Alternatived Products of [ 125486-96-6 ]
Product Details of [ 125486-96-6 ]
CAS No. : 125486-96-6
MDL No. : MFCD09265152
Formula :
C5 H15 NO2 SSi
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 ]
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 ]
1
[ 125486-96-6 ]
[ 142800-35-9 ]
[ 143544-41-6 ]
Yield Reaction Conditions Operation in experiment
82%
With iodonium(di-γ-collidine) perchlorate In dichloromethane
82%
With iodonium(di-γ-collidine) perchlorate In dichloromethane at 0℃; for 0.5h;
Reference:
[1]Danishefsky, Samuel J.; Koseki, Koshi; Griffith, David A.; Gervay, Jacquelyn; Peterson, John M.; et al.
[Journal of the American Chemical Society, 1992, vol. 114, # 21, p. 8331 - 8333]
[2]Danishefsky, Samuel J.; Gervay, Jacquelyn; Peterson, John M.; McDonald, Frank E.; Koseki, Koshi; Griffith, David A.; Oriyama, Takeshi; Marsden, Stephen P.
[Journal of the American Chemical Society, 1995, vol. 117, # 7, p. 1940 - 1953]
2
[ 125486-96-6 ]
[ 115534-34-4 ]
Yield Reaction Conditions Operation in experiment
With N,N-dichloro-p-toluenesulfonamide; thionyl chloride In benzene for 28h; Heating;
With thionyl chloride In benzene for 48h; Heating;
Reference:
[1]Garigipati; Tschaen; Weinreb
[Journal of the American Chemical Society, 1990, vol. 112, # 9, p. 3475 - 3482]
[2]Sisko, Joseph; Weinreb, Steven M.
[Journal of Organic Chemistry, 1990, vol. 55, # 1, p. 393 - 395]
[3]Schleusner, Marcel; Gais, Hans-Joachim; Koep, Stefan; Raabe, Gerhard
[Journal of the American Chemical Society, 2002, vol. 124, # 26, p. 7789 - 7800]
3
[ 55628-54-1 ]
[ 125486-96-6 ]
[ 183989-07-3 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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℃;
Reference:
[1]Wang, Zhi-Guang; Zhang, Xufang; Visser, Michael; Live, David; Zatorski, Andrzej; Iserloh, Ulrich; Lloyd, Kenneth O.; Danishefsky, Samuel J.
[Angewandte Chemie - International Edition, 2001, vol. 40, # 9, p. 1728 - 1732]
8
[ 100-42-5 ]
[ 125486-96-6 ]
[ 236122-14-8 ]
Yield Reaction Conditions Operation 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;
Reference:
[1]Minakata, Satoshi; Morino, Yoshinobu; Oderaotoshi, Yoji; Komatsu, Mitsuo
[Chemical Communications, 2006, # 31, p. 3337 - 3339]
[2]Dauban; Saniere; Tarrade; Dodd
[Journal of the American Chemical Society, 2001, vol. 123, # 31, p. 7707 - 7708]
9
[ 498-66-8 ]
[ 125486-96-6 ]
3-(2-trimethylsilanyl-ethanesulfonyl)-3-aza-tricyclo[3.2.1.02,4 ]octane
[ No CAS ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation in experiment
69%
With boron trifluoride diethyl etherate In toluene for 3h; Heating;
15
[ 5414-21-1 ]
[ 125486-96-6 ]
[ 652130-73-9 ]
Yield Reaction Conditions Operation in experiment
76%
With caesium carbonate In N,N-dimethyl-formamide at 20℃;
16
[ 6621-59-6 ]
[ 125486-96-6 ]
[ 652130-74-0 ]
Yield Reaction Conditions Operation in experiment
73%
With caesium carbonate In N,N-dimethyl-formamide at 20℃;
17
[ 106018-85-3 ]
[ 125486-96-6 ]
Yield Reaction Conditions Operation in experiment
88%
With ammonia In dichloromethane at 0℃; for 2h;
75%
With ammonium hydroxide In water; acetonitrile at 0 - 20℃;
31%
With ethanol; ammonia In dichloromethane at 0℃;
Reference:
[1]Parker, Laurie L.; Gowans, Nicholas D.; Jones, Stephen W.; Robins, David J.
[Tetrahedron, 2003, vol. 59, # 51, p. 10165 - 10171]
[2]Benohoud, Meryem; Leman, Loic; Cardoso, Silvia H.; Retailleau, Pascal; Dauban, Philippe; Thierry, Josiane; Dodd, Robert H.
