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[ CAS No. 125486-96-6 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 125486-96-6
Chemical Structure| 125486-96-6
Structure of 125486-96-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 125486-96-6 ]

CAS No. :125486-96-6 MDL No. :MFCD09265152
Formula : C5H15NO2SSi Boiling Point : -
Linear Structure Formula :- InChI Key :MZASHBBAFBWNFL-UHFFFAOYSA-N
M.W : 181.33 Pubchem ID :11008553
Synonyms :

Calculated chemistry of [ 125486-96-6 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.69
TPSA : 68.54 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.89
Log Po/w (XLOGP3) : 1.12
Log Po/w (WLOGP) : 1.69
Log Po/w (MLOGP) : -0.09
Log Po/w (SILICOS-IT) : -1.51
Consensus Log Po/w : 0.42

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.47
Solubility : 6.12 mg/ml ; 0.0337 mol/l
Class : Very soluble
Log S (Ali) : -2.15
Solubility : 1.28 mg/ml ; 0.00703 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.52
Solubility : 5.46 mg/ml ; 0.0301 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.13

Safety of [ 125486-96-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 125486-96-6 ]

* 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 [ 125486-96-6 ]

[ 125486-96-6 ] Synthesis Path-Downstream   1~87

  • 3
  • [ 55628-54-1 ]
  • [ 125486-96-6 ]
  • [ 183989-07-3 ]
YieldReaction ConditionsOperation in experiment
78% With iodonium(di-γ-collidine) perchlorate; 4 A molecular sieve In dichloromethane at 0℃;
  • 4
  • [ 14371-10-9 ]
  • [ 125486-96-6 ]
  • N-(trans-3-phenylprop-2-enylidene)-β-trimethylsilylethanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With boron trifluoride diethyl etherate In toluene Heating;
69% With boron trifluoride diethyl etherate In benzene Heating;
  • 5
  • [ 125486-96-6 ]
  • [ 100-52-7 ]
  • N-benzylidene-β-trimethylsilylethanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With boron trifluoride diethyl etherate In benzene for 24h; Heating;
72% With boron trifluoride diethyl etherate In toluene Heating;
  • 6
  • [ 3240-34-4 ]
  • [ 125486-96-6 ]
  • [ 236122-13-7 ]
YieldReaction ConditionsOperation in experiment
99% With potassium hydroxide In methanol 1.) 0 deg C, 30 min, 2.) 20 deg C, 3 h;
  • 7
  • [ 125486-96-6 ]
  • [ 30383-01-8 ]
  • [ 895140-72-4 ]
  • [ 351209-70-6 ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 2-(trimethylsilyl)ethanesulfonamide; (2R,3S,4R)-4-Benzyloxy-2-benzyloxymethyl-3-[(2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-3,4-dihydro-2H-pyran With iodonium(di-γ-collidine) perchlorate Stage #2: lithium thioethoxide In N,N-dimethyl-formamide at -40 - 0℃;
  • 8
  • [ 100-42-5 ]
  • [ 125486-96-6 ]
  • [ 236122-14-8 ]
YieldReaction ConditionsOperation in experiment
97% With tert-butylhypochlorite; sodium iodide In acetonitrile at 20℃; for 3h;
68% With iodosylbenzene; 3 A molecular sieve In acetonitrile at 20℃; for 20h;
  • 9
  • [ 498-66-8 ]
  • [ 125486-96-6 ]
  • 3-(2-trimethylsilanyl-ethanesulfonyl)-3-aza-tricyclo[3.2.1.02,4]octane [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With iodosylbenzene; 3 A molecular sieve In acetonitrile at 20℃; for 20h;
  • 10
  • [ 6622-76-0 ]
  • [ 125486-96-6 ]
  • [ 359715-85-8 ]
YieldReaction ConditionsOperation in experiment
48% With iodosylbenzene; 3 A molecular sieve In acetonitrile at 20℃; for 20h;
  • 11
  • [ 125486-96-6 ]
  • [ 103-26-4 ]
  • [ 359715-80-3 ]
YieldReaction ConditionsOperation in experiment
53% With iodosylbenzene; 3 A molecular sieve In acetonitrile at 20℃; for 20h;
  • 12
  • [ 125486-96-6 ]
  • [ 80-62-6 ]
  • N-(2-(trimethylsilyl)ethanesulfonyl)-2-(methoxycarbonyl)-2-methylaziridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With iodosylbenzene; 3 A molecular sieve In acetonitrile at 20℃; for 20h;
