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[ CAS No. 1028432-04-3 ] {[proInfo.proName]}

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Chemical Structure| 1028432-04-3
Chemical Structure| 1028432-04-3
Structure of 1028432-04-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1028432-04-3 ]

CAS No. :1028432-04-3 MDL No. :MFCD11976059
Formula : C13H23NO3SSi Boiling Point : -
Linear Structure Formula :- InChI Key :XWGSCRBSSWZLBD-UHFFFAOYSA-N
M.W : 301.48 Pubchem ID :24899640
Synonyms :

Safety of [ 1028432-04-3 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3259
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1028432-04-3 ]

* 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 [ 1028432-04-3 ]

[ 1028432-04-3 ] Synthesis Path-Downstream   1~82

  • 1
  • [ 1028432-04-3 ]
  • [ 1028432-26-9 ]
  • [ 1028432-17-8 ]
YieldReaction ConditionsOperation in experiment
85% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere;
  • 2
  • [ 619-73-8 ]
  • [ 1028432-04-3 ]
  • [ 1028432-11-2 ]
YieldReaction ConditionsOperation in experiment
97% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.833333h; Inert atmosphere;
97% Stage #1: 4-nitrobenzyl chloride; N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere;
  • 3
  • [ 64196-68-5 ]
  • [ 1028432-04-3 ]
  • C19H31NO5SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere;
  • 4
  • [ 27871-49-4 ]
  • [ 1028432-04-3 ]
  • C17H29NO5SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere;
  • 5
  • [ 10340-23-5 ]
  • [ 1028432-04-3 ]
  • [ 1028432-15-6 ]
YieldReaction ConditionsOperation in experiment
99% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere;
  • 6
  • [ 2749-86-2 ]
  • [ 1028432-04-3 ]
  • [ 1028432-13-4 ]
YieldReaction ConditionsOperation in experiment
100% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere;
100% Stage #1: hex-5-en-2-yn-1-ol; N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere;
  • 7
  • [ 122-97-4 ]
  • [ 1028432-04-3 ]
  • [ 1028432-05-4 ]
YieldReaction ConditionsOperation in experiment
99% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere;
99% Stage #1: 3-Phenyl-1-propanol; N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere;
87% With (phthalocyaninato)iron(II); ethyl 2-(4-cyanophenyl)hydrazinecarboxylate; triphenylphosphine In toluene at 20℃; for 60h; Molecular sieve; Green chemistry;
  • 8
  • [ 1028432-04-3 ]
  • [ 2344-70-9 ]
  • [ 1028432-06-5 ]
YieldReaction ConditionsOperation in experiment
91% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere;
91% Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; 1-phenyl-3-butanol With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere;
  • 9
  • [ 1028432-04-3 ]
  • [ 637-59-2 ]
  • [ 1028432-05-4 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 1.33333h; Inert atmosphere;
With caesium carbonate In N,N-dimethyl-formamide at 60℃;
  • 10
  • [ 1028432-04-3 ]
  • 1-mesitylethanol [ No CAS ]
  • [ 1028432-18-9 ]
YieldReaction ConditionsOperation in experiment
99% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 40℃; Inert atmosphere;
99% Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; 1-mesitylethanol With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 40℃; Inert atmosphere;
  • 11
  • [ 1028432-04-3 ]
  • [ 3742-75-4 ]
  • [ 1028432-05-4 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 1.5h; Inert atmosphere;
With caesium carbonate In N,N-dimethyl-formamide at 60℃;
  • 12
  • [ 1028432-04-3 ]
