Fmoc-Asp(OtBu)-OH | 4-tert-Butyl N-(fluoren-9-ylmethoxycarbonyl)-L-aspartate | Carboxylic Acids

Fmoc-Asp(OtBu)-OH is a protected aspartic acid derivative with the amino group protected by 9-fluorenylmethoxycarbonyl (Fmoc) and the carboxyl group esterified by tert-butyl, suitable for peptide synthesis.

Synonyms: 4-tert-Butyl N-(fluoren-9-ylmethoxycarbonyl)-L-aspartate; Fmoc-L-Asp(OtBu)-OH

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Quality Control of Fmoc-Asp(OtBu)-OH Purity: 98% SDS Specification

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Product Details of Fmoc-Asp(OtBu)-OH

CAS No. :	71989-14-5
Formula :	C₂₃H₂₅NO₆
M.W :	411.45
SMILES Code :	O=C(OC(C)(C)C)C[C@@H](C(O)=O)NC(OCC1C2=CC=CC=C2C3=CC=CC=C13)=O
Synonyms :	4-tert-Butyl N-(fluoren-9-ylmethoxycarbonyl)-L-aspartate; Fmoc-L-Asp(OtBu)-OH
MDL No. :	MFCD00037131
InChI Key :	FODJWPHPWBKDON-IBGZPJMESA-N
Pubchem ID :	2724635

Safety of Fmoc-Asp(OtBu)-OH

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

Application In Synthesis of Fmoc-Asp(OtBu)-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.

Upstream synthesis route of [ 71989-14-5 ]
Downstream synthetic route of [ 71989-14-5 ]

[ 71989-14-5 ] Synthesis Path-Upstream 1~1

1
[ 71989-14-5 ]
[ 209252-17-5 ]

References: [1] Synthesis, 1998, # 6, p. 837 - 841.
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 21, p. 7648 - 7662.
[3] Patent: US2014/39153, 2014, A1, .

[ 71989-14-5 ] Synthesis Path-Downstream 1~35

1
[ 20866-48-2 ]
[ 35661-40-6 ]
[ 71989-14-5 ]
[ 125238-99-5 ]
[ 110116-75-1 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 2094 - 2099.

2
[ 20866-48-2 ]
[ 71989-14-5 ]
[ 77128-73-5 ]
(R)-N₅-(tert.-butoxy-carbonyl)-N₂-(9-fluorenylmethoxycarbonyl)-ornithine [ No CAS ]
[ 106327-80-4 ]

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 2094 - 2099.

3
[ 122889-11-6 ]
[ 71989-14-5 ]
[ 35737-15-6 ]
[ 35661-38-2 ]
Cbz-His-OH [ No CAS ]
(R)-N-{(R)-2-Benzyloxy-1-[(R)-1-((S)-1-carbamoyl-ethylcarbamoyl)-2-(1H-indol-3-yl)-ethylcarbamoyl]-ethyl}-3-[(R)-2-benzyloxycarbonylamino-3-(1H-imidazol-4-yl)-propionylamino]-succinamic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 192 - 200.

4
[ 67-56-1 ]
[ 122889-11-6 ]
[ 71989-14-5 ]
[ 708-06-5 ]
Gly-Wang resin [ No CAS ]
(S)-N-[(S)-2-Benzyloxy-1-(methoxycarbonylmethyl-carbamoyl)-ethyl]-3-[1-(2-hydroxy-naphthalen-1-yl)-meth-(E)-ylidene]-amino}-succinamic acid tert-butyl ester [ No CAS ]

References: [1]Journal of the American Chemical Society,2004,vol. 126,p. 10676 - 10681.

5
[ 29022-11-5 ]
[ 35661-40-6 ]
[ 71989-14-5 ]
[ 108-24-7 ]
[ 198561-07-8 ]
Ac-Asp-Asp-Phe-Gly-OH [ No CAS ]

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

6
C₃₃H₃₄N₃O₅Pol [ No CAS ]
[ 29022-11-5 ]
[ 35661-39-3 ]
[ 122889-11-6 ]
[ 35661-40-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 71989-35-0 ]
[ 109425-51-6 ]
His-Ala-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Ser(OBn)-[2-amino-3-(biphenyl-4-yl)propanoyl]-NH₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 7788 - 7799.

7
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 108-24-7 ]
[ 71989-23-6 ]
[ 71989-16-7 ]
[ 91000-69-0 ]
[ 198561-07-8 ]
C₅₇H₉₃N₁₇O₂₂ [ No CAS ]

References: [1]Organic Letters,2011,vol. 13,p. 5604 - 5607.

8
[ 29022-11-5 ]
[ 71989-14-5 ]
[ 86123-10-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 198561-07-8 ]
[ 1424402-71-0 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 1853 - 1864.

9
[ 68858-20-8 ]
[ 35661-40-6 ]
[ 71989-14-5 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 96402-49-2 ]
[ 143824-78-6 ]
Fmoc-[β-dimethylcysteine](Trt)-OH [ No CAS ]
C₅₆H₇₂N₁₀O₁₁S₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 5965 - 5974.

