Fmoc-Tyr(tBu)-OH is a protected tyrosine derivative with the amino group protected by 9-fluorenylmethoxycarbonyl (Fmoc) and the phenolic hydroxyl group protected by tert-butyl (tBu), suitable for peptide synthesis.

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Quality Control of Fmoc-Tyr(tBu)-OH Purity: 98% SDS Specification

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Product Details of Fmoc-Tyr(tBu)-OH

CAS No. :	71989-38-3
Formula :	C₂₈H₂₉NO₅
M.W :	459.53
SMILES Code :	O=C(O)[C@H](CC1=CC=C(C=C1)OC(C)(C)C)NC(OCC2C3=C(C4=C2C=CC=C4)C=CC=C3)=O
MDL No. :	MFCD00037129
InChI Key :	JAUKCFULLJFBFN-VWLOTQADSA-N
Pubchem ID :	10895791

Safety of Fmoc-Tyr(tBu)-OH

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

Application In Synthesis of Fmoc-Tyr(tBu)-OH

* 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 [ 71989-38-3 ]

[ 71989-38-3 ] Synthesis Path-Downstream 1~36

1
[ 122889-11-6 ]
[ 35661-40-6 ]
[ 71989-38-3 ]
[ 35661-38-2 ]
Fmoc-Asp(OBzl)-OH [ No CAS ]
Tyr(tBu)-Asp(OBzl)-Phe-Phe-Ser(Bzl)-D-Ala [ No CAS ]

References: [1]Liebigs Annalen der Chemie,1993,p. 497 - 502.

2
[ 29022-11-5 ]
[ 35661-40-6 ]
[ 108-24-7 ]
[ 71989-38-3 ]
[ 198561-07-8 ]
Ac-Tyr-Asp-Phe-Gly-OH [ No CAS ]

References: [1]Organic Letters,2007,vol. 9,p. 2469 - 2472.

3
[ 68858-20-8 ]
[ 35661-40-6 ]
[ 71989-38-3 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 96402-49-2 ]
[ 143824-78-6 ]
Fmoc-S-trityl penicillamine [ No CAS ]
C₆₁H₇₆N₁₀O₁₀S₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 3927 - 3940.

4
Fmoc-Leu-Wang resin [ No CAS ]
[ 71989-31-6 ]
[ 71989-38-3 ]
[ 71989-26-9 ]
[ 132684-60-7 ]
[ 198561-07-8 ]
C₄₃H₆₉N₉O₉ [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 976 - 979.

5
fmoc-Leu-Alko Resin [ No CAS ]
[ 110-15-6 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 122889-11-6 ]
[ 71989-31-6 ]
[ 71989-38-3 ]
Cap₁-PLG-S(OBn)YL; Cap₁ = succinic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 853 - 856.

6
fmoc-Leu-Alko Resin [ No CAS ]
[ 123-43-3 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 122889-11-6 ]
[ 71989-31-6 ]
[ 71989-38-3 ]
[ 1218936-53-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 853 - 856.

7
fmoc-Leu-Alko Resin [ No CAS ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 121-53-9 ]
[ 122889-11-6 ]
[ 71989-31-6 ]
[ 71989-38-3 ]
Cap₃-PLG-S(OBn)YL; Cap₃ = 3-sulfobenzoic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 853 - 856.

8
fmoc-Leu-Alko Resin [ No CAS ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 122889-11-6 ]
[ 71989-31-6 ]
[ 71989-38-3 ]
[ 64-19-7 ]
Ac-PLG-S(OBn)YL [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 853 - 856.

9
Fmoc-Leu-Wang resin [ No CAS ]
[ 71989-31-6 ]
[ 71989-23-6 ]
[ 71989-38-3 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 198561-07-8 ]
[ 1198076-80-0 ]

References: [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 976 - 979.

10
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 71989-38-3 ]
[ 77128-73-5 ]
H-Tyr-Gly-Gly-(NMe)Phe-Leu-OH [ No CAS ]

References: [1]ACS Chemical Neuroscience,2013,vol. 4,p. 1204 - 1216.