  • [ 69804-99-5 ]
  • [ 1028432-05-4 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 1.5h; Inert atmosphere;
With caesium carbonate In N,N-dimethyl-formamide at 60℃;
  • 13
  • [ 1028432-04-3 ]
  • [ 132841-84-0 ]
  • [ 1028432-08-7 ]
YieldReaction ConditionsOperation in experiment
97% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere;
97% Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; 7-(phenylseleno)heptan-1-ol With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere;
  • 14
  • [ 1028432-04-3 ]
  • [ 21915-57-1 ]
  • [ 1028432-07-6 ]
YieldReaction ConditionsOperation in experiment
100% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere;
100% Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; 4-(oxiran-2-yl)butyl acetate With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere;
  • 15
  • [ 1028432-04-3 ]
  • [ 105-13-5 ]
  • [ 1028432-10-1 ]
YieldReaction ConditionsOperation in experiment
91% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere;
91% Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; 4-Methoxybenzyl alcohol With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere;
  • 16
  • [ 1028432-04-3 ]
  • [ 4407-36-7 ]
  • [ 1028432-12-3 ]
YieldReaction ConditionsOperation in experiment
99% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere;
  • 17
  • [ 1028432-04-3 ]
  • [ 4064-06-6 ]
  • [ 1028432-09-8 ]
YieldReaction ConditionsOperation in experiment
84% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 1.25h; Inert atmosphere;
84% Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere;
  • 18
  • [ 41879-39-4 ]
  • [ 98-59-9 ]
  • [ 1028432-04-3 ]
YieldReaction ConditionsOperation in experiment
24.6 g In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;
  • 19
  • [ 1028432-04-3 ]
  • [ 1147336-06-8 ]
  • [ 1147336-09-1 ]
YieldReaction ConditionsOperation in experiment
91% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 25℃; Inert atmosphere;
91% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 25℃; for 2h; Inert atmosphere; 16 [0153] To a solution of 4-thienoylfuroxan-3 -methanol (17) (0.5 g, 2.21 mmol) N-(t- butyldimethylsilyloxy)-4-methylbenzenesulfonamide (0.61 g, 2.01 mmol), and triphenylphosphine (1.05 g, 4.02 mmol) in toluene (7.5 mL) and THF (2.5 mL) was added dropwise DEAD (0.84 ml, 2.11 mmol) at 0 0C. The reaction mixture was allowed to attain room temperature in 2 h. The reaction mixture was diluted with ethyl acetate, successively washed with water, saturated NaHCO3, brine and dried (MgSO4). The crude product was purified on a 50 g Biotage silica gel column. Gradient elution with ethyl acetate (2→40%) in hexanes gave the product 18 as white solid: yield 0.93g (1.83 mmol, 91 %). 1H NMR (CDCl3) δ 0.22 (s, 6H, CH3), 0.88 (s, 9H, CH3), 2.49 (s, 3H, CH3), 4.30 (s, 2H, CH2) 7.27 (dd, J= 5.0 Hz and 3.8 Hz, IH, Het-H), 7.39 (d, J= 8.4 Hz, 2H, Ar-H), 7.76 (d, J= 8.4 Hz, 2H, Ar-H), 7.91 (dd, J= 5.0 Hz and 1.0 Hz, IH, Het-H) and 8.31 (dd, J= 4.0 Hz and 1.2 Hz, IH, Het-H); 13C NMR (CDCl3) δ ^l.9, 17.9, 21.7, 25.8, 47.8, 110.7, 128.2, 129.1, 129.5, 130.5, 137.5, 137.6, 140.4, 145.6, 153.6 and 175.1.
  • 20
  • [ 1028432-04-3 ]
  • [ 362-75-4 ]
  • [ 1142935-23-6 ]
YieldReaction ConditionsOperation in experiment
81% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃;
  • 21
  • [ 19748-66-4 ]
  • [ 1028432-04-3 ]
  • [ 1259031-90-7 ]
  • 22
  • [ 4441-30-9 ]
  • [ 1028432-04-3 ]
  • [ 1259031-91-8 ]