10
[ 68858-20-8 ]
[ 35661-40-6 ]
[ 71989-14-5 ]
[ 103213-32-7 ]
[ 109425-55-0 ]
[ 96402-49-2 ]
1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan [ No CAS ]
Fmoc-[β-dimethylcysteine](Trt)-OH [ No CAS ]
C₅₅H₇₀N₁₀O₁₁S₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 5965 - 5974.

11
[ 35661-60-0 ]
[ 122889-11-6 ]
[ 71989-14-5 ]
[ 64-19-7 ]
[ 378247-75-7 ]
Fmoc-Glu(pg)-OH [ No CAS ]
C₃₈H₄₆N₆O₁₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Synthesis of NH2-ACC-Rink Amide resin. Preparation of ACC wascarried out as described previously according to Maly et al.18 To glass reactionvessel, 1 eq (6.24 mmol, 13 g) of Rink AM resin was added and stirred gentlyonce per 10 min in DCM for 1 h, and then filtered and washed 3 times with DMF.Fmoc-protecting group was removed using 20percent piperidine in DMF (5, 5, and25 min), filtered each time and washed with DMF (six times). Next, 2.50 eq of Fmoc-ACC-OH (15.6 mmol, 6.9 g) was preactivated with 2.50 eq HOBt monohydrate (15.6 mmol, 2.34 g) and 2.50 eq DICI (15.6 mmol, 2.0 ml) in DMFand mixture was added to the resin. Reaction was stirred gently for 24 h at room temperature. Resin was washed four times with DMF and reaction was repeatedusing 1.5 eq of above reagents to improve yield of ACC coupling to the resin. Afterreaction, resin was washed with DMF and Fmoc group was removed using 20percentpiperidine in DMF (5, 5, and 25 min), filtered and washed with DMF (six times). Synthesis of NH2-Asp(t-Bu)-ACC-Rink Amide resin. Next, 2.5 eqFmoc-Asp(t-Bu)-OH (15.6 mmol, 6.42 g) with 2.5 eq HATU (15.6 mmol, 5.93 g),2.5 eq collidine (15.6 mmol, 2.03 ml) in DMF were activated for 2 min and added tofilter cannula with 1 eq (6.24 mmol) NH2-ACC-resin and reaction was carried outfor 24 h. Next, resin was washed four times with DMF and reaction was repeatedusing 1.5 eq of above reagents. After washing with DMF, Fmoc-protecting groupwas removed using 20percent piperidine in DMF (5, 5, and 25 min). Resin wasadditional washed with DCM (3 times) and MeOH (3 times) and dried over P2O5. Synthesis of individual optimized substrates. The 2.5 eqFmoc-P2-OH was preactivated with 2.5 eq HOBt and 2.5 eq DICI in DMF andadded to cartridge with 1 eq NH2-Asp(t-Bu)-ACC-resin (all substrates containedAsp at P1 position) and followed by gentle agitation for 3 h. Then, it was filteredand washed with DMF (six times). Fmoc-protecting group was removed using 20percent piperidine in DMF (5, 5, and 25 min). Ninhydrin test was carried out each time aftercoupling and deprotection. A solution of 2.5 eq Fmoc-P3-OH, 2.5 eq HOBt, and2.5 eq DICI in DMF was added to the resin and the slurry was agitated for 3 h.After removal of the solution, the resin was washed with DMF (six times), andcoupling and deprotection of Fmoc-P4-OH was carried in identical conditions likeP2 position. N-terminus was protected with acetyl group using 5 eq AcOH, 5 eqHBTU, and 5 eq DIPEA in DMF as previous described. After solvent removal, theresin was washed with DMF (six times), DCM (three times), and MeOH (threetimes) dried over P2O5 and cleaved from the resin with a mixture of TFA/TIPS/H2O(percent, v/v/v 95 : 2.5 : 2.5). The crude product was purified by HPLC and lyophilized.Its purity was confirmed by analytical HPLC. Each optimized substrate wasanalyzed using HRMS. Optimized substrates were dissolved in peptide gradeDMSO to 20mM concentration and stored at -80 °Cuntil use.

References: [1]Cell Death and Differentiation,2014,vol. 21,p. 1482 - 1492.

12
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 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 ]
[ 132388-59-1 ]
[ 96402-49-2 ]
[ 109425-51-6 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
DCLGA-(L-1-naphthylalanyl)-RKCIPDNDKCCRPNLVCSRTHKWCKYVF-NH₂; disulfide linked (C2→C17, C9→C23, C16→C30) [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2299 - 2314.

13
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 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 ]
[ 96402-49-2 ]
[ 109425-51-6 ]
[ 143824-78-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
DCLGF-(L-1-naphthylalanyl)-RKCIPDNDKCCRPNLVCSRTHKWCKYVF-NH₂; disulfide linked (C2→C17, C9→C23, C16→C30) [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 2299 - 2314.

14
[ 1026023-54-0 ]
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 35661-39-3 ]
[ 71989-31-6 ]
[ 71989-33-8 ]
[ 71989-14-5 ]
[ 71989-18-9 ]
[ 556-08-1 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 109425-51-6 ]
[ 116821-47-7 ]
[ 198561-07-8 ]
[ 334918-39-7 ]
C₁₂₈H₂₁₈N₅₀O₃₆ [ No CAS ]