  • 13
  • [ 125486-96-6 ]
  • [ 110-83-8 ]
  • N-(2-(trimethylsilyl)ethanesulfonyl)-7-azabicyclo<4.1.0>heptane [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With iodosylbenzene; 3 A molecular sieve In acetonitrile at 20℃; for 20h;
  • 14
  • [ 498-60-2 ]
  • [ 125486-96-6 ]
  • N-1[(E)-(3-furyl)methylidene]-2-(trimethylsilyl)-1-ethanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With boron trifluoride diethyl etherate In toluene for 3h; Heating;
  • 15
  • [ 5414-21-1 ]
  • [ 125486-96-6 ]
  • [ 652130-73-9 ]
YieldReaction ConditionsOperation in experiment
76% With caesium carbonate In N,N-dimethyl-formamide at 20℃;
  • 16
  • [ 6621-59-6 ]
  • [ 125486-96-6 ]
  • [ 652130-74-0 ]
YieldReaction ConditionsOperation in experiment
73% With caesium carbonate In N,N-dimethyl-formamide at 20℃;
  • 18
  • [ 500-22-1 ]
  • [ 125486-96-6 ]
  • [ 292638-85-8 ]
  • methyl 2-(pyridin-3-yl(2-(trimethylsilyl)ethylsulfonamido)methyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With titanium(IV) isopropylate; molecular sieve; 3-quinuclidinol In isopropyl alcohol at 70℃; for 6h;
  • 19
  • [ 98-01-1 ]
  • [ 125486-96-6 ]
  • [ 292638-85-8 ]
  • methyl 2-(furan-2-yl(2-(trimethylsilyl)ethylsulfonamido)methyl)acrylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 70℃; for 6h;
  • 20
  • [ 7797-83-3 ]
  • [ 125486-96-6 ]
  • [ 292638-85-8 ]
  • [ 816457-70-2 ]
YieldReaction ConditionsOperation in experiment
66% With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 70℃; for 72h;
  • 21
  • [ 125486-96-6 ]
  • [ 104-88-1 ]
  • [ 292638-85-8 ]
  • [ 816457-71-3 ]
YieldReaction ConditionsOperation in experiment
86% With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 70℃; for 14h;
  • 22
  • [ 125486-96-6 ]
  • [ 555-16-8 ]
  • [ 292638-85-8 ]
  • [ 816457-74-6 ]
YieldReaction ConditionsOperation in experiment
60% With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 70℃; for 6h;
  • 23
  • [ 18143-40-3 ]
  • [ 125486-96-6 ]
YieldReaction ConditionsOperation in experiment
67% Stage #1: sodium β-trimethylsilylethanesulfonate With phosphorus pentachloride In dichloromethane at 20℃; for 0.5h; Stage #2: With ammonia In dichloromethane at -10℃; for 0.25h;
  • 25
  • [ 125486-96-6 ]
  • [ 66-99-9 ]
  • [ 292638-85-8 ]
  • [ 816457-67-7 ]
YieldReaction ConditionsOperation in experiment
60% With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 70℃; for 48h;
  • 26
  • [ 26260-02-6 ]
  • [ 125486-96-6 ]
  • [ 292638-85-8 ]
  • [ 816457-72-4 ]
YieldReaction ConditionsOperation in experiment
73% With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 70℃; for 10h;
  • 27
  • [ 5779-95-3 ]
  • [ 125486-96-6 ]
  • [ 292638-85-8 ]
  • [ 816457-69-9 ]
YieldReaction ConditionsOperation in experiment
70% With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 70℃; for 72h;
  • 29
  • [ 125486-96-6 ]
  • [ 77123-57-0 ]
  • [ 292638-85-8 ]
  • [ 816457-73-5 ]
YieldReaction ConditionsOperation in experiment
61% With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 70℃; for 14h;
  • 30
  • [ 125486-96-6 ]
  • [ 292638-85-8 ]
  • [ 6630-33-7 ]
  • [ 816457-66-6 ]
YieldReaction ConditionsOperation in experiment
86% With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 70℃; for 6h;
  • 31
  • [ 125486-96-6 ]
  • [ 292638-85-8 ]
  • [ 620-23-5 ]
  • [ 816457-68-8 ]
YieldReaction ConditionsOperation in experiment
86% With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 70℃; for 38h;
  • 32
  • [ 125486-96-6 ]
  • [ 292638-85-8 ]
  • [ 1571-08-0 ]
  • [ 816457-63-3 ]
YieldReaction ConditionsOperation in experiment
