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Chemical Structure| 104873-15-6 Chemical Structure| 104873-15-6

Structure of 104873-15-6

Chemical Structure| 104873-15-6

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Product Details of [ 104873-15-6 ]

CAS No. :104873-15-6
Formula : C17H18N2O7
M.W : 362.33
SMILES Code : [H][C@]1([C@](C(N12)=O)([C@@H](C)O)[H])[C@@H](C)C(C2C(OCC3=CC=C(N(=O)=O)C=C3)=O)=O
MDL No. :N/A

Safety of [ 104873-15-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H373
Precautionary Statements:P260-P264-P270-P301+P312+P330-P314-P501

Application In Synthesis of [ 104873-15-6 ]

* 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 [ 104873-15-6 ]

[ 104873-15-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 104873-15-6 ]
  • [ 96034-64-9 ]
  • [ 96036-02-1 ]
YieldReaction ConditionsOperation in experiment
Example 1 ] Synthesis of (4R,5S,6S)- 4-Nitrobenzyl-3-[[(3S,5S)-5-[(dimethylamino)carbonyl]-l-[[(4-nitrobenzyl)oxy]carbonyl]-3-pyrr olidinyl]thio] -6- [( 1 R)- 1 -hydroxyethyl] -4-methyl-7-oxo- 1 -azabicyclo[3 ,2,0]hept-2-ene-2-carboxyl ate(XXTV). diazo-ketone ester [(IX). 4Og, 0.102mol] and ethyl acetate (200 ml) were added to a flask equipped with returning current condenser. The mixture was heated to 600C, and rhodium octanoate (140 mg) was added. The mixture were strongly stirred for 30 min at the same temperature until the diazo-ketone ester reacted completely. The solution of 4- beta -methyl azadicycloketo ester(X) was obtained. The reaction solution was used in the next step without separation.To the above solution of 4- beta -methyl azadicycloketo ester (X) was added acetonitrile (dry, 300 ml) and the mixture was cooled to -10 - -150C in ice-salt bath. Diisopropylethanamine (14.57g, O.lBmol) and diphenyl chlorophosphonate (27.54g, 0.102mol) was then added. The mixture were stirred for 5 h at the same temperature until the 4- beta -methyl azadicycloketo ester (X) reacted completely. Then,[2S,4S]-l-p-nitrobenzyloxycarbonyl-2-dimethylaminocarbonyl-4-thiolpyrrolidne (XX) (34g, 0.096 mol) and diisopropylethamine (15.4g, 0.133mol) were added at the same temperature and the mixture was stirred for 5-8 h. After completion of the reaction, the reaction solution was diluted by ethyl acetate (500 ml) and washed with aqueous sodium phosphate monobasic solution. The organic phase was dried with anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The resulting residue (75 g, quantified by HPLC containing 60 g of targeted compound, 84% yield) may be either directly used in the next step, or be crystallized as following: 250 ml ethyl acetate and then seed crystal was added and stirred at 10-15 C for 3-5 h, then substantive crystals were precipitated, and the crystals were collected by filtration and dried, to obtain crystalline (4R,5S,6S)-4-Nitrobenzyl-3 - [[(3 S ,5 S)-5- [(dimethylamino)carbonyl] - 1 - [[(4-nitrobenzyl)oxy] carbonyl] -3 -pyrr olidinyl]thio]-6-[(lR)-l-hydroxyethyl]-4-methyl-7-oxo-l-azabicyclo[3,2,0]hept-2-ene-2-carboxyl <n="16"/>ate (XXTV) (53.4g, yield 75%).The physical data of compound (XXTV):Rmax"eat (cm 1): 1780, 1745, 1705, 1650, 1605, 1515, 1342, 1257.NMR 5 (CDCl3): 1.49(3H, d, J=6 Hz), 2.99(3H, s), 3.11(3H, s), 5.25(4H, s), 5.23 ^P 5.46(2H, ABq, J=14 Hz), 7.53(4H, d, J=8.5 Hz), 7.62(2H, d, J=8.5 Hz), 8.18(6H, d, J=8.5 Hz).[ alpha ]z)28 + 7.7 (c=0.303, acetone)
 

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