleavage. Following Dmt coupling to give intermediate 5, the coupling of dyes and chelating agents can be performed on the resin or in solution. For Cy5 labeling, more cost-effective conjugation of dye in solution was preferred via a thiolmaleimide reaction. 3-Mercaptopropionyl was chosen as a small linker for C-terminal attachment as the dye possesses a 12-atom linker with maleimide at the end. Thus, Trt-SCH2CH2COOH was coupled to 5 using HOCt/DIC protocol and then cleaved with acidic cocktail (82.5% TFA, 5% H20, 5% /'Pr3SiH, 5% thioanisole, and 2.5% ethanedithiol) to give ligand 6 (Scheme 2 shown in Figure 17).
  • 21
  • [ 200344-33-8 ]
  • C13H15N2O2Pol [ No CAS ]
  • [ 99953-00-1 ]
  • C35H48N6O9 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: All peptides were synthesized manually by Fmoc-based solid phase peptide synthesis (SPPS) on 2-chlorotritylchloride resin (0.15 mmol scale). The first amino acid (Fmoc-Gly-OH or Fmoc-beta-Ala-OH) was loaded onto the resin by use of 2 eq. Fmoc-protected amino acid with 4 eq. DIPEA in CH2Cl2 for 2 h. The remaining chlorines were substituted by treatment of the resin with a mixture of MeOH/CH2Cl2/DIPEA (2:17:1) during 4 times 5 min. For normal couplings, a 3-fold excess of the Fmoc-protected amino acids (Fmoc-D-Arg(Pbf)-OH, <strong>[200344-33-8]Fmoc-D-Cit-OH</strong>) and 3-fold excess of coupling reagent (TBTU) in 0.4 NMM in DMF was used for 1.5 h. Fmoc deprotection was carried out by treatment of the resin with 20% 4-methylpiperidine in DMF for 5 and 15 min. After every reaction step, the resin was washed with DMF (3× 1 min), iPrOH (3× 1 min) and CH2Cl2 (3× 1 min). The reductive amination was executed after Fmoc deprotection of the first amino acid. The resin was first swollen in 0.5% AcOH in TMOF/CH2Cl2 for 30 min and filtered. Two equivalents of Phth-ortho-formyl phenylalanine [32] were dissolved in the same mixture and 4 eq. of NaBH3CN was dissolved in a minimum volume of DMF. Both solutions were added to the resin and the reaction vessel was shaken for 30 min. The course of the reaction was monitored after this time by the Kaiser test. When the test was positive, the reaction was left for another 30 min. The monitoring is repeated until the reaction remains complete, which is indicated by a light red colour of the Kaiser test due to the presence of the secondary amine.
  • 22
  • [ 99953-00-1 ]
  • [ 123715-02-6 ]
YieldReaction ConditionsOperation in experiment
83% With hydrogenchloride; In water; 4.0 g of (S) -O-benzyl-N- (tert-butoxycarbonyl) -2,6-dimethyl-tyrosine prepared in Step 3 was dissolved in 40 ml of methanol, 0.5 g of 10% Pd- The benzyl protecting group is removed through a hydrogen reaction at a hydrogen pressure of 40 psi for 24 hours. After completion of the reaction, the Pd-C catalyst was removed by filtration, 20 ml of 6N hydrochloric acid was added to the filtrate, and the amine protecting group Boc was deprotected All. After completion of the reaction, the reaction mixture was concentrated under reduced pressure to remove methanol. The pH of the reaction mixture was adjusted to 6.0 ± 0.5 with 1 N NaOH solution. The resulting solid was filtered and dried to obtain 1.73 g of the target compound (yield: 83%).
  • 23
  • [ 29022-11-5 ]
  • [ 82565-68-2 ]
  • [ 99953-00-1 ]
  • Fmoc-D-arginine [ No CAS ]
  • C33H46IN8O7Pol [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: Peptide amides were synthesized on Rink Amide resin following Fmoc-based solid-phase peptide synthesis (SPPS) standard protocols in a polypropylene syringe with polyethylene frit using SPPS grade CH2Cl2 or DMF. Fmoc-protected amino acids (3 eq) were mixed with HBTU (3 eq) and DIPEA (3 eq) in DMF and added to the swollen resin beads. The mixture was shaken for 120 mins and washed with DMF (3x), iPrOH (3x) and DCM (3x). Complete coupling was checked by Kaiser ninhydrine test. If complete, the Fmoc protecting group was removed by treatment with 20% 4-methylpiperidine in DMF for 5 min, followed by 15 min and washed. The final amino acid, Boc-Dmt-OH (2 eq) was coupled with DIC (2 eq) and HOBt (2 eq). After assembling of the peptide on solid phase, the peptide was submitted to solid-phase Suzuki-Miyaura derivatization for the (hetero)aryl substituted tetrapeptides. For vinylated peptides, it was found that acidic cleavage of vinylated peptides on resin afforded several unwanted side products. This could be avoided by first performing the peptide cleavage and next a solution-phase Suzuki-Miyaura coupling. This strategy was chosen for the assembly of vinylated tetrapeptides.
