96402-49-2|Fmoc-1-Nal-OH| Ambeed

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Quality Control of Fmoc-1-Nal-OH Purity: 98% SDS Specification

COA

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NMR

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CNMR

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Product Details of Fmoc-1-Nal-OH

CAS No. :	96402-49-2
Formula :	C₂₈H₂₃NO₄
M.W :	437.49
SMILES Code :	[H][C@@](CC1=CC=CC2=C1C=CC=C2)(NC(=O)OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)C(O)=O
MDL No. :	MFCD00151914
InChI Key :	ORWNVJDLEMVDLV-SANMLTNESA-N
Pubchem ID :	2734474

Safety of Fmoc-1-Nal-OH

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

Application In Synthesis of Fmoc-1-Nal-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 [ 96402-49-2 ]

[ 96402-49-2 ] Synthesis Path-Downstream 1~35

1
[ 28920-43-6 ]
[ 55516-54-6 ]
[ 96402-49-2 ]

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 2 - 10.

2
[ 108-24-7 ]
[ 91000-69-0 ]
[ 96402-49-2 ]
[ 109425-51-6 ]
[ 143824-78-6 ]
Ac-His-Nal(1')-Arg-Trp-NH₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 3073 - 3081.

3
[ 108-24-7 ]
[ 86123-10-6 ]
[ 96402-49-2 ]
[ 109425-51-6 ]
Fmoc-Arg(Pbf)-OH [ No CAS ]
Ac-His-D-Phe-Arg-Nal(1')-NH₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 5736 - 5744.

4
[ 66-77-3 ]
[ 67436-13-9 ]
[ 96402-49-2 ]
[ 541-88-8 ]
(R)-N-α-Fmoc-N-ε-Boc-lysinal [ No CAS ]
(S)-2-{(R)-6-(4-Amino-butyl)-9-[(naphthalen-1-ylmethyl)-amino]-3,8-dioxo-[1,4,7]thiadiazecan-4-yl}-3-naphthalen-1-yl-propionic acid [ No CAS ]
(S)-2-{(R)-6-(4-Amino-butyl)-9-[(naphthalen-1-ylmethyl)-amino]-3,8-dioxo-[1,4,7]thiadiazecan-4-yl}-3-naphthalen-1-yl-propionamide [ No CAS ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 11046 - 11055.

5
[ 66-77-3 ]
[ 67436-13-9 ]
[ 96402-49-2 ]
[ 541-88-8 ]
(S)-N-α-Fmoc-N-ε-Boc-lysinal [ No CAS ]
(S)-2-{(R)-6-(4-Amino-butyl)-9-[(naphthalen-1-ylmethyl)-amino]-3,8-dioxo-[1,4,7]thiadiazecan-4-yl}-3-naphthalen-1-yl-propionic acid [ No CAS ]
(S)-2-{(R)-6-(4-Amino-butyl)-9-[(naphthalen-1-ylmethyl)-amino]-3,8-dioxo-[1,4,7]thiadiazecan-4-yl}-3-naphthalen-1-yl-propionamide [ No CAS ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 11046 - 11055.

6
[ 66-77-3 ]
[ 67436-13-9 ]
[ 96402-49-2 ]
[ 541-88-8 ]
(S)-N-α-Fmoc-N-ε,N-γ-di-Boc-arginal [ No CAS ]
(S)-2-{(R)-6-(3-Guanidino-propyl)-9-[(naphthalen-1-ylmethyl)-amino]-3,8-dioxo-[1,4,7]thiadiazecan-4-yl}-3-naphthalen-1-yl-propionamide [ No CAS ]
(S)-2-{(R)-6-(3-Guanidino-propyl)-9-[(naphthalen-1-ylmethyl)-amino]-3,8-dioxo-[1,4,7]thiadiazecan-4-yl}-3-naphthalen-1-yl-propionic acid [ No CAS ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 11046 - 11055.

7
[ 29022-11-5 ]
[ 96402-49-2 ]
N-[(9-fluorenyl)methoxycarbonyl]-3-(2-naphthyl)-D-alanine [ No CAS ]
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(3-thienyl)propanoic acid [ No CAS ]
Fmoc-Arg(Pbf)-Wang resin [ No CAS ]
C₇₀H₉₁N₁₉O₁₂S₂ [ No CAS ]

References: [1]Polish Journal of Chemistry,2003,vol. 77,p. 881 - 887.

8
[ 96402-49-2 ]
[ 4942-47-6 ]
N-[(9-fluorenyl)methoxycarbonyl]-3-(2-naphthyl)-D-alanine [ No CAS ]
N-(9-fluorenylmethoxycarbonyl)-(2S,4S)-4-tert-butoxyproline [ No CAS ]
Fmoc-Arg(Pbf)-Wang resin [ No CAS ]
C₈₂H₁₀₇N₁₉O₁₃S₂ [ No CAS ]

References: [1]Polish Journal of Chemistry,2003,vol. 77,p. 881 - 887.