90% With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 70℃; for 6h;
  • 33
  • [ 125486-96-6 ]
  • [ 292638-85-8 ]
  • [ 456-48-4 ]
  • [ 816457-65-5 ]
YieldReaction ConditionsOperation in experiment
79% With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 70℃; for 6h;
  • 34
  • [ 24424-99-5 ]
  • [ 125486-96-6 ]
  • [ 145387-82-2 ]
YieldReaction ConditionsOperation in experiment
90% With dmap; triethylamine In dichloromethane at 20℃;
  • 35
  • [ 1193-82-4 ]
  • [ 125486-96-6 ]
  • [ 452898-05-4 ]
YieldReaction ConditionsOperation in experiment
83% With [bis(acetoxy)iodo]benzene; silver nitrate; 4,4',4-tri-tert-butyl-2,2':6',2-terpyridine In acetonitrile at 20℃; for 168h;
70% With iron(II) triflate; iodosylbenzene In acetonitrile at 20℃; Molecular sieve;
66% With iodosylbenzene In acetonitrile at 20℃; for 18h;
  • 36
  • [ 125486-96-6 ]
  • [ 132911-87-6 ]
  • 2-Trimethylsilanyl-ethanesulfonic acid [(2S,3S,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-iodo-tetrahydro-pyran-3-yl]-amide [ No CAS ]
  • 2-Trimethylsilanyl-ethanesulfonic acid [(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-iodo-tetrahydro-pyran-3-yl]-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 75% 2: 12% Stage #1: 2-(trimethylsilyl)ethanesulfonamide; 4-=-(3-O-allyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-3,6-di-O-benzyl-D-arabino-hex-1-enitol In dichloromethane at 20℃; for 0.5h; Stage #2: With Ag(collidine)2ClO4; iodine In dichloromethane at 0℃; for 1.5h;
  • 37
  • [ 125486-96-6 ]
  • [ 292638-85-8 ]
  • [ 105-07-7 ]
  • [ 929012-64-6 ]
YieldReaction ConditionsOperation in experiment
80% With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 70℃; for 6h;
  • 38
  • [ 125486-96-6 ]
  • [ 105-45-3 ]
  • C10H21NO4SSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With toluene-4-sulfonic acid In benzene Heating;
  • 39
  • C12H20O3 [ No CAS ]
  • [ 125486-96-6 ]
  • C17H33NO4SSiH2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;
  • 40
  • [ 125486-96-6 ]
  • [ 212071-06-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / dimethylformamide 2: 2nd generation Grubbs catalyst / CH2Cl2
Multi-step reaction with 3 steps 1: 86 percent / 1,4-diazabicyclo[2.2.2]octane / propan-2-ol / 10 h / 70 °C 2: 98 percent / K2CO3 / dimethylformamide / 6 h / 20 °C 3: 98 percent / Cl2(PCyhex3)(N1,N3-dimesyl-imidazol-2-yl)benzylidene Ru(VI) / CH2Cl2 / 5 h / 100 °C / microwave irradiation
Multi-step reaction with 2 steps 1: 82 percent / BF3*OEt2 / benzene / 24 h / Heating 2: 96 percent / PPh3 / benzene / Ambient temperature
  • 41
  • [ 125486-96-6 ]
  • [ 223581-87-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: CHCl3 / Heating 2: (R)-Tol-BINAP*CuClO4*2MeCN / tetrahydrofuran / 24 h / 0 - 20 °C
Multi-step reaction with 2 steps 1: 93 percent / CHCl3 / Heating 2: 78 percent / (R)Tol-BINAP; CuClO4*(CH3CN)2 / CH2Cl2
  • 42
  • 1-(p-methoxyphenyl)ethyl acetate [ No CAS ]
  • [ 125486-96-6 ]
  • [ 1025359-75-4 ]
YieldReaction ConditionsOperation in experiment
78% With t-BuOOAc In 1,2-dichloro-ethane at 25℃; for 6h;
  • 43
  • [ 129825-11-2 ]
  • [ 125486-96-6 ]
  • [ 1045771-63-8 ]
YieldReaction ConditionsOperation in experiment
84% With caesium carbonate In 1,4-dioxane at 120℃; for 15h;
  • 44
  • [ 109-09-1 ]
  • [ 125486-96-6 ]
  • [ 1045771-58-1 ]
YieldReaction ConditionsOperation in experiment
67% With caesium carbonate In 1,4-dioxane at 120℃; for 15h;
  • 45
  • [ 109-04-6 ]
  • [ 125486-96-6 ]
  • [ 1045771-58-1 ]
YieldReaction ConditionsOperation in experiment
85% With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
  • 46
  • [ 1722-12-9 ]
  • [ 125486-96-6 ]
  • [ 1045771-69-4 ]
YieldReaction ConditionsOperation in experiment
