[ CAS No. 80522-42-5 ] {[proInfo.proName]}

Name: 80522-42-5|Triisopropylsilyl trifluoromethanesulfonate|97% T
Brand: Ambeed
SKU: A274403
Price: 5.0 USD
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Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 80522-42-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 80522-42-5 ]

SDS Specification

Alternatived Products of [ 80522-42-5 ]

Product Details of [ 80522-42-5 ]

CAS No. :	80522-42-5	MDL No. :	MFCD00009913
Formula :	C₁₀H₂₁F₃O₃SSi	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LHJCZOXMCGQVDQ-UHFFFAOYSA-N
M.W :	306.42	Pubchem ID :	2724529
Synonyms :

Calculated chemistry of [ 80522-42-5 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	6
Num. H-bond acceptors :	6.0
Num. H-bond donors :	0.0
Molar Refractivity :	68.29
TPSA :	51.75 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.5 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.04
Log Po/w (XLOGP3) :	5.17
Log Po/w (WLOGP) :	6.37
Log Po/w (MLOGP) :	2.84
Log Po/w (SILICOS-IT) :	1.07
Consensus Log Po/w :	3.7

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.6
Solubility :	0.00768 mg/ml ; 0.0000251 mol/l
Class :	Moderately soluble
Log S (Ali) :	-6.0
Solubility :	0.000304 mg/ml ; 0.000000993 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-2.99
Solubility :	0.312 mg/ml ; 0.00102 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.26

Safety of [ 80522-42-5 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P264-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P363-P405-P501	UN#:	3265
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 80522-42-5 ]

* 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.

Upstream synthesis route of [ 80522-42-5 ]
Downstream synthetic route of [ 80522-42-5 ]

[ 80522-42-5 ] Synthesis Path-Upstream 1~3

1
[ 6485-79-6 ]
[ 1493-13-6 ]
[ 80522-42-5 ]

Reference： [1] Tetrahedron Letters, 1981, vol. 22, # 36, p. 3455 - 3458
[2] Advanced Synthesis and Catalysis, 2009, vol. 351, # 7-8, p. 1035 - 1040
[3] European Journal of Organic Chemistry, 2017, vol. 2017, # 17, p. 2512 - 2539
[4] European Journal of Organic Chemistry, 2017, vol. 2017, # 20, p. 2883 - 2915

2
[ 1493-13-6 ]
[ 24400-84-8 ]
[ 80522-42-5 ]

Reference： [1] Synthesis, 1997, # 7, p. 744 - 746

3
[ 13154-24-0 ]
[ 1493-13-6 ]
[ 80522-42-5 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1990, vol. 63, # 4, p. 1039 - 1048
[2] Tetrahedron Letters, 1987, vol. 28, # 49, p. 6191 - 6194

[ 80522-42-5 ] Synthesis Path-Downstream 1~88

1
[ 6881-49-8 ]
[ 80522-42-5 ]
[ 137812-10-3 ]

Reference： [1]Canadian Journal of Chemistry,1991,vol. 69,p. 1487 - 1497

2
[ 6710-62-9 ]
[ 16075-82-4 ]
[ 80522-42-5 ]
[ 133721-57-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	With di(tert-butyl)pyridine In chloroform at 0℃; for 2h; other 2,2-dialkyl-2,3-dihydro-4H-pyranones, other acetylenes, other trialkylsilyltriflates;
95%	With di(tert-butyl)pyridine In chloroform at 0℃; for 2h;

Reference： [1]Obrecht, Daniel [Helvetica Chimica Acta, 1991, vol. 74, # 1, p. 27 - 46]
[2]Obrecht, Daniel [Helvetica Chimica Acta, 1991, vol. 74, # 1, p. 27 - 46]

3
[ 69778-83-2 ]
[ 80522-42-5 ]
[ 109826-87-1 ]

Reference： [1]Tetrahedron Letters,1986,vol. 27,p. 5285 - 5288

4
[ 10150-93-3 ]
[ 80522-42-5 ]
[ 145106-32-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: (E)-ethyl 4-oxo-2-pentenoate With triethylamine In diethyl ether at 0℃; for 0.166667h; Inert atmosphere; Stage #2: triisopropylsilyl trifluoromethanesulfonate In diethyl ether at 0℃; for 2.5h; Inert atmosphere;
96%	With triethylamine In diethyl ether

Reference： [1]Abbasov, Mikail E.; Hudson, Brandi M.; Tantillo, Dean J.; Romo, Daniel [Journal of the American Chemical Society, 2014, vol. 136, # 12, p. 4492 - 4495]
[2]Page, Philip C. Bulman; Jennens, David C. [Journal of the Chemical Society. Perkin transactions I, 1992, # 20, p. 2587 - 2589]

5
[ 53562-86-0 ]
[ 80522-42-5 ]
[ 126249-06-7 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-dimethylpyridine
	With 2,6-dimethylpyridine In dichloromethane at 0 - 25℃; for 4h; Inert atmosphere;