11
[ 159610-89-6 ]
[ 68858-20-8 ]
[ 71989-38-3 ]
[ 71989-26-9 ]
[ 77284-32-3 ]
[ 94744-50-0 ]
N,N'-bis(tert-butyloxycarbonyl)-L-lysine dicyclohexylamine salt [ No CAS ]
[ 198561-07-8 ]
[ 1443329-49-4 ]

References: [1]Journal of Peptide Science,2013,vol. 19,p. 423 - 432.

12
[ 29022-11-5 ]
[ 71989-31-6 ]
[ 71989-18-9 ]
[ 71989-38-3 ]
[ 132388-59-1 ]
[ 132327-80-1 ]
(S)-6-[(Diphenyl-p-tolyl-methyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid [ No CAS ]
[ 58-85-5 ]
[ 198561-07-8 ]
C₆₆H₉₄N₂₀O₂₁S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: 4.1.1. Peptide synthesis; 4.1.2; Solid-phase peptide synthesis (SPPS) was performed with standardFmoc chemistry on rink amide resin using an automated peptidesynthesizer (Syro I, Multisyntech). The resin was loaded into a5 mL reactor with a frit at the bottom. Swelling was performed bydispensing 1 mL DMF and incubating for 15 min (2) with 10 sshaking every minute. Fmoc deprotection was achieved by treatmentwith 40percent piperidine DMF for 3 min and 20percent piperidine inDMF for 12 min (10 s/min shaking). Peptide couplings were carriedout by double couplings with Fmoc-protected amino acids(5 equiv), HBTU (5 equiv), HOBt (5 equiv) and DIPEA (10 equiv) inDMF for 40 min (10 s/min shaking). At the respective position,Fmoc-F2Pmp-OH (3 equiv) was coupled in DMF (1 mL) by manualaddition using TBTU (3 equiv), HOBt (3 equiv) and DIPEA (6 equiv)for 3 h, after 3 min preactivation. In case of the sequences for which side-chain labeling with biotinor carboxyfluorescein was planned, an additional 4-methyltrityl-(Mtt-) protected lysine was coupled to the N-terminus. Toselectively remove the Mtt group the resin was washed for 1 minwith DCM (3), deprotection was then achieved by treatment with1.8percent TFA in DCM for 3 min (10). During the deprotection the DCMsolution turned yellow.For fluorescein-labeling of the amine side-chain 5(6)-carboxyfluorescein(3 equiv), HATU (3 equiv), HOAt (3 equiv) andDIPEA (6 equiv) were dissolved in DMF and pre-activated for3 min. The solution was aspirated and coupling was allowed toproceed for 1 h. This step was repeated 4 times.For biotin-labeling of the amine side-chain the resin waswashed for 1 min in NMP (3). D-(+)-Biotin (3 equiv), HATU(3 equiv), HOAt (3 equiv) and DIPEA (6 equiv) were dissolved inNMP and pre-activated for 3 min. The solution was aspirated andcoupling was allowed to proceed for 2 h. This step was repeated2 times. N-terminal acetylation (where applicable) was achieved by dispensing800 lL of a mixture of acetic anhydride/pyridine (1:9) andreaction twice for 5 min (10 s/min shaking). After each deprotection,coupling or acetylation step, 5 washings (1 min each) withDMF were performed (10 s/min shaking).After synthesis the resin was transferred in a 5 mL syringeequipped with a frit, washed with DCM for 1 min (3) and driedin high vacuum for at least 30 min. For cleavage 1 mL of a mixtureof TFA and TIS (20:1) was added. The syringe with the mixture waskept on a shaker for 3 h. Then the liquid phase was filtered into20 mL of ice-cold Et2O. Formed precipitate was centrifuged,washed with ice-cold Et2O (2 20 mL) and purified by HPLC. 4.1.2. Azide functionalization of the N-terminus; To the peptides with the longer carbon linker, 6-azidohexanoicacid was coupled (with standard coupling conditions) to the Nterminalamine.The N-terminal amine of the peptides with the shorter linkerwas converted to an azide functionality directly on solid support.Using the compound imidazole-1-sulfonyl-azideHCl (synthesissee beneath) and modified conditions, which were reported forsolution phase chemistry from Goddard?Borger and Stick:8 Theresin was washed for 1 min each with DCM (2), DCM/MeOH(2) and MeOH (3). Then (for 40 mg resin, loading= 0.62 mmole/g) 1.4 equiv of imidazole-1-sulfonyl-azideHClin 1 mL MeOH and 100 ll of a saturated and centrifuged solutionof CuSO4*5H2O was added. After 1 min, DIPEA (1.8 equiv) wasadded and the coupling was allowed to proceed for 1 h andrepeated once more with an intermediate washing with MeOH(3 1 min).