9
[ 68858-20-8 ]
[ 35661-39-3 ]
[ 71989-31-6 ]
[ 96402-49-2 ]
Fmoc-Tyr(t-Bu)-NH-resin [ No CAS ]
(S)-2-[(S)-2-({(S)-1-[(S)-2-((S)-2-Amino-propionylamino)-3-methyl-butyryl]-pyrrolidine-2-carbonyl}-amino)-3-naphthalen-1-yl-propionylamino]-3-(4-hydroxy-phenyl)-propionic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 4417 - 4426.

10
[ 67-56-1 ]
[ 71989-14-5 ]
[ 96402-49-2 ]
[ 708-06-5 ]
Gly-Wang resin [ No CAS ]
(S)-3-[1-(2-Hydroxy-naphthalen-1-yl)-meth-(E)-ylidene]-amino}-N-[(S)-1-(methoxycarbonylmethyl-carbamoyl)-2-naphthalen-1-yl-ethyl]-succinamic acid tert-butyl ester [ No CAS ]

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

11
[ 67-56-1 ]
[ 96402-49-2 ]
[ 77284-32-3 ]
[ 708-06-5 ]
Gly-Wang resin [ No CAS ]
[(S)-2-((S)-2-[1-(2-Hydroxy-naphthalen-1-yl)-meth-(E)-ylidene]-amino}-3-naphthalen-1-yl-propionylamino)-hexanoylamino]-acetic acid methyl ester [ No CAS ]

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

12
[ 591-80-0 ]
[ 29022-11-5 ]
[ 96402-49-2 ]
((S)-3-Naphthalen-1-yl-2-pent-4-enoylamino-propionylamino)-acetic acid [ No CAS ]

References: [1]Organic Letters,2005,vol. 7,p. 2695 - 2698.

13
[ 112883-29-1 ]
[ 96402-49-2 ]
[ 73731-37-0 ]
[ 35737-15-6 ]
N-Fmoc-L-Pro-2-chlorotrityl polystyrene resin [ No CAS ]
N-Fmoc-L-Phe [ No CAS ]
cyclo(1-Nal-D-Trp-Tyr-Thr-Phe-Pro) [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 551 - 559.

14
[ 71989-31-6 ]
[ 35661-40-6 ]
[ 2491-06-7 ]
[ 96402-49-2 ]
piperazine [ No CAS ]
C₃₅H₄₄N₆O₄ [ No CAS ]

References: [1]Organic Letters,1999,vol. 1,p. 345 - 347.

15
[ 96402-49-2 ]
C₃₆H₄₆N₆O₄ [ No CAS ]

References: [1]Organic Letters,1999,vol. 1,p. 345 - 347.

16
[ 96402-49-2 ]
C₃₆H₅₄N₆ [ No CAS ]

References: [1]Organic Letters,1999,vol. 1,p. 345 - 347.

17
[ 35661-40-6 ]
[ 96402-49-2 ]
[ 183673-66-7 ]
C₇₃H₇₈N₁₁O₁₀Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Each of the reaction wells contained 0.0675 mmol of Rink Amide MBHA resin(substitution = 0.72 mmol/g, Novabiochem, San Diego, CA). The following Fmoc amino acids (Novabiochem, San Diego, CA; Chem-Impex International, Wood Dale, IL; SyntheTech, Albany, OR; Pharma Core, High Point, NC) were used: Fmoc-Lys(Boc)-OH, EPO <DP n="112"/>Fmoc-Phe-OH, Fmoc-H-Inp-OH, Fmoc-D-lNal-OH, Fmoc-D-2Nal-OH, Fmoc-D- TrP(BoC)-OH, Fmoc-3Pal-OH, Fmoc-4Pal-OH/ FmOc-Om(BoC)-OH, Fmoc-D-Bip-OH, FmOC-ThT(BzI)-OH, Fmoc-Pff-OH, Fmoc-2Thi-OH, Fmoc-Taz-OH, Fmoc-D-Dip-OH, Fmoc-D-Bpa-OH, Fmoc-D-Bal-OH, and Fmoc-Apc(Boc)-OH.Each of the Fmoc amino acids was dissolved in a 0.3 N solution of HOBt in DMF wherein the concentration of the resulting Fmoc amino acid was 0.3 N. A four fold excess (0.27 mmol, 0.9 mL of the 0.3 N solution) of Fmoc amino acid was used for each coupling. DIC (0.27 mmol, 0.6 mL of 0.45N DIC solution in DMF) was used as the coupling reagent for each coupling. Deprotection was performed by using 20percent piperidine in DMF (2 X 1.5 mL per residue). The peptides were cleaved from the resin by treating the peptide-resins with 8percent trsopropylsilane (TIP) in trifluoroacetic acid (TFA) (1.5 mL per reaction well) at room temperature for 2h. The resin was removed by filtration. Each filtrate was diluted to 25 mL with ether in a centrifuge tube. The resulting precipitate in each tube was centrifuged and the solvents were decanted from the precipitate. The precipitate in each tube was then dissolved in methanol (3 mL) and diluted with water (1 mL). The purification of the crude products was done on a reverse-phase preparative HPLC using a column (100 X 21.20 mm, 5mu) of LUNA 5mu C8(2) (Phenomenex, Torrance, CA). For each peptide, the column was eluted with a linear gradient from 85percent A and 15percent B to 25percent A and 75percent B in 15 min with a flow rate of 25 mL/min. A was 0.1percent TFA in water and B was 0.1percent TFA in acetonitrile/water (80/20, v/v). The fractions were checked by analytical HPLC and those containing the pure product were combined and lyophilized to dryness.Yields ranged from 13percent to 71percent and purity of each of Examples 1 - 65 exceeded 94percent based upon analytical HPLC analysis. Electro-spray ionization mass spectrometry (ES-MS) analysis was performed and observed molecular weights were in agreement with calculated molecular weights. The results are detailed in Table I, below

