57820-69-6|(3R,4S,5S,6S)-2-bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate| Ambeed

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CAS No. :	57820-69-6
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(Br)O1)OC
MDL No. :	N/A

Yield	Reaction Conditions	Operation in experiment
	With silver(l) oxide; In acetonitrile; at 20℃;Darkness;	[0001127] 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. MS (ESI) m/e 586.9 (M+Na)+.
	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) was10 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 roomtemperature overnight. After filtration through diatomaceous earth, the filtrate was washed with ethylacetate, the solution was concentrated. The reaction mixture was purified by flash chromatographyusing an ISCO CombiFlash system, SF40-80g column, eluted with 15-30% ethyl acetate/heptane15 (flow rate : 60ml/min), to provide the title compound. MS (ESI) m/e 586.9 (M+Nat
	With iodine; silver(l) oxide; In acetonitrile; at 20℃; for 4h;	To a stirred solution of (3R,4S,5S,6S)-2-bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3 ,4,5-triyl triacetate (1.0 g) in acetonitrile (12 niL) was added <strong>[38170-02-4]2-hydroxy-4-iodobenzaldehyde</strong> (0.999 g), 12(0.192 g) and silver oxide (2.001 g). The mixture was covered with aluminum foil and stirred at room temperature for 4 hours. The reaction was filtered through Celite and washed with ethyl acetate. The solvent was removed. The residue was purified by silica gel chromatography, eluting with 10%-25% petroleum ether/ethyl acetate, to give the tide compound. 1H-NMR (CDC13, 400 MHz):2.07 (s, 9H), 3.76 (s, 3H), 4.26-4.28 (m, 1H), 5.25-5.27 (m, 1H), 5.34-5.40 (m, 3H), 7.5 1-7.59 (m, 3H), 10.28 (s, 1H). MS (ESI) m/z 587 (M+Na).

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H200	Unstable explosive
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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H371	May cause damage to organs
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H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 57820-69-6

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CAS No.: 57820-69-6

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[ 57820-69-6 ] Synthesis Path-Downstream 1~3

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