Home Cart Sign in  
Chemical Structure| 203866-20-0 Chemical Structure| 203866-20-0

Structure of Fmoc-trans-4-F-Pro-OH
CAS No.: 203866-20-0

Chemical Structure| 203866-20-0

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 203866-20-0 ]

CAS No. :203866-20-0
Formula : C20H18FNO4
M.W : 355.36
SMILES Code : O=C(O)[C@H]1N(C(OCC2C3=CC=CC=C3C4=CC=CC=C24)=O)C[C@H](F)C1
MDL No. :MFCD03424224
InChI Key :CJEQUGHYFSTTQT-XIKOKIGWSA-N
Pubchem ID :10970300

Safety of [ 203866-20-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 203866-20-0 ]

* 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 [ 203866-20-0 ]

[ 203866-20-0 ] Synthesis Path-Downstream   1~2

  • 1
  • Fmoc-N-methyl norleucine [ No CAS ]
  • [ 29022-11-5 ]
  • [ 71989-31-6 ]
  • [ 71989-18-9 ]
  • [ 71989-38-3 ]
  • [ 103213-32-7 ]
  • [ 84000-07-7 ]
  • [ 132388-59-1 ]
  • [ 109425-51-6 ]
  • [ 79-11-8 ]
  • [ 125238-99-5 ]
  • [ 143824-78-6 ]
  • [ 203866-20-0 ]
  • C89H123ClFN23O20S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Single-Coupling Procedure To the reaction vessel containing resin from the previous step was added piperidine:DMF (20:80 v/v, 2.0mL). The mixture was periodically agitated for 3 minutes and then the solution was drained through the frit.To the reaction vessel was added piperidine:DMF (20:80 v/v, 2.0 mL). The mixture was periodically agitatedfor 3 minutes and then the solution was drained through the frit. The resin washed successively six times asfollows: for each wash, DMF (2.0 mL) was added to top of the vessel (not through the bottom frit) and theresulting mixture was periodically agitated for 30 seconds before the solution was drained through the frit. Tothe reaction vessel was added the amino acid (0.2M in DMF, 1.0 mL, 2 eq), then HATU (0.2M in DMF, 1.0mL, 2 eq), and finally DIPEA (0.4M in DMF, 1.0 mL, 4 eq). The mixture was periodically agitated for 15minutes, then the reaction solution was drained through the frit. The resin washed successively four times asfollows: for each wash, DMF (2.0 mL) was added to top of the vessel (not through the bottom frit) and theresulting mixture was periodically agitated for 30 seconds before the solution was drained through the frit. Tothe reaction vessel was added acetic anhydride (2.0 mL). The mixture was periodically agitated for 10minutes, then the solution was drained through the frit. The resin washed successively four times as follows:for each wash, DMF (2.0 mL) was added to top of the vessel (not through the bottom frit) and the resultingmixture was periodically agitated for 90 seconds before the solution was drained through the frit. Theresulting resin was used directly in the next step.
  • 2
  • [ 65-85-0 ]
  • [ 138775-22-1 ]
  • [ 142-62-1 ]
  • [ 203866-20-0 ]
  • [ 204316-32-5 ]
  • (2S,4R)-N-[(1S)-1-[[(1S)-3-benzamido-1-(hydroxycarbamoyl)propyl]carbamoyl]-2-methylbutyl]-4-fluoro-N-methyl-1-hexanoyl-pyrrolidine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.5 eq of commercially available Fmoc-NH-OH and DIEA (10 eq) are added to the 2-chlorotrityl resin in 2 mL DCM. The mixture is intermittently stirred manually during 24h. After that, 0.5 mL/g of MeOH are added to the reaction mixture to cap the remaining reactive points of the resin. After 15 minutes, the solution is filtered off and the resin is washed thoroughly with DCM, DMF and MeOH. Fmoc removal is achieved by treating the resin with 20% piperidine in DMF (1 x 5', 1 x 10' and 1 x 15'). For the coupling of Na-Fmoc-NY-alloc-L-2,4-diaminobutyric acid (Fmoc-L-Dab(alloc)-OH), 3 eq of the amino acid, 3 eq of the coupling agent DIC and 3 eq of oxyma pure are dissolved in a small amount of DMF and premixed for 2 minutes. The resulting mixture is added to the resin and the reaction is allowed to proceed for 60 minutes. To extent of the reaction is monitored using the Kaiser test. The Fmoc group is then removed by treatments with 20% piperidine in DMF (1 x 5', 1 x 10' and 1 x 15 '). After that, Fmoc- N-methyl-L-iso leucine (Fmoc-NMe-L-Ile-OH) moiety is attached, for that purpose 3 eq of the amino acid, 3 eq of the coupling agent DIC and 3 eq of oxyma pure are dissolved in a small amount of DMF and premixed for 2 minutes. The resulting mixture is added to the resin and the reaction is allowed to proceed for 60 minutes. The extent of the reaction is monitored using the Kaiser test. The Fmoc group is then removed by treatments with 20% piperidine in DMF (1 x 5', 1 x 10' and 1 x 15 '). After that, Fmoc- trans-4-Fluoro-L-Proline (Fmoc-L-(F)Pro-OH) moiety is attached, for that purpose 3 eq of the amino acid, 3 eq of the coupling agent DIC and 3 eq of oxyma pure are dissolved in a small amount of DMF and premixed for 2 minutes. The resulting the mixture is added to the resin and the reaction is allowed to proceed for 60 minutes. The extent of the reaction is monitored using the Kaiser test. The Fmoc group is then removed by treatments with 20% piperidine in DMF (1 x 5', 1 x 10' and 1 x 15') and additional treatment with a mixture of piperidine/DBU/toluene/DMF (5:5:20:70) (1 x 5'). Hexanoic acid is coupled to the proline moiety by adding to the resin 3 eq of the acid, 3 eq of the coupling agent DIC and 3 eq of oxyma pure are dissolved in a small amount of DMF and premixed for 2 minutes. The resulting the mixture is added to the resin and the reaction is allowed to proceed for 60 minutes. Then the reaction is filtered off and the resin is rinsed thoroughly with DMF and DCM. The extent of the reaction is monitored using the chloranil test. For the removal of the Alloc group, 10 eq of phenylsilane in DCM are added to the resin while N2 is bubbled through the mixture. Then, 0.1 eq of Pd(PPh3)4 are added maintaining the N2 bubbling while mixing everything well. Then the reaction vessel is sealed and shaken for 15 minutes. After this time, the reaction is filtered and the resin washed thoroughly. The same treatment is repeated two more times. After the last treatment, the resin is washed thoroughly with DCM, MeOH and DMF. For the coupling of the benzoic acid on the side chain of the diaminoethyl moiety, 3 eq of said acid, 3 eq of the coupling agent DIC and 3 eq of oxyma pure are dissolved in a small amount of DMF and premixed for 2 minutes. The resulting mixture is added to the resin and the reaction is allowed to proceed for 60 minutes. After this time, the resin is washed with DMF and DCM and the extent of the reaction is monitored the Kaiser test. For the cleavage of the peptide, the resin is washed several times with DCM and dried by suction. The peptide is cleaved from the resin by adding a solution of DCM/TFA (95:5), the mixture is allowed to react for 15 min. Then the reaction mixture is filtered and the resin rinsed with DCM. This cleavage procedure is repeated twice. All the filtrates are pooled and the solvent is evaporated under vacuum, yielding example 16. The compound is purified using reverse-phase chromatography.
 

Historical Records