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CAS No. : | 74808-09-6 | MDL No. : | MFCD03427010 |
Formula : | C36H36Cl3NO6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LMICALCPRSCSMO-BGSSSCFASA-N |
M.W : | 685.03 | Pubchem ID : | 11061437 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In dichloromethane; at 20℃; for 1.5h;Inert atmosphere;Kinetics; | General procedure: To a 10-mL, single-necked, round-bottomed flask fitted with a magnetic stir-bar, a nitrogen inletadapter and with a rubber septum was added diastereomerically pure 2,3,4,6-tetra-O-benzylglucosyltrichloroacetimidate 1 (alpha to yield beta product or to yield alpha product, 50 mg, 0.073 mmol)as a waxy glass followed by dry CH2Cl2 (0.75 mL, 0.03 M). The resultant suspension was stirredvigorously until it was a homogeneous, clear, colorless solution (ca. 30 min). To the resultantsolution was added carboxylic acid (0.077 mmol, 1.05 equiv) as a solid in a single portion. Theresulting clear solution was stirred at room temperature and monitored by TLC (20%EtOAc/Hexanes), then concentrated by rotary evaporation (15 mm Hg, 20-25 oC) after thereaction was judged to be complete. To the crude material (waxy glass) was added CH2Cl2 (5mL). After a further 30 min of stirring the solution was concentrated again by rotary evaporation(15 mm Hg, 20-25 oC). The resultant mucilaginous suspension was purified by flashchromatography on silica as follows; the crude material was loaded onto a pre-packed (2 x 8 cm,Si-gel, EtOAc/Hexanes (2/98) slurry, 15 psi) column as a suspension (CHCl3/Hexanes, 1/1, 2-3mL), rinsing with EtOAc/Hexanes (2/98). The column was then run with a gradient of increasingpolarity (EtOAc/Hexanes), as indicated in the individual procedures at no more than 5 psi. Thediastereomerically pure fractions were combined and triturated to a fine powder with hexanes. |
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