[Journal of Organic Chemistry, 2009, vol. 74, # 15, p. 5331 - 5336]
[3]Aggarwal; Ferrara; O'Brien; Thompson; Jones; Fieldhouse
[Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 14, p. 1635 - 1643]
18
[ 500-22-1 ]
[ 125486-96-6 ]
[ 292638-85-8 ]
methyl 2-(pyridin-3-yl(2-(trimethylsilyl)ethylsulfonamido)methyl)acrylate
[ No CAS ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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;
24
[ 125486-96-6 ]
[ 100-52-7 ]
[ 292638-85-8 ]
[ 816457-61-1 ]
Yield Reaction Conditions Operation in experiment
86%
With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 70℃; for 10h;
Reference:
[1]Declerck, Valerie; Ribiere, Patrice; Martinez, Jean; Lamaty, Fredereric
[Journal of Organic Chemistry, 2004, vol. 69, # 24, p. 8372 - 8381]
[2]Ribière, Patrice; Declerck, Valérie; Nédellec, Yannig; Yadav-Bhatnagar, Neerja; Martinez, Jean; Lamaty, Frédéric
[Tetrahedron, 2006, vol. 62, # 44, p. 10456 - 10466]
[3]Declerck, Valerie; Allouchi, Hassan; Martinez, Jean; Lamaty, Frederic
[Journal of Organic Chemistry, 2007, vol. 72, # 4, p. 1518 - 1521]
25
[ 125486-96-6 ]
[ 66-99-9 ]
[ 292638-85-8 ]
[ 816457-67-7 ]
Yield Reaction Conditions Operation in experiment
60%
With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 70℃; for 48h;
Reference:
[1]Declerck, Valerie; Ribiere, Patrice; Martinez, Jean; Lamaty, Fredereric
[Journal of Organic Chemistry, 2004, vol. 69, # 24, p. 8372 - 8381]
[2]Declerck, Valerie; Allouchi, Hassan; Martinez, Jean; Lamaty, Frederic
[Journal of Organic Chemistry, 2007, vol. 72, # 4, p. 1518 - 1521]
26
[ 26260-02-6 ]
[ 125486-96-6 ]
[ 292638-85-8 ]
[ 816457-72-4 ]
Yield Reaction Conditions Operation in experiment
73%
With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 70℃; for 10h;
Reference:
[1]Declerck, Valerie; Ribiere, Patrice; Martinez, Jean; Lamaty, Fredereric
[Journal of Organic Chemistry, 2004, vol. 69, # 24, p. 8372 - 8381]
[2]Declerck, Valerie; Allouchi, Hassan; Martinez, Jean; Lamaty, Frederic
[Journal of Organic Chemistry, 2007, vol. 72, # 4, p. 1518 - 1521]
27
[ 5779-95-3 ]
[ 125486-96-6 ]
[ 292638-85-8 ]
[ 816457-69-9 ]
Yield Reaction Conditions Operation in experiment
70%
With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 70℃; for 72h;
28
[ 7311-34-4 ]
[ 125486-96-6 ]
[ 292638-85-8 ]
[ 816457-62-2 ]
Yield Reaction Conditions Operation in experiment
67%
With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 70℃; for 72h;
Reference:
[1]Declerck, Valerie; Ribiere, Patrice; Martinez, Jean; Lamaty, Fredereric
[Journal of Organic Chemistry, 2004, vol. 69, # 24, p. 8372 - 8381]
[2]Ribière, Patrice; Declerck, Valérie; Nédellec, Yannig; Yadav-Bhatnagar, Neerja; Martinez, Jean; Lamaty, Frédéric
[Tetrahedron, 2006, vol. 62, # 44, p. 10456 - 10466]
[3]Declerck, Valerie; Allouchi, Hassan; Martinez, Jean; Lamaty, Frederic
[Journal of Organic Chemistry, 2007, vol. 72, # 4, p. 1518 - 1521]
29
[ 125486-96-6 ]
[ 77123-57-0 ]
[ 292638-85-8 ]
[ 816457-73-5 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation in experiment
79%
With 1,4-diaza-bicyclo[2.2.2]octane In isopropyl alcohol at 70℃; for 6h;
Reference:
[1]Declerck, Valerie; Ribiere, Patrice; Martinez, Jean; Lamaty, Fredereric
[Journal of Organic Chemistry, 2004, vol. 69, # 24, p. 8372 - 8381]
[2]Declerck, Valerie; Allouchi, Hassan; Martinez, Jean; Lamaty, Frederic
[Journal of Organic Chemistry, 2007, vol. 72, # 4, p. 1518 - 1521]
34
[ 24424-99-5 ]
[ 125486-96-6 ]
[ 145387-82-2 ]
Yield Reaction Conditions Operation in experiment
90%
With dmap; triethylamine In dichloromethane at 20℃;
35
[ 1193-82-4 ]
[ 125486-96-6 ]
[ 452898-05-4 ]
Yield Reaction Conditions Operation 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;
Reference:
[1]Gae, Young Cho; Bolm, Carsten
[Organic Letters, 2005, vol. 7, # 22, p. 4983 - 4985]
[2]Mancheno, Olga Garcia; Dallimore, Jonathan; Plant, Andrew; Bolm, Carsten
[Organic Letters, 2009, vol. 11, # 11, p. 2429 - 2432]
[3]Mancheno, Olga Garcia; Bolm, Carsten
[Organic Letters, 2006, vol. 8, # 11, p. 2349 - 2352]
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 ]
Yield Reaction Conditions Operation 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;
Reference:
[1]Wang, Zhi-Guang; Warren, J. David; Dudkin, Vadim Y.; Zhang, Xufang; Iserloh, Ulrich; Visser, Michael; Eckhardt, Matthias; Seeberger, Peter H.; Danishefsky, Samuel J.