YieldReaction ConditionsOperation in experiment
98% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere;
  • 23
  • [ 5317-33-9 ]
  • [ 1028432-04-3 ]
  • [ 1259031-92-9 ]
  • 24
  • [ 1028432-04-3 ]
  • [ 1259031-78-1 ]
  • [ 1259031-83-8 ]
YieldReaction ConditionsOperation in experiment
97% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere;
  • 25
  • [ 1028432-04-3 ]
  • [ 1259031-79-2 ]
  • [ 1259031-85-0 ]
YieldReaction ConditionsOperation in experiment
96% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere;
  • 26
  • [ 1028432-04-3 ]
  • [ 1259031-80-5 ]
  • [ 1259031-86-1 ]
YieldReaction ConditionsOperation in experiment
97% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere;
  • 27
  • [ 1028432-04-3 ]
  • [ 1259031-81-6 ]
  • [ 1259031-87-2 ]
YieldReaction ConditionsOperation in experiment
96% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere;
  • 28
  • [ 1028432-04-3 ]
  • [ 1259031-77-0 ]
  • [ 1259031-82-7 ]
YieldReaction ConditionsOperation in experiment
98% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere;
  • 29
  • [ 104-58-5 ]
  • [ 1028432-04-3 ]
  • [ 1259031-89-4 ]
YieldReaction ConditionsOperation in experiment
96% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere;
  • 30
  • [ 86368-07-2 ]
  • [ 1028432-04-3 ]
  • [ 1259031-88-3 ]
YieldReaction ConditionsOperation in experiment
99% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere;
  • 31
  • [ 1028432-04-3 ]
  • [ 17719-78-7 ]
  • [ 1259031-84-9 ]
YieldReaction ConditionsOperation in experiment
96% With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere;
  • 32
  • [ 1028432-04-3 ]
  • [ 1270026-72-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 0 °C 2: trifluorormethanesulfonic acid / dichloromethane; water; acetonitrile / 1 h / 0 °C
  • 33
  • [ 1028432-04-3 ]
  • [ 73696-28-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 0 °C 2: trifluorormethanesulfonic acid / dichloromethane; water; acetonitrile / 1 h / 0 °C 3: [Au(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(NTf2)] / toluene / 1 h / 60 °C / Molecular sieve
  • 34
  • [ 1028432-04-3 ]
  • [ 927-74-2 ]
  • C17H27NO3SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃;
  • 35
  • [ 4356-69-8 ]
  • [ 1028432-04-3 ]
  • 1,1-bis(4-methoxyphenyl)-2-tosylethene [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With manganese(IV) oxide; 2-(2-(4,5-dihydrooxazol-2-yl)propan-2-yl)-4,5-dihydrooxazole; copper(II) bis(trifluoromethanesulfonate) In toluene at 120℃; for 24h; Inert atmosphere; Molecular sieve;
  • 36
  • [ 1028432-04-3 ]
  • [ 104-54-1 ]
  • C22H31NO3SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; 3-Phenylpropenol With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere;
  • 37
  • [ 547-64-8 ]
  • [ 1028432-04-3 ]
  • [ 1028432-16-7 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: methyl lactate; N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere;
  • 38
  • [ 1028432-04-3 ]
  • C16H24O3 [ No CAS ]
  • C29H45NO5SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; C16H24O3 With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere;
  • 39
  • [ 1028432-04-3 ]
  • [ 81028-03-7 ]
  • [ 1613337-88-4 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; (Z)-4-benzyloxy-but-2-en-1-ol With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere;
  • 40
  • 3-nonene-1-ol [ No CAS ]
  • [ 1028432-04-3 ]
  • C22H39NO2SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: 3-nonene-1-ol; N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere;
