(1R,2S,5R)-(-)-MENTHYL(S)-P-TOLUENESULFINATE
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(1R,2S,5R)-(-)-MENTHYL(S)-P-TOLUENESULFINATE
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CAS No:
1517-82-4
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Formula:
C17H26O2S
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Chemical Name:
(1R,2S,5R)-(-)-MENTHYL(S)-P-TOLUENESULFINATE
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Synonyms:
menthylp-toluenesulfinate;(S)-(-)-MENTHYLP-TOLUENESULFINATE;Menthyl(S)-4-methylbenzenesulfinate;(?-(1R)-Menthyl(S)-p-toluenesulfinate;(-)-(1R)-MENTHYL(S)-TOLUENE-4-SULFINATE;(-)-Menthyl(S)-4-methylbenzenesulfinate;(1R,2S,5R)-MENTHYL(S)-P-TOLUENESULFINATE;(1R,2S,5R)-(-)-MENTHYL(S)-P-TOLUENESULFINATE;(S)-(-)-P-TOLUENESULFINICACIDL-MENTHYLESTER;p-Toluenesulfinicacid(1R,3R,4S)-menthylester
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CAS No:
(1R,2S,5R)-(-)-MENTHYL(S)-P-TOLUENESULFINATE Use and Manufacturing
General procedure: To a 250 mL flame-dried NGeneral procedure: In a test tube containing the appropriate sodium salt of sulfinic acid, 1a-d (1 mmol) was added the appropriate alcohol (1 mL) followed by dichloromethane (4 mL) [For more complex alcohols, 3 equiv. (3 mmol) of alcohol were used]. Under stirring, sulfuric acid (106 mL, 2 equiv.) was added and after 30 min of reaction, powdered 4 Å molecular sieves (200 mg) was added. The mixture was stirred for the time indicated on Table 2 and then diluted with dichloromethane (10 mL) and transferred to a separation funnel. The organic phase was then washed with water (2 x 20 mL), dried over anhydrous MgSO4 and filtered through a pad of silica. The solvents were removed in vacuo and the resulting crude product was further purified by flash column chromatography [hexanes:EtOAc (98:2)].General procedure: In a flame-dried, nitrogen purged 100 mL round-bottom flask equipped with magnetic stir bar at room temperature were placed anhydrous toluene sulfinic acid (0.72 g, 4.05 mmol), methylene chloride (12 mL), and pivaloyl chloride (0.49 mL, 4.00 mmol). The resulting mixture was allowed to stir for 5 hours. After the allocated time, triethylamine (0.67 mL, 4.8 mmol) and the alcohol substrate were added. The resulting mixture was allowed to sit overnight and quenched the following day. The mixture was extracted with dichloromethane and 1M HCl. The combined organic layers were washed with brine and dried over anhydrous MgSO
Computed Properties
Molecular Weight:294.5
XLogP3:5.3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:294.16535124
Monoisotopic Mass:294.16535124
Topological Polar Surface Area:45.5
Heavy Atom Count:20
Complexity:321
Defined Atom Stereocenter Count:3
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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(1R,2S,5R)-(-)-MENTHYL(S)-P-TOLUENESULFINATE
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