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Chemical Structure| 131372-64-0 Chemical Structure| 131372-64-0

Structure of 131372-64-0

Chemical Structure| 131372-64-0

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Product Details of [ 131372-64-0 ]

CAS No. :131372-64-0
Formula : C8H16O5S
M.W : 224.27
SMILES Code : CS(=O)(OCC1COC(C)(C)OC1)=O

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Application In Synthesis of [ 131372-64-0 ]

* 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 [ 131372-64-0 ]

[ 131372-64-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 4728-12-5 ]
  • [ 124-63-0 ]
  • [ 131372-64-0 ]
YieldReaction ConditionsOperation in experiment
99% With triethylamine; In dichloromethane;Cooling with ice; To dichloromethane solution (100 ml) of 14 (6.38 g, 43.64 mmol), triethylamine (9.08 ml, 65.47 mmol) was added, and methane sulfonyl chloride (3.69 ml, 48.01 mmol) was dropped while cooling in ice with shaking, and stirred for 30 min at the same temperature. The reaction mixture was added cold water, and extracted with ethyl acetate. The extract was washed with water, dried, and evaporated to dryness under reduced pressure, and the residue was purified by silica gel column chromatography (solvent: ethyl acetate/n-hexane = 1/2), to obtain 15 (9.66 g, 99percent) of oily light yellow substance. APCI-MS m/z 225[M+H]+
97.8% With triethylamine; In dichloromethane;Cooling with ice; (2,2-Dimethyl-1,3-dioxan-5-yl)methanol (1.0 g, 6.84 mmol) was dissolved in CH2C12 (30 mL) and cooled in ice bath. Triethylamine (1.14 mL, 8.21 mmol) was added, followed by methanesulfonyl chloride (0.586 mL, 7.52 mmol) and the reaction mixture was warmed to room temperature. The reaction mixture was washed with 0.1 N HCI, saturated aqueous NaHCO3, and the combined organic extracts were dried over sodium sulfate, filtered and concentrated to afford (2,2-dimethyl- 1 ,3-dioxan-5-yl)methyl methanesulfonate (1.5 g, 6.69 mmol, 97.8 percent yield) as a clear colorless oil.
95% With triethylamine; In dichloromethane; at 20℃; for 2h;Cooling; Methanesulfonic acid 2 ,2-dimethyl- [ 1 ,3] dioxan-5-ylmethyl ester[0684] MsCl (4.4 mL, 56 mmol) was added slowly to a solution OfEt3N (9.8 mL, 71 mmol) and (2,2-dimethyl-[l,3]dioxan-5-yl)-methanol (6.87 g, 47.0 mmol) in CH2Cl2 (100 mL) at 0 0C (bath temp). The reaction mixture was stirred at rt for 2 h and then quenched with H2O (100 mL). The mixture was extracted with CH2Cl2 and <n="213"/>the organic fractions were dried (MgSO4) and concentrated in vacuo to give the title compound as a colorless liquid: yield 10.02 g (95percent).[0685] 1H NMR (400 MHz, CDCl3) delta (ppm): 4.42 (d, J= 7.4 Hz, 2H), 4.13-4.04 (m, 2H), 3.82-3.74 (m, 2H), 3.05 (s, 3H), 2.05-1.95 (m, IH), 1.46 (s, 3H), 1.40 (s, 3H).
92% With triethylamine; In dichloromethane; at -20℃; for 1h; 10303] 2,2-Dimethyl-5-(hydroxymethyl)- 1 ,3-dioxane (3a) (5.00 g) was dissolved in 67 mE of CH2C12, and 5.42 mE of triethylamine was added thereto, followed by cooling to?20° C. Further, 2.56 mE of mesyl chloride (MsC1) was added, and the resulting mixture was stirred at ?20° C. for 1 hout Thereafter, 50 mE of water was added to the reaction mixture to stop the reaction, and extraction was performed twice with 40 mE of CH2C12. After the separated organic layers were washed with water, CH2C12 was distilled offunder reduced pressure, and the resulting residue was purifled with silica gel chromatography (n-hexane:ethylacetate=i :1) to obtain 6.22 g of compound (4a) (yield: 92percent).10304] ?H-NMR (500 MHz, CDC13):10305] oe: 1.39 (s, 3H), 1.46 (s, 3H), 2.00 (m, 1H), 3.04 (s,3H), 3.78 (dd, 2H, J=12, 3 Hz), 4.08 (dd, 2H, J=ii.5, 2.5 Hz), 4.42 (d, 2H, J=7 Hz)
