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Chemical Structure| 159611-02-6 Chemical Structure| 159611-02-6
Chemical Structure| 159611-02-6

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Fmoc-3-(2-Furyl)-Ala-OH is an alanine derivative that serves as a standard structural unit for amino acid residues in peptide synthesis.

Synonyms: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(furan-2-yl)propanoic acid

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Product Details of Fmoc-3-(2-Furyl)-Ala-OH

CAS No. :159611-02-6
Formula : C22H19NO5
M.W : 377.39
SMILES Code : O=C(O)[C@@H](NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)CC4=CC=CO4
Synonyms :
(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(furan-2-yl)propanoic acid
MDL No. :MFCD01311747
InChI Key :AJXDCHXGNUFBRC-FQEVSTJZSA-N
Pubchem ID :2734451

Safety of Fmoc-3-(2-Furyl)-Ala-OH

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of Fmoc-3-(2-Furyl)-Ala-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 [ 159611-02-6 ]
  • Downstream synthetic route of [ 159611-02-6 ]

[ 159611-02-6 ] Synthesis Path-Upstream   1~1

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  • [ 146725-85-1 ]
  • [ 28920-43-6 ]
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YieldReaction ConditionsOperation in experiment
53% With LiOH; sodium hydrogencarbonate In 1,4-dioxane c
(S)-2-(9-Fluorenylmethyloxycarbonylamino)-3-(2-furyl)-propionic acid
Methyl (S)-2-amino-3-(2-furyl)propionate (1 g, 6.5 mmol) was mixed with 2M LiOH (3.27 ml, 6.5 mmol) and dioxane (3.27 ml) at 0° C. and stirred overnight under N2.
The next day a TLC control (CHCl3 /MeOH/NH3 aq 1/1/0.1) of the reaction mixture showed no ester present. 1M NaHCO3 (9.75 ml, 9.75 mmol) and 9-fluorenylmethyloxycarbonyl chloride (2.5 g, 9.75 mmol) dissolved in dioxane (10 ml) were added to the above solution and the stirring continued for a further 1 hour.
Dioxane was removed under reduced pressure and the aqueous solution acidified with a 10percent KHSO4 solution to pH 2.
The solution was extracted with CHCl3 (3*20 ml), dried (MgSO4), evaporated and purified by flash chromatography (Hexane/ethyl acetate/acetic acid 10/10/1).
Yield: 1.3 g (53percent), white crystals.
1 H NMR (CDCl3): δ2.95 (dd, 1H, J 9.9, J 15.2 Hz), 3.08 (dd, 1H, J 4.4, J 15.2 Hz), 3.6 (br.s, 1H), 4.16-4.26 (m, 4H), 6.12 (d, 1H, J 2.9 Hz), 6.33 (t, 1H, J 2.3 Hz), 7.29 (t, 2H, J 7.32 Hz), 7.39 (t, 2H, J 7.48 Hz), 7.49 (br.s, 1H), 7.64 (dd, 2H, J 7.17, J 2.14 Hz), 7.85 (d, 2H, J 7.48 Hz).
13 C NMR (CDCl3): δ29.8, 46.98, 66.04, 107.45, 110.85, 120.48, 125.57, 125.63, 127.50, 128.07, 141.06, 142.21, 144.09, 151.84, 156.26, 160.35.
References: [1] Patent: US5629293, 1997, A, .
 

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