  • 24
  • [ 29022-11-5 ]
  • [ 82565-68-2 ]
  • [ 99953-00-1 ]
  • Fmoc-D-arginine [ No CAS ]
  • C28H39IN8O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: Peptide amides were synthesized on Rink Amide resin following Fmoc-based solid-phase peptide synthesis (SPPS) standard protocols in a polypropylene syringe with polyethylene frit using SPPS grade CH2Cl2 or DMF. Fmoc-protected amino acids (3 eq) were mixed with HBTU (3 eq) and DIPEA (3 eq) in DMF and added to the swollen resin beads. The mixture was shaken for 120 mins and washed with DMF (3x), iPrOH (3x) and DCM (3x). Complete coupling was checked by Kaiser ninhydrine test. If complete, the Fmoc protecting group was removed by treatment with 20% 4-methylpiperidine in DMF for 5 min, followed by 15 min and washed. The final amino acid, Boc-Dmt-OH (2 eq) was coupled with DIC (2 eq) and HOBt (2 eq). After assembling of the peptide on solid phase, the peptide was submitted to solid-phase Suzuki-Miyaura derivatization for the (hetero)aryl substituted tetrapeptides. For vinylated peptides, it was found that acidic cleavage of vinylated peptides on resin afforded several unwanted side products. This could be avoided by first performing the peptide cleavage and next a solution-phase Suzuki-Miyaura coupling. This strategy was chosen for the assembly of vinylated tetrapeptides.
  • 25
  • [ 29022-11-5 ]
  • [ 99953-00-1 ]
  • Fmoc-D-arginine [ No CAS ]
  • [ 210282-31-8 ]
  • C33H46IN8O7Pol [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: Peptide amides were synthesized on Rink Amide resin following Fmoc-based solid-phase peptide synthesis (SPPS) standard protocols in a polypropylene syringe with polyethylene frit using SPPS grade CH2Cl2 or DMF. Fmoc-protected amino acids (3 eq) were mixed with HBTU (3 eq) and DIPEA (3 eq) in DMF and added to the swollen resin beads. The mixture was shaken for 120 mins and washed with DMF (3x), iPrOH (3x) and DCM (3x). Complete coupling was checked by Kaiser ninhydrine test. If complete, the Fmoc protecting group was removed by treatment with 20% 4-methylpiperidine in DMF for 5 min, followed by 15 min and washed. The final amino acid, Boc-Dmt-OH (2 eq) was coupled with DIC (2 eq) and HOBt (2 eq). After assembling of the peptide on solid phase, the peptide was submitted to solid-phase Suzuki-Miyaura derivatization for the (hetero)aryl substituted tetrapeptides. For vinylated peptides, it was found that acidic cleavage of vinylated peptides on resin afforded several unwanted side products. This could be avoided by first performing the peptide cleavage and next a solution-phase Suzuki-Miyaura coupling. This strategy was chosen for the assembly of vinylated tetrapeptides.
  • 26
  • [ 29022-11-5 ]
  • [ 99953-00-1 ]
  • Fmoc-D-arginine [ No CAS ]
  • [ 210282-31-8 ]
  • C28H39IN8O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: Peptide amides were synthesized on Rink Amide resin following Fmoc-based solid-phase peptide synthesis (SPPS) standard protocols in a polypropylene syringe with polyethylene frit using SPPS grade CH2Cl2 or DMF. Fmoc-protected amino acids (3 eq) were mixed with HBTU (3 eq) and DIPEA (3 eq) in DMF and added to the swollen resin beads. The mixture was shaken for 120 mins and washed with DMF (3x), iPrOH (3x) and DCM (3x). Complete coupling was checked by Kaiser ninhydrine test. If complete, the Fmoc protecting group was removed by treatment with 20% 4-methylpiperidine in DMF for 5 min, followed by 15 min and washed. The final amino acid, Boc-Dmt-OH (2 eq) was coupled with DIC (2 eq) and HOBt (2 eq). After assembling of the peptide on solid phase, the peptide was submitted to solid-phase Suzuki-Miyaura derivatization for the (hetero)aryl substituted tetrapeptides. For vinylated peptides, it was found that acidic cleavage of vinylated peptides on resin afforded several unwanted side products. This could be avoided by first performing the peptide cleavage and next a solution-phase Suzuki-Miyaura coupling. This strategy was chosen for the assembly of vinylated tetrapeptides.
  • 27
  • [ 68858-20-8 ]
  • [ 86123-10-6 ]
  • [ 99953-00-1 ]
  • [ 84624-17-9 ]
  • [ 169275-84-7 ]
  • C59H82N6O24 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Peptide assembly was performed using Fmoc chemistry on 0.5 mmol scale on Fmoc- Rink-amide polystyrene resin (substitution value 0.67 mmol/g). Fmoc deprotections were accomplished by treatments with 50% piperidine / DMF (2 x 1 min). Couplings were performed using three equivalents of Fmoc amino acid / HBTU / DIEA (1 :1 :1) relative to resin loading (30 min). A/a-Fmoc-0-p-lactosyl-L-serine was incorporated as the hepta-O-acetate (prepared as described above); A/a-Boc-2,6-dimethyl-L-tyrosine was used without side-chain protection. Cleavage from the resin and removal of side-chain protecting groups was achieved by treatment with 95% TFA / 2.5% TIPS / 2.5% H2O for 2 h at room temperature. TFA was removed under a stream of nitrogen, and the product was precipitated using cold diethyl ether / n-hexane (1 :1), washed with Et20, redissolved in 50% acetonitrile / 0.1% TFA / H2O and lyophilised. ESI-MS (m/z) calc. 1259.5 [M+H]+, found 1259.7.
Same Skeleton Products
Historical Records