  • 41
  • [ 1028432-04-3 ]
  • [ 27977-16-8 ]
  • C19H31NO5SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; acetic acid 4-hydroxybut-2-enyl ester With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere;
  • 42
  • [ 18162-48-6 ]
  • [ 98-59-9 ]
  • [ 1028432-04-3 ]
YieldReaction ConditionsOperation in experiment
69% Stage #1: tert-butyldimethylsilyl chloride With hydroxylamine hydrochloride In N,N-dimethyl-formamide for 0.5h; Cooling with ice; Stage #2: With triethylamine In N,N-dimethyl-formamide at 10℃; Stage #3: p-toluenesulfonyl chloride In N,N-dimethyl-formamide at 10℃;
  • 43
  • [ 1028432-04-3 ]
  • 3-[6-chloro-2-(2-thienyl)quinolin-3-yl]-1-propanol [ No CAS ]
  • N-(tert-butyldimethylsilyloxy)-N-[3-(6-chloro-2-(2-thienyl)quinolin-3-yl)propyl]-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; for 0.0833333h; 23 N-(tert-butyldimethylsilyloxy)-N-[3-(6-chloro-2-(2-thienyl)quinolin-3-yl)propyl]-4-methylbenzenesulfonamide 46 To a solution of alcohol 45 (400 mg, 1.32 mmol) in anhydrous toluene (4 mL) and THF (1.2 mL), N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide (397 mg, 1.32 mmol) and PPh3 (691 mg, 2.63 mmol) were added. The mixture was cooled to 0 °C and treated dropwise with DEAD (40% solution in toluene, 0.86 mL, 1.98 mmol). The reaction mixture was stirred at room temperature for 5 min, concentrated at reduced pressure and purified through column chromatography (35-70 μm silica gel, hexane/EtOAc mixtures, gradient elution). On elution with hexane/EtOAc 90:10, slightly impure 46 (913 mg) was isolated; Rf 0.60 (hexane/EtOAc 1:1); mp 91-92 °C; IR (ATR) N-(tert-butyldimethylsilyloxy)-N-[3-(6-chloro-2-(2-thienyl)quinolin-3-yl)propyl]-4-methylbenzenesulfonamide 46 ν 1594, 1548, 1522 (Ar-C-C and Ar-C-N st), 1359, 1168 (SO2) cm-1; 1H NMR (400 MHz, CDCl3) δ 0.09 [s, 6H, Si(CH3)2], 0.72 [s, 9H, Si[C(CH3)3]], 1.80 (tt, J = J' = 7.4 Hz, 2H, 2-H2), 2.25 (s, 3H, tosyl CH3), 2.81 (t, J = 7.2 Hz, 2H), 2.90 (t, J = 7.6 Hz, 2H) (1-H2 and 3-H2), 6.97 (dd, J = 4.8 Hz, J' = 4.0 Hz, 1H, 4"-H), 7.09-7.18 (complex signal), 7.20-7.24 (complex signal) [4H, 3"-H, 5"-H, and tosyl-C3(5)-H], 7.42 (dd, J = 9.2 Hz, J' = 2.0 Hz, 1H, 7'-H), 7.51 [br d, J = 8.4 Hz, 2H, tosyl-C2(6)-H], 7.57 (d, J = 2.0 Hz, 1H, 5'-H), 7.74 (s, 1H, 4'-H), 7.85 (d, J = 9.2 Hz, 1H, 8'-H); 13C NMR (100.6 MHz, CDCl3) δ - 4.1 [2CH3, Si(CH3)3], 18.4 [C, SiC(CH3)3], 21.8 (CH3, tosyl CH3), 26.1 [3CH3, SiC(CH3)3], 27.3 (CH2, C2), 30.8 (CH2, C3), 55.4 (CH2, C1), significant aromatic signals: 125.7 (CH, C8'), 129.5 [2CH, tosyl-C3(5)], 130.0 [2CH, tosyl-C2(6)], 132.4 (C), 132.8 (C) (C6', C8a'), 136.0 (CH, C4'), 144.8 (C, C3'), 152.9 (C, C2'); HRMS (ESI), calcd for [C29H3535ClN2O3S2Si + H+] 587.1620, found 587.1596.
  • 44
  • [ 1028432-04-3 ]
  • [ 94966-45-7 ]
  • N-(1-(4-bromophenyl)-3,3-diphenylpropa-1,2-dien-1-yl)-N-((tertbutyldimethylsilyl)oxy)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve;
  • 45
  • [ 1028432-04-3 ]
  • 1,1-diphenyl-10-(triisopropylsilyl)deca-2,9-diyn-1-ol [ No CAS ]
  • N-((tert-butyldimethylsilyl)oxy)-N-(1,1-diphenyl-10-(triisopropylsilyl)-deca-1,2-dien-9-yn-3-yl)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
24% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve;
  • 46
  • [ 1028432-04-3 ]
  • 1-phenyl-1-(o-tolyl)hept-2-yn-1-ol [ No CAS ]
  • N-((tert-butyldimethylsilyl)oxy)-4-methyl-N-(1-phenyl-1-(o-tolyl)-hepta-1,2-dien-3-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
17% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve;
  • 47
  • [ 1028432-04-3 ]
  • [ 18215-68-4 ]
  • N-((tert-butyldimethylsilyl)oxy)-N-(1,1-diphenylhepta-1,2-dien-3-yl)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve;
  • 48
  • [ 1028432-04-3 ]
  • (E)-1,1-diphenyl-2-tosylhept-1-en-3-one oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C
  • 49
  • [ 1028432-04-3 ]
  • (E)-1,1-diphenyl-2-tosylhept-1-en-3-one O-(4-bromobenzoyl)oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C 3: triethylamine; dmap / dichloromethane / 15 h / 20 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C 3: triethylamine; dmap / dichloromethane / 15 h / 20 °C / Inert atmosphere
  • 50
  • [ 1028432-04-3 ]
  • 3,3-diphenyl-2-tosylacrylaldehyde oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C
  • 51
  • [ 1028432-04-3 ]
  • 1-cyclohexyl-3,3-diphenyl-2-tosylprop-2-en-1-one oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C
  • 52
  • [ 1028432-04-3 ]
  • 1-phenoxy-4,4-diphenyl-3-tosylbut-3-en-2-one oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C
  • 53
  • [ 1028432-04-3 ]
  • 1,1-bis(4-chlorophenyl)-2-tosylhept-1-en-3-one oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C
  • 54
  • [ 1028432-04-3 ]
  • [ 1415035-10-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: silver fluoride / acetonitrile / 20 °C
  • 55
  • [ 1522-13-0 ]
  • [ 1028432-04-3 ]
  • N-((tert-butyldimethylsilyl)oxy)-4-methyl-N-(1,3,3-triphenylpropa-1,2-dien-1-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve;
  • 56
  • [ 1522-13-0 ]
  • [ 1028432-04-3 ]
  • 1,3,3-triphenyl-2-tosylprop-2-en-1-one oxime [ No CAS ]
  • 3,5,5-triphenyl-4-tosyl-4,5-dihydroisoxazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C
  • 57
  • [ 1028432-04-3 ]
  • [ 3923-52-2 ]
  • N-((tert-butyldimethylsilyl)oxy)-N-(3,3-diphenylpropa-1,2-dien-1-yl)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
12% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve;
  • 58
  • [ 1028432-04-3 ]
  • 3-cyclohexyl-1,1-diphenylprop-2-yn-1-ol [ No CAS ]
  • N-((tert-butyldimethylsilyl)oxy)-N-(1-cyclohexyl-3,3-diphenylpropa-1,2-dien-1-yl)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
14% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve;
  • 59
  • [ 1028432-04-3 ]
  • [ 16464-46-3 ]
  • N-((tert-butyldimethylsilyl)oxy)-4-methyl-N-(1-phenoxy-4,4-diphenylbuta-2,3-dien-2-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
6% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve;
  • 60
  • [ 1028432-04-3 ]
  • 1,1'-bis(4-chlorophenyl)hept-2-yn-1-ol [ No CAS ]
  • N-(1,1-bis(4-chlorophenyl)hepta-1,2-dien-3-yl)-N-((tert-butyldimethylsilyl)oxy)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve;
  • 61
  • [ 1028432-04-3 ]
  • 1,1'-bis(4-methoxyphenyl)hept-2-yn-1-ol [ No CAS ]
  • N-(1,1-bis(4-methoxyphenyl)hepta-1,2-dien-3-yl)-N-((tert-butyldimethylsilyl)oxy)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve;
  • 62
  • [ 1028432-04-3 ]
  • [ 344259-19-4 ]
  • N-(2-(cyclohex-2-en-1-yl)ethyl)-N-((tert-butyldimethylsilyl)oxy)-4-toluenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With caesium carbonate In N,N-dimethyl-formamide for 17h;
  • 64
  • [ 1028432-04-3 ]
  • C15H19NO2S [ No CAS ]
  • (3aR*,7aS*)-1-tosyl-2,3,3a,4,5,7a-hexahydro-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 17 h 2: pyridine hydrogenfluoride / tetrahydrofuran / 20 °C 3: 1 h 4: tris-(dibenzylideneacetone)dipalladium(0); tris<3,5-bis(trifluoromethyl)phenyl>phosphane; triethylamine / N,N-dimethyl-formamide / 80 °C / Inert atmosphere; Sealed tube
Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 17 h 2: pyridine hydrogenfluoride / tetrahydrofuran / 20 °C 3: triethylamine / dichloromethane / 0 - 20 °C 4: tris-(dibenzylideneacetone)dipalladium(0); tris<3,5-bis(trifluoromethyl)phenyl>phosphane; triethylamine / N,N-dimethyl-formamide / 80 °C / Inert atmosphere; Sealed tube
  • 65
  • [ 1028432-04-3 ]
  • N-(2-(cyclohex-2-en-1-yl)ethyl)-N-hydroxy-4-toluenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 17 h 2: pyridine hydrogenfluoride / tetrahydrofuran / 20 °C
  • 66
  • [ 1028432-04-3 ]
  • N-2-(cyclohex-2-en-1-yl)ethyl-N-(methanesulfonyloxy)-4-toluenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 17 h 2: pyridine hydrogenfluoride / tetrahydrofuran / 20 °C 3: triethylamine / dichloromethane / 0 - 20 °C
  • 67
  • [ 1028432-04-3 ]
  • N-2-(cyclohex-2-en-1-yl)ethyl-N-(trifluoroacetyloxy)-4-toluenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 17 h 2: pyridine hydrogenfluoride / tetrahydrofuran / 20 °C 3: 1 h
  • 68
  • [ 1028432-04-3 ]
  • C35H54N2O10SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: caesium carbonate / acetonitrile / 2 h / 20 °C / Inert atmosphere 2.1: ethylmagnesium bromide / tetrahydrofuran; diethyl ether / 0.33 h / 0 - 20 °C / Inert atmosphere 2.2: 0.5 h / 0 °C / Inert atmosphere
  • 69
  • [ 1028432-04-3 ]
  • C35H56N2O10SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: caesium carbonate / acetonitrile / 2 h / 20 °C / Inert atmosphere 2.1: ethylmagnesium bromide / tetrahydrofuran; diethyl ether / 0.33 h / 0 - 20 °C / Inert atmosphere 2.2: 0.5 h / 0 °C / Inert atmosphere 3.1: palladium 10% on activated carbon; quinoline; hydrogen / ethanol; ethyl acetate / 1.5 h / 20 °C
  • 70
  • [ 1028432-04-3 ]
  • [ 106-96-7 ]
  • C16H25NO3SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
96.5% With caesium carbonate In acetonitrile at 20℃; for 2h; Inert atmosphere;
  • 71
  • [ 1028432-04-3 ]
  • 6-hydroxy-6,6-diphenylhex-4-yn-1-yl acetate [ No CAS ]
  • 4-( (N-((tert-butyldimethylsi l y l )oxy)-4-methylphenyl)sulfonamido)-6,6-diphenylhexa-4,5-dien-1-yl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 0.5h; Molecular sieve; Inert atmosphere;
  • 72
  • [ 1028432-04-3 ]
  • 7-hydroxy-7,7-diphenylhept-5-yn-1-yl acetate [ No CAS ]
  • 5-( (N-((tert-butyldimethylsilyl)oxy)-4-methylphenyl)sulfonamido)-7,7-diphenylhepta-5,6-dien-1-yl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 0.5h; Molecular sieve; Inert atmosphere;
  • 73
  • [ 1028432-04-3 ]
  • 5-hydroxy-5,5-diphenylpent-3-yn-1-yl acetate [ No CAS ]
  • 3-((N-((tert-butyldimethylsi lyl)oxy)-4-methylphenyl)sulfonamido)-5,5-diphenylpenta-3,4-dien-1-yl acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 0.5h; Molecular sieve; Inert atmosphere;
  • 74
  • [ 1028432-04-3 ]
  • N-(4-hydroxy-4,4-diphenylbut-2-yn-1-yl)-4-methylbenzenesulfonamide [ No CAS ]
  • N-((tert-butyldimethylsilyl)oxy)-4-methyl-N-(1-((4-methylphenyl)-sulfonamido)-4,4-diphenylbuta-2,3-dien-2-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -90 - 20℃; Molecular sieve; Inert atmosphere;
  • 75
  • [ 1028432-04-3 ]
  • diethyl 2-(5-hydroxy-5,5-diphenylpent-3-yn-1-yl)malonate [ No CAS ]
  • diethyl 2-(3-((N-((tert-butyldimethylsilyl)oxy)-4-methylphenyl)sulfonamido)-5,5-diphenylpenta-3,4-dien-1-yl)malonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -90 - 20℃; Molecular sieve; Inert atmosphere;
