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[ CAS No. 477781-69-4 ]

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2D
Chemical Structure| 477781-69-4
Chemical Structure| 477781-69-4
Structure of 477781-69-4 *Storage: {[proInfo.prStorage]}

Quality Control of [ 477781-69-4 ]

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SDS

Product Details of [ 477781-69-4 ]

CAS No. :477781-69-4MDL No. :N/A
Formula : C16H26O7S Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :362.44Pubchem ID :24180090
Synonyms :

Computed Properties of [ 477781-69-4 ]

TPSA : 88.7 H-Bond Acceptor Count : 7
XLogP3 : 0.6 H-Bond Donor Count : 0
SP3 : 0.63 Rotatable Bond Count : 15

Safety of [ 477781-69-4 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 477781-69-4 ]

  • Upstream synthesis route of [ 477781-69-4 ]

[ 477781-69-4 ] Synthesis Path-Upstream   1~5

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YieldReaction ConditionsOperation in experiment
98% With triethylamine In dichloromethane at 0 - 20℃; To a stirred mixture of 7' (45.1 g, 159 mmol) and triethylamine (62.2 g, 636 mmol) in dichloromethane (800 mL) at 0 0C was added methanesulfonyl chloride (36.4 g, 318 mmol). After the addition, the reaction mixture was stirred overnight at room temperature. The reaction mixture was quenched with IN HCl (300 mL), extracted with ethyl acetate. The combined organic phase was dried over magnesium sulfate, concentrated to dryness and flash chromatography to afford compound 8' (56.2 g, 98percent) as clear oil. b. METHANESULFONATE 8'[00311] To a stirred solution of alcohol 7' (69.3 g, 243.7 mmol) and triethylamine(49.2 g, 68.4 mL, 487.0 mmol) in CH2Cl2 (700 mL) at 0 0C was added methanesulfonyl chloride (41.9 g, 28.3 mL, 365.6 mmol). The resulted mixture was stirred at rt. overnight and quenched with water (400 mL). Organic phase was collected and the aqueous phase was extracted with ethyl acetate. The combined organic phase was washed with 2N HCl (100 mL), brine (100 mL) and dried over anhydrous magnesium sulfate. Concentrated the solution under vacuum gave the methanesulfonate 8' as clear oil (86.6 g, 98percent). 1H NMR (400 MHz, CD3Cl3) δ 7.25-7.32 (m, 5H), 4.54 (s, 2H), 4.32-4.34 (m, 2H), 3.71-3.73 (m, 2H), 3.59-3.66 (m, 12H), 3.03 (s, 3H). i. METHANESULFONATE 8'[00336] To a stirred solution of alcohol T (69.3 g, 243.7 mmol) and triethylamine(49.2 g, 68.4 mL, 487.0 mmol) in CH2Cl2 (700 mL) at 0 0C was added methanesulfonyl chloride (41.9 g, 28.3 mL, 365.6 mmol). The resulting mixture was stirred at rt. overnight and quenched with water (400 mL). The organic phase was collected, and the aqueous phase was extracted with ethyl acetate. The combined organic phase was washed with 2N HCl (100 mL) and brine (100 mL) and then dried over anhydrous magnesium sulfate. Concentration of the solution under vacuum gave the methanesulfonate 8' as clear oil (86.6 g, 98percent). 1H NMR (400 MHz, CD3Cl3) δ 7.25-7.32 (m. 5H), 4.54 (s, 2H), 4.32-4.34 (m, 2H), 3.71-3.73 (m, 2H), 3.59-3.66 (m, 12H), 3.03 (s, 3H).
89%
Stage #1: With triethylamine In dichloromethane at 0℃; for 0.25 h;
Stage #2: at 0 - 20℃; for 2.50 h;
To a solution of CH2CI2 (20 mL) was added monodispersed tetraethylene glycol monobenzylether 23 (6.21 g, 22 mmol) and cooled to 0° C. in an ice bath. Then triethylamine (3.2 mL, 24 mmol) was added and the reaction mixture was stirred for 15 min at 0° C. Then methanesulfonyl chloride (1.7 mL, 24 mmol) dissolved in CH2CI2 (2 mL) was added and the reaction mixture was stirred at 0° C. for 30 min, the ice bath was removed and the reaction was stirred for an additional 2 h at room temperature. The crude reaction mixture was filtered through Celite (washed CH2CI2, 80 mL) and the filtrate was washed H2O (100 mL), 5percent NaHCO3 (2.x.100 mL), H20 (100 mL), sat. NaCl (100 mL), and dried MgSO4. The resulting yellow oil was chromatographed on a pad of silica containing activated carbon (10 g) to afford the monodispersed compound 24 as a clear oil (7.10 g, 89percent yield).
Reference: [1] Patent: WO2007/112100, 2007, A2. Location in patent: Page/Page column 44; 103; 110; 128-130; 139
[2] Synthesis, 2008, # 2, p. 215 - 220
[3] Journal of Organic Chemistry, 2007, vol. 72, # 25, p. 9679 - 9689
[4] Patent: US2003/229009, 2003, A1. Location in patent: Page 40
[5] Journal of Organic Chemistry, 2006, vol. 71, # 26, p. 9884 - 9886
[6] Chemical Communications, 2014, vol. 50, # 58, p. 7800 - 7802
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Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 4, p. 1371 - 1378
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Reference: [1] Patent: US2003/228275, 2003, A1. Location in patent: Page 44
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Reference: [1] Journal of Organic Chemistry, 2006, vol. 71, # 26, p. 9884 - 9886
[2] Chemical Communications, 2014, vol. 50, # 58, p. 7800 - 7802
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Reference: [1] Chemical Communications, 2014, vol. 50, # 58, p. 7800 - 7802
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