90% With caesium carbonate In 1,4-dioxane at 120℃; for 15h;
  • 47
  • [ 18368-76-8 ]
  • [ 125486-96-6 ]
  • [ 1045771-67-2 ]
  • 48
  • [ 33252-30-1 ]
  • [ 125486-96-6 ]
  • [ 1045771-68-3 ]
YieldReaction ConditionsOperation in experiment
80% With caesium carbonate In 1,4-dioxane at 120℃; for 15h;
  • 49
  • [ 39856-50-3 ]
  • [ 125486-96-6 ]
  • [ 1045771-57-0 ]
YieldReaction ConditionsOperation in experiment
85% With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
  • 50
  • [ 108-86-1 ]
  • [ 125486-96-6 ]
  • [ 1045771-47-8 ]
YieldReaction ConditionsOperation in experiment
85% With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
  • 51
  • [ 83-42-1 ]
  • [ 125486-96-6 ]
  • [ 1045771-66-1 ]
  • 52
  • [ 1126-46-1 ]
  • [ 125486-96-6 ]
  • [ 1045771-60-5 ]
YieldReaction ConditionsOperation in experiment
90% With caesium carbonate In 1,4-dioxane at 120℃; for 15h;
  • 53
  • [ 939-80-0 ]
  • [ 125486-96-6 ]
  • [ 1045771-61-6 ]
  • 54
  • [ 5465-65-6 ]
  • [ 125486-96-6 ]
  • [ 1045771-62-7 ]
YieldReaction ConditionsOperation in experiment
89% With caesium carbonate In 1,4-dioxane at 120℃; for 15h;
  • 55
  • [ 16588-02-6 ]
  • [ 125486-96-6 ]
  • [ 1045771-64-9 ]
  • 56
  • [ 6952-59-6 ]
  • [ 125486-96-6 ]
  • [ 1045771-50-3 ]
YieldReaction ConditionsOperation in experiment
88% With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
  • 57
  • [ 24398-88-7 ]
  • [ 125486-96-6 ]
  • [ 1045771-48-9 ]
YieldReaction ConditionsOperation in experiment
95% With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
  • 58
  • [ 5798-75-4 ]
  • [ 125486-96-6 ]
  • [ 1045771-43-4 ]
YieldReaction ConditionsOperation in experiment
98% With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
  • 59
  • [ 90-11-9 ]
  • [ 125486-96-6 ]
  • [ 1045771-56-9 ]
YieldReaction ConditionsOperation in experiment
82% With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
  • 60
  • [ 623-00-7 ]
  • [ 125486-96-6 ]
  • [ 1045771-46-7 ]
YieldReaction ConditionsOperation in experiment
91% With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
  • 61
  • [ 577-19-5 ]
  • [ 125486-96-6 ]
  • [ 1045771-53-6 ]
YieldReaction ConditionsOperation in experiment
85% With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
  • 62
  • [ 402-43-7 ]
  • [ 125486-96-6 ]
  • [ 1045771-55-8 ]
YieldReaction ConditionsOperation in experiment
97% With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
  • 63
  • [ 69038-74-0 ]
  • [ 125486-96-6 ]
  • [ 1045771-49-0 ]
  • 64
  • [ 67832-11-5 ]
  • [ 125486-96-6 ]
  • [ 1045771-54-7 ]
YieldReaction ConditionsOperation in experiment
91% With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
  • 65
  • [ 139102-34-4 ]
  • [ 125486-96-6 ]
  • [ 1045771-51-4 ]
  • 66
  • [ 125486-96-6 ]
  • [ 104-88-1 ]
  • [ 1045771-44-5 ]
YieldReaction ConditionsOperation in experiment
88% With caesium carbonate In 1,4-dioxane at 120℃; for 15h;
  • 67
  • [ 125486-96-6 ]
  • [ 99-91-2 ]
  • [ 1045771-59-2 ]
YieldReaction ConditionsOperation in experiment
92% With caesium carbonate In 1,4-dioxane at 120℃; for 15h;
  • 68
  • [ 125486-96-6 ]
  • [ 105942-08-3 ]
  • [ 1045771-52-5 ]
YieldReaction ConditionsOperation in experiment
95% With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
  • 69
  • [ 125486-96-6 ]
  • [ 1122-91-4 ]
  • [ 1045771-44-5 ]
YieldReaction ConditionsOperation in experiment
90% With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
  • 70
  • [ 125486-96-6 ]
  • [ 6630-33-7 ]
  • [ 1045771-45-6 ]
YieldReaction ConditionsOperation in experiment
80% With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
  • 71
  • [ 125486-96-6 ]
  • [ 10298-80-3 ]
  • [ 1045771-65-0 ]
YieldReaction ConditionsOperation in experiment