  • 76
  • [ 1028432-04-3 ]
  • diethyl 2-(4-hydroxy-4,4-diphenylbut-2-yn-1-yl)malonate [ No CAS ]
  • diethyl 2-(2-((N-((tert-butyldimethylsilyl)oxy)-4-methylphenyl)sulfonamido)-4,4-diphenylbuta-2,3-dien-1-yl)malonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -90 - 20℃; Molecular sieve; Inert atmosphere;
  • 77
  • [ 1028432-04-3 ]
  • N-((tert-butyldimethylsilyl)oxy)-N-(5-hydroxy-1,1-diphenylpenta-1,2-dien-3-yl)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / -78 °C / Molecular sieve; Inert atmosphere 2: sodium methylate / methanol / 5 h / 20 °C
  • 78
  • [ 1028432-04-3 ]
  • S-(3-((N-((tert-butyldimethylsilyl)oxy)-4-methylphenyl)sulfonamido)-5,5-diphenylpenta-3,4-dien-1-yl) ethanethioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / -78 °C / Molecular sieve; Inert atmosphere 2: sodium methylate / methanol / 5 h / 20 °C 3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.17 h / 0 - 20 °C / Inert atmosphere
  • 79
  • [ 1028432-04-3 ]
  • N-((tert-butyldimethylsilyl)oxy)-N-(5-(1,3-dioxoisoindolin-2-yl)-1,1-diphenylpenta-1,2-dien-3-yl)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / -78 °C / Molecular sieve; Inert atmosphere 2: sodium methylate / methanol / 5 h / 20 °C 3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere
  • 80
  • [ 1028432-04-3 ]
  • N-((tert-butyldimethylsilyl)oxy)-4-methyl-N-(5-((4-methylphenyl)-sulfonamido)-1,1-diphenylpenta-1,2-dien-3-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / -78 °C / Molecular sieve; Inert atmosphere 2.1: sodium methylate / methanol / 5 h / 20 °C 3.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere 4.1: hydrazine hydrate / chloroform; methanol / 3 h / 0 - 20 °C 4.2: 0 - 20 °C
  • 81
  • [ 1028432-04-3 ]
  • 3-(inden-2-yl)but-2-en-1-ol [ No CAS ]
  • C26H35NO3SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.166667h; Inert atmosphere; 3-(Inden-2-yl)but-2-enal oxime (13) DEAD (40% in toluene, 0.15 mL, 0.32 mmol) was added slowly to a mixture of 2-alkenylindole 11 (150 mg, 0.81 mmol), O-TBS-N-tosylhydroxylamine (218 mg, 0.72mmol), and PPh3 (424 mg, 1.62 mmol) in toluene (6 mL) and THF (2 mL) at 0 °C. After stirring at the temperature for 10 min, the solvent was evaporated to half an amount. The mixture was dissolved in MeCN (10 mL), and CsF (245 mg, 1.62 mmol) was added. After stirring at rt for 1 h, saturated NH4Cl aq.was added and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by column chromatography using EtOAc-hexane (3:7, v/v)as an eluent to give the oxime 13 (123 mg, 76%) as yellow solid. 1H-NMR (CDCl3) δ: 8.23 (2/3H, d, J = 10.4 Hz), 7.61 (1/3H, d, J = 10.4 Hz), 7.46 (1/3H, d, J = 7.2 Hz), 7.42 (2/3H, d, J = 7.2 Hz), 7.41 (1H/3, d,J = 7.2 Hz), 7.36 (2/3H, d, J = 7.2 Hz), 7.30 (1/3H, t, J = 7.2 Hz), 7.27 (1/3H, t, J = 7.2 Hz), 7.23 (2/3H, d,J = 7.2 Hz), 7.19 (2/3H, d, J = 7.2 Hz), 7.00 (2/3H, s), 6.98 (1/3H, s), 6.72 (1/3H, d, J = 10.4 Hz), 6.43(2/3H, d, J = 10.4 Hz), 3.64 (4/3H, s), 3.63 (2/3H, s), 2.20 (3/3H, s), 2.18 (6/3H, s), one proton (OH) wasnot observed. MS m/z: 199 (M+). HRMS (EI) calcd for C13H13NO 199.0997; found 199.0988.
  • 82
  • [ 1028432-04-3 ]
  • C8H6ClN3O2 [ No CAS ]
  • C21H28N4O5SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; C8H6ClN3O2 With potassium carbonate; sodium iodide In acetonitrile at 20℃; Stage #2: With dmap In dichloromethane at 20℃;
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