References: [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 2848 - 2853.

13
[ 79598-53-1 ]
[ 29022-11-5 ]
[ 71989-31-6 ]
[ 71989-18-9 ]
[ 71989-38-3 ]
[ 132388-59-1 ]
[ 132327-80-1 ]
(S)-6-[(Diphenyl-p-tolyl-methyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid [ No CAS ]
[ 58-85-5 ]
[ 198561-07-8 ]
C₇₂H₁₀₅N₂₁O₂₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: 4.1.1. Peptide synthesis; 4.1.2; Solid-phase peptide synthesis (SPPS) was performed with standardFmoc chemistry on rink amide resin using an automated peptidesynthesizer (Syro I, Multisyntech). The resin was loaded into a5 mL reactor with a frit at the bottom. Swelling was performed bydispensing 1 mL DMF and incubating for 15 min (2) with 10 sshaking every minute. Fmoc deprotection was achieved by treatmentwith 40percent piperidine DMF for 3 min and 20percent piperidine inDMF for 12 min (10 s/min shaking). Peptide couplings were carriedout by double couplings with Fmoc-protected amino acids(5 equiv), HBTU (5 equiv), HOBt (5 equiv) and DIPEA (10 equiv) inDMF for 40 min (10 s/min shaking). At the respective position,Fmoc-F2Pmp-OH (3 equiv) was coupled in DMF (1 mL) by manualaddition using TBTU (3 equiv), HOBt (3 equiv) and DIPEA (6 equiv)for 3 h, after 3 min preactivation. In case of the sequences for which side-chain labeling with biotinor carboxyfluorescein was planned, an additional 4-methyltrityl-(Mtt-) protected lysine was coupled to the N-terminus. Toselectively remove the Mtt group the resin was washed for 1 minwith DCM (3), deprotection was then achieved by treatment with1.8percent TFA in DCM for 3 min (10). During the deprotection the DCMsolution turned yellow.For fluorescein-labeling of the amine side-chain 5(6)-carboxyfluorescein(3 equiv), HATU (3 equiv), HOAt (3 equiv) andDIPEA (6 equiv) were dissolved in DMF and pre-activated for3 min. The solution was aspirated and coupling was allowed toproceed for 1 h. This step was repeated 4 times.For biotin-labeling of the amine side-chain the resin waswashed for 1 min in NMP (3). D-(+)-Biotin (3 equiv), HATU(3 equiv), HOAt (3 equiv) and DIPEA (6 equiv) were dissolved inNMP and pre-activated for 3 min. The solution was aspirated andcoupling was allowed to proceed for 2 h. This step was repeated2 times. N-terminal acetylation (where applicable) was achieved by dispensing800 lL of a mixture of acetic anhydride/pyridine (1:9) andreaction twice for 5 min (10 s/min shaking). After each deprotection,coupling or acetylation step, 5 washings (1 min each) withDMF were performed (10 s/min shaking).After synthesis the resin was transferred in a 5 mL syringeequipped with a frit, washed with DCM for 1 min (3) and driedin high vacuum for at least 30 min. For cleavage 1 mL of a mixtureof TFA and TIS (20:1) was added. The syringe with the mixture waskept on a shaker for 3 h. Then the liquid phase was filtered into20 mL of ice-cold Et2O. Formed precipitate was centrifuged,washed with ice-cold Et2O (2 20 mL) and purified by HPLC. 4.1.2. Azide functionalization of the N-terminus; To the peptides with the longer carbon linker, 6-azidohexanoicacid was coupled (with standard coupling conditions) to the Nterminalamine.The N-terminal amine of the peptides with the shorter linkerwas converted to an azide functionality directly on solid support.Using the compound imidazole-1-sulfonyl-azideHCl (synthesissee beneath) and modified conditions, which were reported forsolution phase chemistry from Goddard?Borger and Stick:8 Theresin was washed for 1 min each with DCM (2), DCM/MeOH(2) and MeOH (3). Then (for 40 mg resin, loading= 0.62 mmole/g) 1.4 equiv of imidazole-1-sulfonyl-azideHClin 1 mL MeOH and 100 ll of a saturated and centrifuged solutionof CuSO4*5H2O was added. After 1 min, DIPEA (1.8 equiv) wasadded and the coupling was allowed to proceed for 1 h andrepeated once more with an intermediate washing with MeOH(3 1 min).

