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CAS No. : | 791616-63-2 | MDL No. : | MFCD10567009 |
Formula : | C50H57O4P | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AGQAQYPGJDBIQR-UHFFFAOYSA-N |
M.W : | 752.96 | Pubchem ID : | 11498681 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
99% | Stage #1: (Ra)-3,3’-bis(2,4,6-triisopropylphenyl)-[1,1’-binaphthalene]-2,2’-diol With pyridine; trichlorophosphate for 14h; Inert atmosphere; Reflux; Stage #2: With lithium hydroxide monohydrate at 20℃; Reflux; Inert atmosphere; | |
78% | Stage #1: (Ra)-3,3’-bis(2,4,6-triisopropylphenyl)-[1,1’-binaphthalene]-2,2’-diol With pyridine; trichlorophosphate at 0 - 20℃; for 3h; Inert atmosphere; Stage #2: With lithium hydroxide monohydrate at 0 - 20℃; for 1h; | Synthesis of 8a-8k General procedure: To a solution of a compound 6a-6k (1 equiv.) in pyridine (8 vol) was added POCl3 (2 equiv.) dropwise under the nitrogen atmosphere at 0 °C. The reaction mixture was warmed up to room temperature and stirred for 3 h (monitored by TLC). Then the mixture was cooled down to ca 5 °C and H2O (10 equiv.) was added to it and stirred at RT for 1 h (TLC). Pyridine was removed under vacuum, and the residue was refluxed in 6N HCl (20 vol.) overnight. The solid was filtered off and washed with water until the last drop showed pH 5-6. The solid was further recrystallized to afford the corresponding pure product. |
Multi-step reaction with 2 steps 1: 4-dimethylaminopyridine; triethylamine; trichlorophosphate / dichloromethane / 2.17 h / 0 - 20 °C / Inert atmosphere 2: lithium hydroxide monohydrate; propanenitrile / dichloromethane / 12 h / 98 °C / Inert atmosphere |
Multi-step reaction with 2 steps 1: triethylamine; trichlorophosphate / dichloromethane / 16 h / 20 °C / Inert atmosphere; Reflux 2: pyridine / lithium hydroxide monohydrate / 3 h / 100 °C / Inert atmosphere | ||
With pyridine; trichlorophosphate at 0 - 20℃; | ||
Multi-step reaction with 2 steps 1: trichlorophosphate; triethylamine / dichloromethane / 16 h / Inert atmosphere; Reflux 2: pyridine; lithium hydroxide monohydrate / lithium hydroxide monohydrate / 3 h / Inert atmosphere; Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: water; boron tribromide / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 2: triethylamine; trichlorophosphate / dichloromethane / 16 h / 20 °C / Inert atmosphere; Reflux 3: pyridine / water / 3 h / 100 °C / Inert atmosphere | ||
Multi-step reaction with 3 steps 1: boron tribromide / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 2: trichlorophosphate / pyridine / 14 h / Reflux; Inert atmosphere 3: water / 3 h / Reflux; Inert atmosphere | ||
Multi-step reaction with 2 steps 1.1: boron tribromide / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 2.1: triethylamine; trichlorophosphate; dmap / dichloromethane / 1 h / Inert atmosphere 2.2: 12 h / 100 °C / Inert atmosphere |
Multi-step reaction with 2 steps 1: boron tribromide / dichloromethane / 48 h / 0 - 20 °C / Inert atmosphere 2: pyridine; trichlorophosphate / 0 - 20 °C | ||
Multi-step reaction with 3 steps 1: boron tribromide / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 2: trichlorophosphate; triethylamine / dichloromethane / 16 h / Inert atmosphere; Reflux 3: pyridine; water / water / 3 h / Inert atmosphere; Reflux | ||
Stage #1: (Ra)-2,2’-dimethoxy-3,3’-bis(2,4,6-triisopropylphenyl)-1,1’-binaphthalene With boron tribromide In dichloromethane at 20℃; for 4h; Inert atmosphere; Stage #2: With pyridine; trichlorophosphate In dichloromethane at 70℃; for 3h; Inert atmosphere; | General Procedure for the Synthesis of chiral phosphates (1a-e). General procedure: The crude product 7 was dissolved in dry CH2Cl2 (20 mL) in 50 mL dry round bottom flask andcooled to 0, BBr3(10 mL, 10 mmol) was added slowly and the mixture subsequently stirred for4h at room temperature. When the reaction was completely checked by TLC, the mixture wascooled to 0 and water (20 mL) was added to quench the reaction. After extraction with CH2Cl2(3 × 30 mL), the organic phases were dried with anhydrous Na2SO4 and concentrated under areduced pressure, and the residue was purified by column chromatography on silica gel. Finally,the purified product (2 mmol, 1 equiv) was weighed in 50 mL dry round bottom flask, andpyridine (15 mL) and POCl3 (6 mmol, 3 equiv) were added at room temperature. The mixturesubsequently stirred for 3h at 70. When the reaction was completely checked by TLC, themixture was cooled to the room temperature, water (10mL) was added and stirred for 2h. Then 6NHCl (10 mL) was added. After extraction with CH2Cl2 (3 × 50 mL) and Saturated sodium chloride(25 mL), the organic phases were dried with anhydrous Na2SO4 and concentrated under a reducedpressure, and the residue was purified by column chromatography on silica gel to give thecatalysts 1a-e. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Stage #1: (Ra)-3,3’-bis(2,4,6-triisopropylphenyl)-[1,1’-binaphthalene]-2,2’-diol With dmap; triethylamine; trichlorophosphate In dichloromethane for 1h; Inert atmosphere; Stage #2: Trifluoromethanesulfonamide In dichloromethane at 100℃; for 12h; Inert atmosphere; |
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