Structure of Fmoc-Glu-OMe
CAS No.: 145038-49-9
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| CAS No. : | 145038-49-9 |
| Formula : | C21H21NO6 |
| M.W : | 383.39 |
| SMILES Code : | O=C(O)CC[C@H](NC(OCC1C2=C(C3=C1C=CC=C3)C=CC=C2)=O)C(OC)=O |
| MDL No. : | MFCD21607506 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H315-H319-H335 |
| Precautionary Statements: | P261-P305+P351+P338 |
* 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.

[ 145038-49-9 ]
[ 543-27-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With triethylsilane; trifluoroacetic acid; In dichloromethane; at 20℃; | General procedure: A dichloromethane solution (10 mL) of Fmoc-AA(OtBu)-OMe (0.3 mmol) was treated with trifluoroacetic acid (1.5 mL) and triethylsilane (0.25 mL) at room temperature. After a check of TLC showed that the starting tert-butyl ether had disappeared (stirring for 2?3 h), the reaction was quenched by addition of distilled water. The separated organic phase was washed with water, dried over sodium sulfate, and filtered. All the solvent was evaporated and the residue was purified with FCC (10 percent Et2O?CH2Cl2) and recrystallization (CH2Cl2?hexane) to give 5d/e (ca. 50?70 percent). |

[ 18107-18-1 ]
[ 145038-49-9 ]
[ 145038-49-9 ]


| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 33%; 13%; 33% | In dichloromethane; at 20℃;Inert atmosphere; Darkness; | General procedure: A dichloromethane solution (15 mL) of epoxide 4 (28.2 mg, 50 mumol) and Fmoc-AA(OH)-OMe 5 or ROH 6 (250 mumol, 5 equiv) with(out) p-toluenesulfonic acid monohydrate (pTSA, 1 mg, 0.1 equiv) was stirred at room temperature in the dark under nitrogen: in the case of carboxylic acids 5d/ e, pTSA was not necessary as the catalytic additive. After the disappearance of 4 determined by checking TLC (stirring for 1?3 h), the reaction was quenched by addition of distilled water. The separated organic phase was washed with an aqueous saturated sodium bicarbonate solution and water, dried over sodium sulfate, and filtered. All the solvent was evaporated and the residue was purified with FCC (5?10 percent Et2O?CH2Cl2 or 50 percent AcOEt?hexane) and recrystallization (CH2Cl2?hexane) to give desired conjugates 1?3 as analytically pure black solids. All the samples were purified by HPLC (1 percent THF-14 percent H2O?CH3CN) just before their optical measurements. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; for 8h; | Synthesis of 1-155 Compound 1-153 (1.14 g, 3.44 mmol), compound 4444 (N-9-fluorenylmethoxycarbonylglutamic acid alpha-methyl ester, commercially available) (1.72 g, 4.47 mmol), and HBTU (1.96 g, 5.16 mmol) were dissolved in 50 mL of DCM:DMF (8:2). DIEA (1.78 g, 13.8 mmol) was added and the reaction stirred for 8 h. The volatiles were removed in vacuo and the residue was dissolved in DCM and extracted with sat. NH4Cl (2×), sat. NaHCO3 (2×) and water (2×). The organic layer was dried over Na2SO4 and evaporated to dryness. The residue was purified by silica gel chromatography (8:2, EtOAc:Hex) to give 1-155. 1H NMR (CDCl3, 500 MHz) delta 7.79-7.05 (m, 15H), 6.59 (d, J=7.5 Hz, 1H), 5.81 (br s, 1H), 5.78 (d, J=5 Hz, 1H), 5.17 (d, J=13.5 Hz, 1H), 5.08 (m, 1H), 4.35-4.2 (m, 3H), 4.17 (m, 1H), 3.69-2.85 (diastereomeric Me, 9H), 2.15 (br m, 2H), 1.99-1.89 (m, 2H). 13C NMR (CDCl3, 100 MHz) delta 172.5, 169.9, 156.4, 146.5, 145.3, 143.93, 143.91, 143.8, 143.4, 141.4, 136.0, 135.8, 129.0, 128.6, 127.8, 127.22, 127.20, 127.17, 125.3, 125.23, 125.20, 124.9, 120.7, 120.12, 120.11, 120.05, 119.9, 119.5, 117.2, 113.3, 112.8, 112.7, 105.4, 72.5, 66.94, 66.91, 53.6, 53.5, 52.7, 50.0, 47.3, 44.5, 33.4, 33.3, 32.2, 28.5, 28.4. HRMS (ESI) calcd. for C41H41BN4O6 [M+H] 696.3229, found 696.3253. |