References: [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 2848 - 2853.

14
[ 35661-60-0 ]
[ 35661-51-9 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 108-24-7 ]
[ 71989-38-3 ]
[ 132388-59-1 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
Ac-Tyr-Asn-Trp-Asn-Ser-Phe-azaGly-Leu-Arg-Tyr-NH₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 3459 - 3470.

15
[ 67-56-1 ]
H-Gly-(2-Cl)-Trt-pol [ No CAS ]
[ 35661-39-3 ]
[ 291754-76-2 ]
[ 122889-11-6 ]
[ 71989-31-6 ]
[ 71989-38-3 ]
[ 135673-97-1 ]
C₅₂H₇₅N₇O₁₄ [ No CAS ]

References: [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2301 - 2309.

16
[ 35661-60-0 ]
[ 71989-38-3 ]
[ 71989-26-9 ]
[ 198561-07-8 ]
Ac-YLXKLLKLLXKLLK-NH₂; X=propargyl glicine [ No CAS ]

References: [1]Chemical Communications,2015,vol. 51,p. 14314 - 14317.

17
[ 16937-99-8 ]
3-acetamido-N-(2-aminoethyl)propanamide hydrogen chloride [ No CAS ]
[ 71989-38-3 ]
[ 132388-59-1 ]
[ 1072-84-0 ]
Fmoc-D-Tyr(O-tBu)-OH [ No CAS ]
N²-(9-fluorenylmethyloxycarbonyl)-N³-(4-methyltrityl)-2,3-diaminopropanoic acid [ No CAS ]
Fmoc-D-4-Hpg(PG)-OH [ No CAS ]
C₅₀H₆₅N₁₃O₁₃ [ No CAS ]

References: [1]MedChemComm,2016,vol. 7,p. 132 - 140.

18
[ 16937-99-8 ]
3-acetamido-N-(2-aminoethyl)propanamide hydrogen chloride [ No CAS ]
[ 71989-38-3 ]
[ 132388-59-1 ]
[ 1072-84-0 ]
Fmoc-D-Tyr(O-tBu)-OH [ No CAS ]
Nα-Fmoc-Nδ-(methyltrityl)-L-ornithine [ No CAS ]
Fmoc-D-4-Hpg(PG)-OH [ No CAS ]
C₅₂H₆₉N₁₃O₁₃ [ No CAS ]

References: [1]MedChemComm,2016,vol. 7,p. 132 - 140.

19
[ 16937-99-8 ]
3-acetamido-N-(2-aminoethyl)propanamide hydrogen chloride [ No CAS ]
[ 71989-38-3 ]
[ 132388-59-1 ]
[ 1072-84-0 ]
Fmoc-D-Tyr(O-tBu)-OH [ No CAS ]
(S)-6-[(Diphenyl-p-tolyl-methyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid [ No CAS ]
Fmoc-D-4-Hpg(PG)-OH [ No CAS ]
C₅₃H₇₁N₁₃O₁₃ [ No CAS ]

References: [1]MedChemComm,2016,vol. 7,p. 132 - 140.

20
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 ]

Yield	Reaction Conditions	Operation 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.

References: [1]Patent: US9308236,2016,B2 .Location in patent: Page/Page column 1673.

21
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
N⁴-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N²-(9-fluorenylmethylcarbonyl)asparagine [ No CAS ]
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-23-6 ]
[ 71989-38-3 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 132327-80-1 ]
[ 109425-51-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 198561-07-8 ]
KCNTATCATQRLANFLVHSS-(α-propargylglycinyl)-NFGPILPPTNVGS-(N⁴-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)asparaginyl)-TY-NH₂ [ No CAS ]