[Tetrahedron, 2006, vol. 62, # 20, p. 4954 - 4978]
37
[ 125486-96-6 ]
[ 292638-85-8 ]
[ 105-07-7 ]
[ 929012-64-6 ]
Yield Reaction Conditions Operation 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 ]
C10 H21 NO4 SSi
[ No CAS ]
Yield Reaction Conditions Operation in experiment
93%
With toluene-4-sulfonic acid In benzene Heating;
39
C12 H20 O3
[ No CAS ]
[ 125486-96-6 ]
C17 H33 NO4 SSiH2 O
[ No CAS ]
Yield Reaction Conditions Operation in experiment
85%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 48h;
40
[ 125486-96-6 ]
[ 212071-06-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: potassium carbonate / dimethylformamide
2: 2nd generation Grubbs catalyst / CH2 Cl2
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 / K2 CO3 / dimethylformamide / 6 h / 20 °C
3: 98 percent / Cl2 (PCyhex3 )(N1 ,N3 -dimesyl-imidazol-2-yl)benzylidene Ru(VI) / CH2 Cl2 / 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
Reference:
[1]Declerck, Valerie; Allouchi, Hassan; Martinez, Jean; Lamaty, Frederic
[Journal of Organic Chemistry, 2007, vol. 72, # 4, p. 1518 - 1521]
[2]Declerck, Valerie; Ribiere, Patrice; Martinez, Jean; Lamaty, Fredereric
[Journal of Organic Chemistry, 2004, vol. 69, # 24, p. 8372 - 8381]
[3]Xu, Zhenrong; Lu, Xiyan
[Journal of Organic Chemistry, 1998, vol. 63, # 15, p. 5031 - 5041]
41
[ 125486-96-6 ]
[ 223581-87-1 ]
Yield Reaction Conditions Operation 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 *(CH3 CN)2 / CH2 Cl2
Reference:
[1]Ferraris; Young; Cox; Dudding; Drury III; Ryzhkov; Taggi; Lectka
[Journal of the American Chemical Society, 2002, vol. 124, # 1, p. 67 - 77]
[2]Ferraris, Dana; Young, Brandon; Dudding, Travis; Drury III, William J.; Lectka, Thomas
[Tetrahedron, 1999, vol. 55, # 29, p. 8869 - 8882]
42
1-(p-methoxyphenyl)ethyl acetate
[ No CAS ]
[ 125486-96-6 ]
[ 1025359-75-4 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation in experiment
84%
With caesium carbonate In 1,4-dioxane at 120℃; for 15h;
44
[ 109-09-1 ]
[ 125486-96-6 ]
[ 1045771-58-1 ]
Yield Reaction Conditions Operation in experiment
67%
With caesium carbonate In 1,4-dioxane at 120℃; for 15h;
45
[ 109-04-6 ]
[ 125486-96-6 ]
[ 1045771-58-1 ]
Yield Reaction Conditions Operation in experiment
85%
With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
46
[ 1722-12-9 ]
[ 125486-96-6 ]
[ 1045771-69-4 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation in experiment
80%
With caesium carbonate In 1,4-dioxane at 120℃; for 15h;
49
[ 39856-50-3 ]
[ 125486-96-6 ]
[ 1045771-57-0 ]
Yield Reaction Conditions Operation in experiment
85%
With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
50
[ 108-86-1 ]
[ 125486-96-6 ]
[ 1045771-47-8 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation in experiment
88%
With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
57
[ 24398-88-7 ]
[ 125486-96-6 ]
[ 1045771-48-9 ]
Yield Reaction Conditions Operation in experiment
95%
With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
58
[ 5798-75-4 ]
[ 125486-96-6 ]
[ 1045771-43-4 ]
Yield Reaction Conditions Operation in experiment
98%
With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
59
[ 90-11-9 ]
[ 125486-96-6 ]
[ 1045771-56-9 ]
Yield Reaction Conditions Operation in experiment
82%
With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
60
[ 623-00-7 ]
[ 125486-96-6 ]
[ 1045771-46-7 ]
Yield Reaction Conditions Operation in experiment
91%
With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
61
[ 577-19-5 ]
[ 125486-96-6 ]
[ 1045771-53-6 ]
Yield Reaction Conditions Operation in experiment
85%
