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Chemical Structure| 6919-98-8 Chemical Structure| 6919-98-8

Structure of 6919-98-8

Chemical Structure| 6919-98-8

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Product Details of [ 6919-98-8 ]

CAS No. :6919-98-8
Formula : C13H17BrO9
M.W : 397.17
SMILES Code : O=C([C@@H]1[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](Br)O1)OC
MDL No. :MFCD30489050

Safety of [ 6919-98-8 ]

Application In Synthesis of [ 6919-98-8 ]

* 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 [ 6919-98-8 ]

[ 6919-98-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 6919-98-8 ]
  • [ 17924-92-4 ]
  • [ 1416776-57-2 ]
YieldReaction ConditionsOperation in experiment
74% To a solution of 1-bromo-1-deoxy-2,3,4-tri-O-acetyl-beta,D-glucuronic acid methyl ester (7) (99.3 mg, 0.25 mmol) and ZEN (31.8 mg, 0.1 mmol) in dry acetonitrile (2 mL) powdered molecular sieves (3 A, 100 mg) were added. The reaction mixture was stirred for 3 h at room temperature. Ag2O (34.8 mg, 0.15 mmol) was added and stirring was continued in the dark for 24 h. After further addition of 7 (99.3 mg, 0.25 mmol) and Ag2O (34.8 mg, 0.15 mmol), reaction control via TLC indicated full consumption of ZEN after 24-36 h. The reaction mixture was diluted with dichloromethane, filtered through celite, concentrated and subjected to column chromatography (hexanes/EtOAc, gradient elution from 8/1 to 1/1) to yield 8 (47.0 mg, 74%) as a white solid: 1H NMR (acetone-d6): delta 11.85 (s, 1H, OH), 7.05 (d, 1H, J11,12 15.4 Hz, H-12), 6.65 (d, 1H, J13,15 2.4 Hz, H-13), 6.57 (d, 1H, H-15), 5.82 (ddd, 1H, J10a,11 10.3, J10b,11 4.5 Hz, H-11), 5.75 (d, 1H, J1?,2? 7.9 Hz, H-1?), 5.48 (t, 1H, J2?,3? 9.6, J3?,4? 9.6 Hz, H-3?), 5.26 (t, 1H, J4?,5? 9.7 Hz, H-4?), 5.25 (dd, 1H, H-2?), 5.05 (sext, 1H, J3,4 5.9, J3,Me 5.9 Hz, H-3), 4.70 (d, 1H, H-5?), 3.72 (s, 3H, OCH3), 2.87-2.76 (m, 1H, H-8a), 2.66-2.58 (m, 1H, H-6a), 2.37-2.04 (m, 5H, H-6b, H-8b, H-9a, H-10a, H-10b), 2.04 (s, 3H, COCH3), 2.02 (s, 3H, COCH3), 2.01 (s, 3H, COCH3), 1.85-1.75 (m, 2H, 2 H-5), 1.70-1.65 (m, 2H, 2 H-4), 1.62-1.50 (m, 1H, H-9b), 1.41(d, 3H, CH3); 13C NMR (acetone-d6): delta 209.4 (s, 1C, C-7), 171.0 (s, 1C, C-1), 169.3 (s, 1C, COCH3), 169.0 (s, 1C, COCH3), 168.8 (s, 1C, COCH3), 166.8 (s, 1C, C-6?), 164.7 (s, 1C, C-16), 160.7 (s, 1C, C-14), 143.5 (s, 1C, C-12a), 133.3 (d, 1C, C-11), 132.3 (d, 1C, C-12), 108.6 (d, 1C, C-13), 106.0 (s, 1C, C-16a), 102.6 (d, 1C, C-15), 97.0 (d, 1C, C-1?), 73.9 (d, 1C, C-3), 72.0 (d, 1C, C-5?), 71.6 (d, 1C, C-3?), 70.7 (d, 1C, C-2?), 69.2 (d, 1C, C-4?), 52.1 (q, 1C, OCH3), 42.5 (t, 1C, C-6), 36.0 (t, 1C, C-8), 34.5 (t, 1C, C-4), 30.9 (t, 1C, C-10), 21.9 (t, 1C, C-5), 20.8 (t, 1C, C-9), 19.8 (q, 1C, CH3), 19.6 (q, 1C, COCH3), 19.6 (q, 1C, COCH3), 19.5 (q, 1C, COCH3); ESI-MS: m/z 657 [M+Na]+; HRMS: m/z calcd for C31H38O14Na [M+Na]+: 657.2154. Found: 657.2171.
  • 2
  • [ 6919-98-8 ]
  • [ 22532-60-1 ]
  • (2S,3R,4S,5S,6S)-2-(3-bromo-4-formylphenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With silver(l) oxide; In acetonitrile; at 20℃; for 3h;Darkness; A mixture of (3R,4S,5S,6S)-2-bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (2.67 g), <strong>[22532-60-1]2-bromo-4-hydroxybenzaldehyde</strong> (0.90 g) and silver oxide (1.56 g) was stirred in acetonitrile (20 mL) at room temperature protected from light. After 3 hours, the reaction was diluted with dichloromethane (20 mL), filtered through diatomaceous earth, washed with additional dichloromethane (40 mL) and concentrated. The residue was purified by silica gel chromatography, eluting with a gradient of 5percent to 50percent hexanes/ethyl acetate over 30 minutes, to provide the title compound. MS (ESI) m/e 517.1 (M+H)+.
  • 3
  • [ 6919-98-8 ]
  • [ 38170-02-4 ]
  • (2S,3R,4S,5S,6S)-2-(2-formyl-5-iodophenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With silver(l) oxide; In acetonitrile; at 20℃;Darkness; To a stirred solution of <strong>[38170-02-4]2-hydroxy-4-iodobenzaldehyde</strong> (0.95 g) in acetonitrile (10 ml) was added (3R,4S,5S,6S)-2-bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (2.5 g) and silver oxide (2 g). The mixture was covered with aluminum foil and was stirred at room temperature overnight. After filtration through diatomaceous earth, the filtrate was washed with ethyl acetate, the solution was concentrated. The reaction mixture was purified by flash chromatography using an ISCO CombiFlash system, SF40-80g column, eluted with 15-30% ethyl acetate/heptane (flow rate : 60ml/min), to provide the title compound.
 

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