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[ CAS No. 67561-03-9 ] {[proInfo.proName]}

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Chemical Structure| 67561-03-9
Chemical Structure| 67561-03-9
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Product Details of [ 67561-03-9 ]

CAS No. :67561-03-9 MDL No. :MFCD06008302
Formula : C10H11NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 193.20 Pubchem ID :-
Synonyms :

Safety of [ 67561-03-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 67561-03-9 ]

* 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 [ 67561-03-9 ]

[ 67561-03-9 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 67561-03-9 ]
  • [ 95061-51-1 ]
  • (1'S,3S)-4-<(Benzyloxycarbonyl)amino>-3-hydroxybutanoic acid 2'-hydroxy-1',2',2'-triphenylethyl ester [ No CAS ]
  • (1'S,3R)-4-<(Benzyloxycarbonyl)amino>-3-hydroxybutanoic acid 2'-hydroxy-1',2',2'-triphenylethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With lithium diisopropyl amide 1.) THF, hexane, O deg C, 30 min, 2.) -80 deg C to -84 deg C, 2 h; Multistep reaction. Title compound not separated from byproducts;
  • 2
  • [ 67561-03-9 ]
  • [ 95061-47-5 ]
  • [ 126832-13-1 ]
  • 3
  • [ 67561-03-9 ]
  • [ 95061-47-5 ]
  • [ 126832-14-2 ]
  • [ 126832-13-1 ]
  • 4
  • [ 114790-39-5 ]
  • [ 67561-03-9 ]
YieldReaction ConditionsOperation in experiment
50% With oxalic acid; In tetrahydrofuran; hexane; water; ethyl acetate; N-Benzyloxycarbonyl Aminoacetaldehyde To a solution of 80 ml THF, 40 ml water, and 800 mg oxalic acid was added 9.6 g (40 mmol) of N-benzyloxycarbonyl aminoacetaldehyde dimethyl acetal, and refluxed for 4 days. The THF was removed under reduced pressure and the remaining solution was extracted with ether (3*100 ml), the ether fractions were combined and dried over anhydrous sodium sulfate. The ether was removed under reduced pressure and the remaining solution was purified by flash chromatography (hexane and ethyl acetate 3:1 then 1:1) to yield 3.88 g, 50% yield.
  • 6
  • [ 67561-03-9 ]
  • [ 1421-65-4 ]
  • [ 880262-98-6 ]
  • 7
  • [ 67561-03-9 ]
  • [ 63038-27-7 ]
  • C17H26N2O4 [ No CAS ]
  • 8
  • [ 67561-03-9 ]
  • [ 21950-36-7 ]
  • [ 1381760-60-6 ]
YieldReaction ConditionsOperation in experiment
44% With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane
28% Stage #1: N-benzyloxycarbonylglycinal; 5'-amino-5'-deoxy-2',3'-O-isopropylideneadenosine With acetic acid In methanol at 20℃; 4A MS; Stage #2: With sodium tetrahydroborate In methanol for 1h; 1 Step 1. To a solution of 9-((3aR,4R,6R,6aR)-6-(aminomethyl)-2,2- dimethyltetrahydrofuro[3,4-d][l,3]dioxol-4-yl)-9H-purin-6-amine (Townsend, A. P. et al Org. Let. 2009, 11, 2976-2979) (306 mg, 1 mmol) and benzyl (2-oxoethyl)carbamate (290 mg, 1.5 mmol) in MeOH (4 niL, dry) was added two drops of HOAc and 4A MS (10 mg), then the reaction mixture was stirred at room temperature overnight. NaBH4 (60 mg, 1.6 mmol) was added slowly, then stirred for another 1 h, quenched with NaHC03 (sat, aqueous, 5 mL), the mixture was extracted with DCM (10 mL x 3), dried over Na2S04 andconcentrated. The crude was purified by prep-TLC eluting with DCM: MeOH (10: 1) to afford the desired product 1 as a white solid (135 mg, 28 %). LC/MS (m/z): 483.9 [M+l]+.
  • 9
  • [ 77987-49-6 ]
  • [ 67561-03-9 ]
  • [ 1138-80-3 ]
YieldReaction ConditionsOperation in experiment
1: 44.7% 2: 17.8% With tert.-butylhydroperoxide; Caldariomyces fumago chloroperoxidase In aq. acetate buffer at 20 - 23℃; for 30h; Enzymatic reaction; 2.12.1. Reaction with soluble CPO General procedure: 5000 U of CPO were introduced in a 10 mL reaction medium containing 20 mM Cbz-ethanolamine and 100 mM acetate buffer at pH 5.0. The reaction started after addition of a 5-μL pulse of a solution containing 1.67 M of tert-butyl hydroperoxide. t-BuOOH pulses were added at a rate of 3 mM/h (18.02 × 10-6 L/h) using a single-syringe automatic microburette (Crison Instruments, Spain). Samples were taken periodically and analyzed by liquid chromatography in order to quantify Cbz-ethanolamine and Cbz-glycinal concentrations.
42% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; Trametes versicolor laccase; oxygen In ethyl acetate at 25℃; for 24h; Green chemistry; Enzymatic reaction; 2.9. N-Cbz-aminoethanol oxidation by laccase/O2/TEMPO system General procedure: Reactions were conducted in 15 mL glass pressure vials. N-Cbz-aminoethanol (10 mg, 0.05 mmol, 25 mM) and TEMPO (2.5 mg, 0.016 mmol, 8 mM) were dissolved in acetate buffer (2 mL, 50 mM, pH 4.5), acetate buffer (1 mL, 50 mM, pH 4.5)/CH2Cl2 (1 mL), acetate buffer (1 mL, 50 mM, pH 4.5)/hexane (1 mL) or acetate buffer (1 mL, 50 mM, pH 4.5)/AcOEt (1 mL). This solution was aerated during 5 min. Then, laccase (4 mg, 50 U) was added. The reaction was stirred in the presence of O2 (2 atm) at 25 °C. Samples (50 μL) were withdrawn at 1, 3, 5, 7, and 24 h, diluted with MeOH (950 μL) and subsequently analyzed by HPLC.
14% With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; Trametes versicolor laccase; oxygen In aq. acetate buffer at 25℃; for 24h; Green chemistry; Enzymatic reaction; 2.9. N-Cbz-aminoethanol oxidation by laccase/O2/TEMPO system General procedure: Reactions were conducted in 15 mL glass pressure vials. N-Cbz-aminoethanol (10 mg, 0.05 mmol, 25 mM) and TEMPO (2.5 mg, 0.016 mmol, 8 mM) were dissolved in acetate buffer (2 mL, 50 mM, pH 4.5), acetate buffer (1 mL, 50 mM, pH 4.5)/CH2Cl2 (1 mL), acetate buffer (1 mL, 50 mM, pH 4.5)/hexane (1 mL) or acetate buffer (1 mL, 50 mM, pH 4.5)/AcOEt (1 mL). This solution was aerated during 5 min. Then, laccase (4 mg, 50 U) was added. The reaction was stirred in the presence of O2 (2 atm) at 25 °C. Samples (50 μL) were withdrawn at 1, 3, 5, 7, and 24 h, diluted with MeOH (950 μL) and subsequently analyzed by HPLC.
  • 10
  • [ 67561-03-9 ]
  • [ 6331-09-5 ]
  • ethyl (R)-2-((2-(((benzyloxy)carbonyl)amino)ethyl)amino)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
42 g With sodium tris(acetoxy)borohydride; triethylamine; In methanol; dichloromethane; at 0 - 20℃; 36 g of <strong>[6331-09-5]D-alanine ethyl ester hydrochloride</strong> was dissolved in 200 mL of DCM.Add 25g of triethylamine to neutralize,The salt was removed by filtration.Collect the filtrate,40 g of N-Cbz-aminoacetaldehyde in 300 mL of methanol was added.Stir for 15min,Cool down to 0 C.Add 48g of triethylamine,87 g of sodium triacetoxyborohydride was added in portions.After the addition,Continue to stir,Slowly rise to room temperature,Stir overnight.The TLC monitors until the reaction is complete.The reaction system is quenched by adding a saturated sodium hydrogencarbonate solution.Liquid separation,The water layer was extracted once more with 200mLDCM.Combine the organic phase,Concentrate to give a clear liquid.Separation and purification by silica gel column chromatography (using n-heptane / ethyl acetate = 1/2 as eluent)42 g of a colorless viscous liquid were obtained.
  • 11
  • [ 67561-03-9 ]
  • [ 149-73-5 ]
  • [ 114790-39-5 ]
YieldReaction ConditionsOperation in experiment
With magnesium sulfate; toluene-4-sulfonic acid; In methanol; dichloromethane; at -78 - 20℃; General procedure: A solution of 4 (1.00 mmol) in dichloromethane (5 mL) and MeOH (5 mL) was cooled to -78 C using a dry ice/acetone bath. Then, ozone was bubbled through the reaction mixture for 10 min. After the ozonolysis was completed, the reaction mixture was quenched with dimethyl sulfide (0.5 mL, 6.5 mmol) at -78 C, and p-toluenesulfonic acid monohydrate (19 mg, 0.10 mmol), MgSO4 (1.0 g), and trimethyl orthoformate (3.0 mL) were added to the reaction mixture. The reaction mixture was allowed to warm up to room temperature, and stirred for overnight. Then, the reaction mixture was filtered and concentrated on a rotary evaporator under reduced pressure. The resulting crude oil was purified by silica gel column chromatography to afford 9 in 48-79% yields.
  • 12
  • [ 67561-03-9 ]
  • [ 2389-48-2 ]
  • methyl N<SUP>2</SUP>-(2-(((benzyloxy)carbonyl)amino)ethanethioyl)-N<SUP>6</SUP>-(tert-butoxycarbonyl)-L-lysinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With sulfur; sodiumsulfide nonahydrate; copper dichloride In tetrahydrofuran at 50℃; for 10h; Schlenk technique;
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