91% With triethylamine; In dichloromethane; at 20℃; for 3h; To a 500 mL round bottomed flask equipped with a magnetic stir bar containing DCM (200 mL) was placed 87 (5 g, 34 mmol, 1 equiv). To this solution was added mesyl chloride (4.3 <n="86"/>g, 38 mmol, 1.1 equiv), Et3N (5 g, 51 mmol, 1.5 equiv) and the reaction was allowed to stir at room temperature for 3 h. The reaction was then poured into water (100 mL) and extracted into DCM (3 x 100 mL). The combined organic extracts were washed with brine (100 mL), NaHCO3 solution (100 mL), dried (Na2SO4) and concentrated in vacuo. The residue was purified over silica gel. Product eluted out in 50percent EtOAc:Hexanes mixture in a gradient elution on a Combiflash purification system. Isolated 87 (7 g, 91percent) as a colorless solid. MS: [M+H]+: 225.
84% With triethylamine; In dichloromethane; at 0 - 20℃; for 16h; [00652] Step B: Preparation of (2,2-dimethyl-1.3-dioxan-5-yl)methyl methanesulfonate: To a solution of (2,2-dimethyl-l,3-dioxan-5-yl)methanol (1.0 g, 6.84 mmol) in DCM (30 mL) at 0 °C was added triethylamine (1.43 mL, 10.3 mmol) followed by mesyl chloride (0.58 mL, 7.52 mmol). The mixture was allowed to warm slowly to ambient temperature over 16 hours then partitioned between 0.5 M HC1 (40 mL) and DCM (20 mL). The aqueous layer was extracted with DCM (2 x 20 mL) and the combined organic phases were washed with brine (20 mL), dried over Na2S04, filtered and concentrated (2,2-dimethyl-l ,3-dioxan-5-yl)methyl methanesulfonate (1.29 g, 84percent yield) as a colorless oil. ]H NMR (CDC13) delta 4.41 (d, J = 7.3 Hz, 2H), 4.08 (dd, J = 12.5, 3.6 Hz, 2H), 3.77 (dd, J = 12.5, 3.9 Hz, 2H), 3.04 (s, 3H), 2.03- 1.98 (m, 1H), 1.46 (s, 3H), 1.39 (s, 3H) ppm.
With triethylamine; In dichloromethane; at 0 - 20℃; Methanesulfonyl chloride(0.97 mL, 12.40 mmol) was added dropwise to a stirred solution of (2,2-dimethyl-1,3-dioxan-5-yl)methanol57 (18, 1.51 g, 10.33 mmol) and Et3N (2.18 mL, 15.49 mmol) in CH2Cl2 (10 mL) at 0 oC. The mixture was warmed to rt and stirred for 30 min then diluted with CH2Cl2 (20 mL) and washed with aq. NaHCO3 (sat., 3 x 10 mL) then dried and the solvent evaporated to give the crude mesylate as an oil. The latter was dissolved in DMF (7 mL),sodium thiomethoxide (1.45 g, 20.66 mmol) added and the mixture stirred at rt for 16 h. Diethyl ether (100 mL) was added and the solution washed with H2O (4 x 15 mL), brine (15 mL), dried and the solvent evaporated. The residue was chromatographed (EtOAc-hexanes,5:95) to give 19 as a colourless oil (1.38 g, 76percent).
With triethylamine; In dichloromethane; at -78 - 0℃; for 3h; (2,2-Dimethyl-1,3- dioxan-5-yl)methanol (50 mg, 0.34 mmol) was dissolved in DCM (0.4mL). The mixture was cooled in to -78oC. Triethylamine (143 muL, 1mmol) and methanesulfonyl chloride (32 muL, 0.4 mmol) were added sequentially. The reaction mixture stirred at -78 ^C -> 0 ^C. After 3 hours, the reaction mixture was transferred to a separatory funnel, diluted with DCM, and washed with sodium bicarbonate. The organic layer was dried over sodium sulfate, filtered, and concentrated.1H NMR (600 MHz, Acetone-d6) ^ ppm 1.35 (d, J = 2.5 Hz, 3H) 1.42 (d, J = 2.9 Hz, 3H) 2.03 (td, J=7.2, 3.3 Hz, 1 H) 3.14 (d, J = 3.3 Hz, 3H) 3.74 - 3.83 (m, 2H) 4.04 - 4.15 (m, 2H) 4.39 (dd, J=7.2, 3.1 Hz, 2H);

 

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