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CAS No. : | 1025434-04-1 | MDL No. : | MFCD02682488 |
Formula : | C19H17NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WKYFUFWCJIKRCS-KRWDZBQOSA-N |
M.W : | 323.34 | Pubchem ID : | 66601066 |
Synonyms : |
|
Chemical Name : | (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)but-3-enoic acid |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 | UN#: | N/A |
Hazard Statements: | H302-H312-H332 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride In dichloromethane at 20 - 40℃; for 2h; | ||
With thionyl chloride In dichloromethane at 0℃; for 3h; Reflux; Inert atmosphere; | ||
With thionyl chloride In dichloromethane at 0℃; for 3h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In 1,4-dioxane at 80℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: SOCl2 / CH2Cl2 / 2 h / 20 - 40 °C 2: 78 percent / CH2Cl2 / 16 h / 20 °C 3: 99 percent / Ru-containing catalyst / CH2Cl2 / 16 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: SOCl2 / CH2Cl2 / 2 h / 20 - 40 °C 2: 78 percent / CH2Cl2 / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: SOCl2 / CH2Cl2 / 2 h / 20 - 40 °C 2: 65 percent / CH2Cl2 / 16 h / 20 °C 3: 94 percent / Ru-containing catalyst / CH2Cl2 / 16 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: SOCl2 / CH2Cl2 / 2 h / 20 - 40 °C 2: 77 percent / CH2Cl2 / 16 h / 20 °C 3: 99 percent / Ru-containing catalyst / CH2Cl2 / 16 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: SOCl2 / CH2Cl2 / 2 h / 20 - 40 °C 2: 65 percent / CH2Cl2 / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: SOCl2 / CH2Cl2 / 2 h / 20 - 40 °C 2: 77 percent / CH2Cl2 / 16 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: NaIO4 / methanol; H2O / 20 h / 0 - 20 °C 2: xylene / 72 h / 150 °C 3: aq. HCl / dioxane / 48 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: xylene / 72 h / 150 °C 2: aq. HCl / dioxane / 48 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide Automated synthesizer; solid phase reaction; Stage #2: solid phase reaction; Stage #3: Fmoc-Leu-OH; Fmoc-Ile-OH; Fmoc-Lys(tert-butoxycarbonyl); Fmoc-Thr(tBu)-OH; N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-methionine; L-Asn(Trt); Fmoc-L-Gln(Trt)-OH; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; (S)-N-(Fmoc)vinylglycine Further stages; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: boron trifluoride diethyl etherate / dichloromethane; cyclohexane / Inert atmosphere 2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
933 mg | With boron trifluoride diethyl etherate In dichloromethane; cyclohexane Inert atmosphere; | 4.2.1 Cross-metathesis between allylglycine and vinylglycine derivatives General procedure: A solution of allylglycine derivative (0.50mmol) and vinylglycine derivative (0.90mmol) in dichloromethane (6mL) wasbubbled with Ar for 5min, and then cannulated into a flask containing the Grubbs' second generation catalyst (10mol%). Thereaction mixture was refluxed overnight. The mixture was concentrated in vacuo and the residue was purified by flash silica gel column chromatography (eluent: hexane/ethyl acetate 8:1 v/v) to afford the cross-coupled products 9 or 10, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; In 1,4-dioxane; water;Inert atmosphere; Reflux; | General procedure: A solution of allylglycine derivative (0.50mmol) and vinylglycine derivative (0.90mmol) in dichloromethane (6mL) wasbubbled with Ar for 5min, and then cannulated into a flask containing the Grubbs' second generation catalyst (10molpercent). Thereaction mixture was refluxed overnight. The mixture was concentrated in vacuo and the residue was purified by flash silica gel column chromatography (eluent: hexane/ethyl acetate 8:1 v/v) to afford the cross-coupled products 9 or 10, respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux; Inert atmosphere 2: dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux; Inert atmosphere 2: dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux; Inert atmosphere 2: dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 3: Grubbs catalyst first generation / dichloromethane / 72 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux; Inert atmosphere 2: dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 3: Grubbs catalyst first generation / dichloromethane / 48 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux; Inert atmosphere 2: dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 3: Grubbs catalyst first generation / dichloromethane / 72 h / Inert atmosphere; Reflux 4: trifluoroacetic acid / dichloromethane / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux; Inert atmosphere 2: dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 3: Grubbs catalyst first generation / dichloromethane / 48 h / Inert atmosphere; Reflux 4: trifluoroacetic acid / dichloromethane / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux; Inert atmosphere 2: dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 3: Grubbs catalyst first generation / dichloromethane / 72 h / Inert atmosphere; Reflux 4: trifluoroacetic acid / dichloromethane / Inert atmosphere 5: iodine; [bis(acetoxy)iodo]benzene / acetonitrile / 0.5 h / 80 °C / Inert atmosphere; Darkness |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux 2: dichloromethane / 3 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux 2: dichloromethane / 3 h / 0 - 20 °C 3: Grubbs catalyst first generation / dichloromethane / 48 h / Reflux 4: trifluoroacetic acid / dichloromethane 5: iodine / toluene / 0.5 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux 2: dichloromethane / 3 h / 0 - 20 °C 3: Grubbs catalyst first generation / dichloromethane / 48 h / Reflux 4: trifluoroacetic acid / dichloromethane 5: 1-<bis(adamantylcarbonyloxy)iodo>-4-methoxybenzene; iodine / toluene / 0.5 h / 80 °C / Darkness |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux 2: dichloromethane / 3 h / 0 - 20 °C 3: Grubbs catalyst first generation / dichloromethane / 48 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux 2: dichloromethane / 3 h / 0 - 20 °C 3: Grubbs catalyst first generation / dichloromethane / 48 h / Reflux 4: trifluoroacetic acid / dichloromethane |