With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
62
[ 402-43-7 ]
[ 125486-96-6 ]
[ 1045771-55-8 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation in experiment
88%
With caesium carbonate In 1,4-dioxane at 120℃; for 15h;
67
[ 125486-96-6 ]
[ 99-91-2 ]
[ 1045771-59-2 ]
Yield Reaction Conditions Operation in experiment
92%
With caesium carbonate In 1,4-dioxane at 120℃; for 15h;
68
[ 125486-96-6 ]
[ 105942-08-3 ]
[ 1045771-52-5 ]
Yield Reaction Conditions Operation in experiment
95%
With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
69
[ 125486-96-6 ]
[ 1122-91-4 ]
[ 1045771-44-5 ]
Yield Reaction Conditions Operation in experiment
90%
With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
70
[ 125486-96-6 ]
[ 6630-33-7 ]
[ 1045771-45-6 ]
Yield Reaction Conditions Operation in experiment
80%
With caesium carbonate In 1,4-dioxane at 100℃; for 15h;
71
[ 125486-96-6 ]
[ 10298-80-3 ]
[ 1045771-65-0 ]
Yield Reaction Conditions Operation in experiment
74%
With caesium carbonate In 1,4-dioxane at 120℃; for 15h;
72
[ 1041262-63-8 ]
[ 125486-96-6 ]
C22 H28 N2 O6 SSi
[ No CAS ]
[ 1041262-65-0 ]
Yield Reaction Conditions Operation 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;
Reference:
[1]Trost, Barry M.; Zhang, Ting
[Angewandte Chemie - International Edition, 2008, vol. 47, # 20, p. 3759 - 3761]
[2]Location in patent: experimental part
Trost, Barry M.; Zhang, Ting
[Chemistry - A European Journal, 2011, vol. 17, # 13, p. 3630 - 3643]
73
[ 1041262-63-8 ]
[ 125486-96-6 ]
[ 1041262-65-0 ]
Yield Reaction Conditions Operation 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.;
Reference:
[1]Trost, Barry M.; Zhang, Ting
[Chemistry - A European Journal, 2011, vol. 17, # 13, p. 3630 - 3643]
[2]Trost, Barry M.; Zhang, Ting
[Angewandte Chemie - International Edition, 2008, vol. 47, # 20, p. 3759 - 3761]
74
[ 125486-96-6 ]
[ 100-51-6 ]
[ 106018-87-5 ]
Yield Reaction Conditions Operation in experiment
95%
With Ru/Fe3 O4 ; 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;
Reference:
[1]Shi, Feng; Tse, Man Kin; Zhou, Shaolin; Pohl, Marga-Martina; Radnik, Joerg; et al.
[Journal of the American Chemical Society, 2009, vol. 131, p. 1775 - 1779]
[2]Shi, Feng; Tse, Man Kin; Cui, Xinjiang; Goerdes, Dirk; Michalik, Dirk; Thurow, Kerstin; Deng, Youquan; Beller, Matthias
[Angewandte Chemie - International Edition, 2009, vol. 48, # 32, p. 5912 - 5915]
[3]Location in patent: scheme or table
Cui, Xinjiang; Shi, Feng; Tse, Man Kin; Goerdes, Dirk; Thurow, Kerstin; Beller, Matthias; Deng, Youquan
[Advanced Synthesis and Catalysis, 2009, vol. 351, # 17, p. 2949 - 2958]
[4]Location in patent: experimental part
Lamb, Gareth W.; Watson, Andrew J.A.; Jolley, Katherine E.; Maxwell, Aoife C.; Williams, Jonathan M.J.
[Tetrahedron Letters, 2009, vol. 50, # 26, p. 3374 - 3377]
75
[ 125486-96-6 ]
[ 124754-47-8 ]
(4S)-4-[(1-[2-(trimethylsilyl)ethanesulfonyl]-2-aziridinyl)methyl]-1,3-oxazolidin-2-one
[ No CAS ]
Yield Reaction Conditions Operation in experiment
45%
With tetrakis(actonitrile)copper(I) hexafluorophosphate; iodosylbenzene In acetonitrile at 20℃; Molecular sieve; optical yield given as %de;
Reference:
[1]Location in patent: experimental part
Benohoud, Meryem; Leman, Loic; Cardoso, Silvia H.; Retailleau, Pascal; Dauban, Philippe; Thierry, Josiane; Dodd, Robert H.
[Journal of Organic Chemistry, 2009, vol. 74, # 15, p. 5331 - 5336]
76
[ 500-22-1 ]
[ 125486-96-6 ]
[ 1232688-60-6 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]
Yield Reaction Conditions Operation 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 ]