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Chemical Structure| 133153-76-1 Chemical Structure| 133153-76-1

Structure of 133153-76-1

Chemical Structure| 133153-76-1

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Product Details of [ 133153-76-1 ]

CAS No. :133153-76-1
Formula : C9H17NO5
M.W : 219.24
SMILES Code : COC([C@H](CNC(OC(C)(C)C)=O)O)=O
MDL No. :MFCD30075813
InChI Key :DQTVOWNRRLNDEY-LURJTMIESA-N
Pubchem ID :18652472

Safety of [ 133153-76-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 133153-76-1 ]

* 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 [ 133153-76-1 ]

[ 133153-76-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 133153-76-1 ]
  • [ 59237-53-5 ]
  • (S)-methyl 6-((3-((tert-butoxycarbonyl)amino)-1-methoxy-1-oxopropan-2-yl)oxy)-5-nitronicotinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 - 20℃; for 1h;Inert atmosphere; Molecular sieve; Part III - Synthesis of (S)-methyl 6-((3-((terf-butoxycarbonyl)amino)-l-methoxy-l- oxopropan-2-yl)oxy)-5-nitronicotinate [0263] To (iS)-methyl 3-((fert-butoxycarbonyl)amino)-2-hydroxypropanoate (0.78 g, 3.6 mmol) and <strong>[59237-53-5]methyl 6-chloro-5-nitro-pyridine-3-carboxylate</strong> (0.77 g, 3.6 mmol) in anhydrous tetrahydrofuran (15 mL) under nitrogen with activated 4A molecular sieves at 0°C was added l ,8-diazabicyclo[5.4.0]undec-7-ene (0.69 mL, 4.6 mmol). Then, the cooling bath was removed from the reaction container and the reaction mixture was stirred at ambient temperature for 1 hour. A solid was observed to precipitate out of the solution. The reaction mixture was diluted with ethyl acetate (15 mL), solids were removed by filtration, and the filtrates were concentrated in the presence of silica to provide a crude product that was purified by column chromatography eluting with a gradient of 5-50percent ethyl acetate in hexanes to provide the title compound. (0.98 g, 69percent> yield
  • 2
  • [ 52558-24-4 ]
  • [ 74-88-4 ]
  • [ 133153-76-1 ]
YieldReaction ConditionsOperation in experiment
47% Part II- Synthesis of (S)-methyl3-((tert-butoxycarbonyl)amino)-2-hydroxypropanoate [0262] To <strong>[52558-24-4](S)-3-((tert-butoxycarbonyl)amino )-2-hydroxypropanoic acid</strong> (1.57 g, 7.65 mmol)in N,N-dimethylformamide (15 mL) was added sodium bicarbonate (1.3 g, 15.3 mmol),5 followed by addition ofiodomethane (0.57 mL, 9.2 mmol). The resulting mixture was stirredat ambient temperature for 6 hours. Then, another 0.2 mL of iodomethane was added, andthe reaction mixture was stirred at ambient temperature overnight. Next, the reaction mixturewas diluted with ethyl acetate, washed with saturated sodium bicarbonate, washed with brine,dried with sodium sulfate, filtered, and concentrated in vacuo to yield title compound. (0.7810 g, 47% yield).
  • 3
  • [ 67-56-1 ]
  • [ 52558-24-4 ]
  • [ 133153-76-1 ]
YieldReaction ConditionsOperation in experiment
98% With diazomethyl-trimethyl-silane; In hexane; dichloromethane; at 0 - 20℃; for 0.5h; (2S)-3-(tert-Butoxycarbonylamino)-2-hydroxy-propionic acid 15b (35 g, 0.17 mol) was dissolved in dichloromethane (50 mL)In a mixed solvent with methanol (50 mL),Cool down to 0 C,A solution of trimethylsilyldiazomethane in n-hexane (100 mL, 0.20 mol, 2 mol/L) was added dropwise.The reaction was carried out for 30 minutes at room temperature.Concentrated under reduced pressure,The title compound 15c was obtained as a colorless oil (37 g, yield 98%).
 

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