74% With caesium carbonate In 1,4-dioxane at 120℃; for 15h;
  • 72
  • [ 1041262-63-8 ]
  • [ 125486-96-6 ]
  • C22H28N2O6SSi [ No CAS ]
  • [ 1041262-65-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)-1-(phenylthio)cyclohex-3-enecarboxylate With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In toluene at 0℃; for 2h; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 60℃; for 5h; Stage #3: 2-(trimethylsilyl)ethanesulfonamide With tetrakis(actonitrile)copper(I) hexafluorophosphate; iodosylbenzene; 3 A molecular sieve In acetonitrile at 20℃; Further stages. Title compound not separated from byproducts.;
Stage #1: ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)-1-(phenylthio)cyclohex-3-enecarboxylate With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In toluene at 0℃; for 2h; Inert atmosphere; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 60℃; for 5h; Inert atmosphere; Stage #3: 2-(trimethylsilyl)ethanesulfonamide With tetrakis(actonitrile)copper(I) hexafluorophosphate; iodosylbenzene In acetonitrile at 20℃; Inert atmosphere; Molecular sieve;
  • 73
  • [ 1041262-63-8 ]
  • [ 125486-96-6 ]
  • [ 1041262-65-0 ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)-1-(phenylthio)cyclohex-3-enecarboxylate With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In toluene at 0℃; for 2h; Inert atmosphere; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 60℃; for 5h; Inert atmosphere; Stage #3: 2-(trimethylsilyl)ethanesulfonamide With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]; bis(tertbutylcarbonyloxy)iodobenzene; magnesium oxide In chlorobenzene at 0 - 20℃; Inert atmosphere;
206 mg Stage #1: ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)-1-(phenylthio)cyclohex-3-enecarboxylate With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In toluene at 0℃; for 2h; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 60℃; for 5h; Stage #3: 2-(trimethylsilyl)ethanesulfonamide With magnesium oxide In chlorobenzene at 0 - 20℃; Further stages.;
  • 74
  • [ 125486-96-6 ]
  • [ 100-51-6 ]
  • [ 106018-87-5 ]
YieldReaction ConditionsOperation in experiment
95% With Ru/Fe3O4; potassium carbonate at 150℃; for 12h; Inert atmosphere;
94% With air; copper diacetate; potassium carbonate at 150℃; for 12h;
94% With copper diacetate; potassium carbonate at 150℃; for 12h;
87% With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; potassium carbonate; triphenylphosphine In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; for 24h; Inert atmosphere;

  • 75
  • [ 125486-96-6 ]
  • [ 124754-47-8 ]
  • (4S)-4-[(1-[2-(trimethylsilyl)ethanesulfonyl]-2-aziridinyl)methyl]-1,3-oxazolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With tetrakis(actonitrile)copper(I) hexafluorophosphate; iodosylbenzene In acetonitrile at 20℃; Molecular sieve; optical yield given as %de;
  • 76
  • [ 500-22-1 ]
  • [ 125486-96-6 ]
  • [ 1232688-60-6 ]
YieldReaction ConditionsOperation in experiment
With boron trifluoride diethyl etherate In toluene for 20h; Inert atmosphere; Reflux; Dean-Stark trap; 8.L.1 Step 1 Step 1 2-Trimethylsilyl-ethanesulfonic acid pyridin-3-ylmethyleneamide To a solution of 3-formylpyridine (0.228 mL, 2.42 mmol) and 2-(trimethylsilyl)ethanesulfonamide (0.438 g, 2.42 mmol) in toluene (30 mL) was added boron trifluoride etherate (0.02 mL, 0.15 mmol) under Ar. The mixture was heated at reflux for 20 hours using a Dean-Stark trap. After cooling, 10% aqueous sodium bicarbonate was added, and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated to dryness to under reduced pressure obtain crude 2-trimethylsilyl-ethanesulfonic acid pyridin-3-ylmethyleneamide (669 mg), which was used directly in the next step.