References: [1]Patent: WO2007/41278,2007,A2 .Location in patent: Page/Page column 110-111.

18
[ 96402-49-2 ]
[ 252279-09-7 ]
C₄₇H₃₉N₅O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; In dichloromethane; for 0.166667h;	The forgoing solution of the intermediate product IB was divided into four equal portions and coupled with the pre-activated HOBT esters of FMOC protected amino acids, as summarized in reaction schemes 1C, ID, IE, and IF, below. The amino acid used: FMOC-D-2Nal-OH (130mg, 0.30mmole) (Synthetech Albany, Oregon) Each of the immediately foregoing amino acids was pre-activated with HOBT (46mg, 0.30mmole) and DIC (38mg, 0.30mmole) in DCM (5ml) for ten minutes before addition to one of the four portions of the forgoing solution of the intermediate product IB. The coupling reaction was then allowed to proceed for 30 minutes at room temperature.

References: [1]Patent: WO2007/41278,2007,A2 .Location in patent: Page/Page column 113-114.

19
Fmoc-Rink resin [ No CAS ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 71989-33-8 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 96402-49-2 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
C₁₇₅H₂₁₄N₂₁O₂₄PolS₃ [ No CAS ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 14625 - 14633.

20
Fmoc-Rink resin [ No CAS ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 71989-33-8 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 132327-80-1 ]
[ 96402-49-2 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
C₁₃₁H₁₇₆N₁₉O₂₂PolS [ No CAS ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 14625 - 14633.

21
Fmoc-Rink resin [ No CAS ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 96402-49-2 ]
[ 118358-38-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
C₁₈₅H₂₂₄N₂₁O₃₃PolS₃ [ No CAS ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 14625 - 14633.

22
Fmoc-Rink resin [ No CAS ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 132327-80-1 ]
[ 96402-49-2 ]
[ 118358-38-6 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
C₁₄₁H₁₈₆N₁₉O₃₁PolS [ No CAS ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 14625 - 14633.

23
Fmoc-Rink resin [ No CAS ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 108-24-7 ]
[ 71989-35-0 ]
[ 132388-59-1 ]
[ 96402-49-2 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
C₇₇H₉₉N₁₂O₁₃PolS [ No CAS ]

References: [1]Journal of the American Chemical Society,2008,vol. 130,p. 14625 - 14633.

24
Hydroxymethyl resin [ No CAS ]
[ 96402-49-2 ]
C₂₉H₂₄NO₄Pol [ No CAS ]

References: [1]Chemistry - A European Journal,2008,vol. 14,p. 6406 - 6412.

25
C₄₈H₅₂N₃O₇PolS [ No CAS ]
[ 96402-49-2 ]
C₇₆H₇₃N₄O₁₀PolS [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 6639 - 6641.

26
C₆₁H₆₃N₄O₈PolS [ No CAS ]
[ 96402-49-2 ]
C₈₉H₈₄N₅O₁₁PolS [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 6639 - 6641.

27
[ 29022-11-5 ]
[ 35661-60-0 ]
[ 71989-23-6 ]
[ 71989-26-9 ]
[ 96402-49-2 ]
Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine [ No CAS ]
[ 1160810-26-3 ]

References: [1]Heterocycles,2009,vol. 79,p. 925 - 933.

28
[ 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.

29
[ 68858-20-8 ]
[ 35661-40-6 ]
[ 71989-38-3 ]
[ 103213-32-7 ]
[ 109425-55-0 ]
[ 96402-49-2 ]
1-tert-butoxycarbonyl-N-[(9-fluorenyl)methoxycarbonyl]-D-tryptophan [ No CAS ]
Fmoc-S-trityl penicillamine [ No CAS ]
C₆₀H₇₄N₁₀O₁₀S₂ [ No CAS ]

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

30
knorr amide resin [ No CAS ]
[ 29022-11-5 ]
[ 68858-20-8 ]
[ 35661-60-0 ]
[ 71989-38-3 ]
[ 71989-26-9 ]
[ 103213-32-7 ]
[ 96402-49-2 ]
[ 109425-56-1 ]
(2S,4R)-4-tert-butoxy-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid [ No CAS ]
UGVCCGYKLC[NAL]OC-NH₂; O = L-trans-hydroxyproline; U = L-pyroglutamic acid; [NAL] = L-1-naphthylalanine [ No CAS ]