  • 77
  • [ 66236-13-3 ]
  • [ 125486-96-6 ]
  • [ 1251853-89-0 ]
YieldReaction ConditionsOperation in experiment
80% With manganese(IV) oxide; 2,6-di-tert-butyl-4-methylpyridine; copper(II) 2-ethylhexanoate In α,α,α-trifluorotoluene at 20 - 110℃; for 24.3333h; Inert atmosphere; Molecular sieve;
  • 78
  • [ 125486-96-6 ]
  • [ 642-31-9 ]
  • N-(9-anthrylmethylidene)-2-trimethylsilylethanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With boron trifluoride diethyl etherate In toluene at 110℃; for 5h; Inert atmosphere; Dean-Stark separator;
  • 79
  • [ 100-13-0 ]
  • [ 125486-96-6 ]
  • [ 1276115-46-8 ]
YieldReaction ConditionsOperation in experiment
82% Stage #1: 2-(trimethylsilyl)ethanesulfonamide With water; pivaloyl chloride; sodium hydroxide at 20℃; for 1h; Stage #2: 4-nitrostyrene With iodine at 20℃; for 1h;
  • 80
  • [ 7642-09-3 ]
  • [ 125486-96-6 ]
  • (3R,4R)-3-iodo-4-(2-(trimethylsilyl)ethylsulfonamido)hexane [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% Stage #1: 2-(trimethylsilyl)ethanesulfonamide With water; pivaloyl chloride; sodium hydroxide In dichloromethane at 20℃; for 1h; Stage #2: cis-3-hexene In dichloromethane at 20℃; for 1h;
  • 81
  • [ 125486-96-6 ]
  • [ 140-88-5 ]
  • [ 1276115-48-0 ]
YieldReaction ConditionsOperation in experiment
73% Stage #1: 2-(trimethylsilyl)ethanesulfonamide With water; pivaloyl chloride; sodium hydroxide at 20℃; for 1h; Stage #2: ethyl acrylate With iodine at 20℃; for 1h;
  • 82
  • [ 1282041-44-4 ]
  • [ 125486-96-6 ]
  • [ 1282041-45-5 ]
YieldReaction ConditionsOperation in experiment
49% With I(sym-coll)2ClO4 In dichloromethane at 0℃; for 2h; Molecular sieve; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
  • 83
  • [ 51450-24-9 ]
  • [ 125486-96-6 ]
  • [ 1293911-24-6 ]
YieldReaction ConditionsOperation in experiment
85% With iodine In dichloromethane at -10℃; for 0.5h; Molecular sieve;
  • 84
  • [ 51450-24-9 ]
  • [ 125486-96-6 ]
  • 3,6-di-O-acetyl-1,2-dideoxy-2-iodo-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-[2-(trimethylsilyl)ethanesulfonamido]-α-D-mannopyranose [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: hexa-O-acetyl-D-lactal; 2-(trimethylsilyl)ethanesulfonamide With N-iodo-succinimide In dichloromethane at -10℃; for 2h; Molecular sieve; Stage #2: With iodine In dichloromethane at -10 - 5℃; Molecular sieve; diastereoselective reaction;
  • 85
  • [ 51450-24-9 ]
  • [ 125486-96-6 ]
  • 3,6-di-O-acetyl-1,2-dideoxy-2-iodo-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-[2-(trimethylsilyl)ethanesulfonamido]-β-D-mannopyranose [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With Iodine monochloride In dichloromethane at -10℃; for 2.5h; Molecular sieve;
  • 86
  • [ 13322-90-2 ]
  • [ 125486-96-6 ]
  • [ 1293911-34-8 ]
  • 87
  • [ 13322-90-2 ]
  • [ 125486-96-6 ]
  • [ 1293911-38-2 ]
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