Reference： [1]Rychnovsky, Scott D.; Skalitzky, Donald J.; Pathirana, Charles; Jensen, Paul R.; Fenical, William [Journal of the American Chemical Society, 1992, vol. 114, # 2, p. 671 - 677]
[2]Anderson, Katie; Calo, Frederick; Pfaffeneder, Toni; White, Andrew J. P.; Barrett, Anthony G. M. [Organic Letters, 2011, vol. 13, # 21, p. 5748 - 5750]

6
[ 4529-04-8 ]
[ 80522-42-5 ]
[ 82192-57-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	In diethyl ether at -40 - 0℃;

Reference： [1]Corey, E. J.; Ruecker, Cristoph [Tetrahedron Letters, 1982, vol. 23, # 7, p. 719 - 722]

7
[ 80522-42-5 ]
[ 104987-11-3 ]
[ 123747-39-7 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 5451 - 5454

8
[ 80522-42-5 ]
[ 3976-69-0 ]
methyl 3(R)-<<tris(1-methylethyl)silyl>oxy>butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With 2,6-dimethylpyridine for 3h; Ambient temperature;
95%	With 2,6-dimethylpyridine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;

Reference： [1]Lynch, Joseph E.; Riseman, Stephen M.; Laswell, William L.; Tschaen, David M.; Volante, Ralph P.; et al. [Journal of Organic Chemistry, 1989, vol. 54, # 16, p. 3792 - 3796]
[2]Burghart-Stoll, Heike; Brueckner, Reinhard [European Journal of Organic Chemistry, 2012, # 21, p. 3978 - 4017]

9
[ 80522-42-5 ]
[ 53123-88-9 ]
[ 151122-98-4 ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 962 - 973
[2]Tetrahedron Letters,1992,vol. 33,p. 7469 - 7472

10
[ 80522-42-5 ]
[ 3102-33-8 ]
[ 134745-26-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: trans-3-penten-2-one With triethylamine In dichloromethane at 0℃; for 0.0833333h; Stage #2: triisopropylsilyl trifluoromethanesulfonate In dichloromethane for 0.5h;
86%	With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
72%	With 2,6-dimethylpyridine In tetrahydrofuran at 0 - 25℃;

	With potassium hexamethylsilazane 1.) toluene, THF, -78 deg C, 1 h, 2.) toluene, THF, from -78 deg C to -40 deg C, 1 h; Yield given. Multistep reaction;
	With triethylamine
	Stage #1: trans-3-penten-2-one With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: triisopropylsilyl trifluoromethanesulfonate In tetrahydrofuran; hexane at -78 - 20℃;

Reference： [1]Davies, Huw M. L.; Zhang, Bowen [Angewandte Chemie - International Edition, 2020, vol. 59, # 12, p. 4937 - 4941][Angew. Chem., 2020, vol. 132, # 12, p. 4967 - 4971,5]
[2]Guzmn, Pablo E.; Lian, Yajing; Davies, Huw M. L. [Angewandte Chemie - International Edition, 2014, vol. 53, # 48, p. 13083 - 13087][Angew. Chem., 2014, vol. 126, # 48, p. 13299 - 13303,5]
[3]Rahm, Annette; Rheingold, Arnold L.; Wulff, William D. [Tetrahedron, 2000, vol. 56, # 28, p. 4951 - 4965]
[4]Jacobi, Peter A.; Cai, Guolin [Heterocycles, 1993, vol. 35, # 2, p. 1103 - 1120]
[5]Oppolzer, Wolfgang; Seletsky, Boris M.; Bernardinelli, Gerald [Tetrahedron Letters, 1994, vol. 35, # 21, p. 3509 - 3512]
[6]Nakashima, Daisuke; Yamamoto, Hisashi [Journal of the American Chemical Society, 2006, vol. 128, # 30, p. 9626 - 9627]

11
[ 69125-55-9 ]
[ 80522-42-5 ]
Triisopropyl-(4-methoxy-cyclohex-3-enyloxy)-silane [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1994,vol. 59,p. 6955 - 6964
[2]Journal of the American Chemical Society,2012,vol. 134,p. 18944 - 18947

12
[ 51731-17-0 ]
[ 80522-42-5 ]
[ 163811-52-7 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane
	With triethylamine In diethyl ether at -20 - 0℃; for 2h;

Reference： [1]Beifuss, Uwe; Gehm, Henning; Noltemeyer, Mathias; Schmidt, Hans-Georg [Angewandte Chemie, 1995, vol. 107, # 6, p. 705 - 707]
[2]Zhao, Bei; Loh, Teck-Peng [Organic Letters, 2013, vol. 15, # 12, p. 2914 - 2917]

13
[ 623-15-4 ]
[ 80522-42-5 ]
(E)-((4-(furan-2-yl)buta-1,3-dien-2-yl)oxy)triisopropylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With triethylamine In tetrahydrofuran at 0℃; for 2.5h; Inert atmosphere; Schlenk technique;	General Procedure for the Synthesis of Dienes 2a-m General procedure: Similar to the reported procedure[2], in a dry argon flushed Schlenk-flask the ,-unsaturatedketone (1.0 eq.) are dissolved in dry THF and cooled to 0 °C for 15 min. Subsequently dryEt3N (2.4 eq.) and TIPSOTf (1.1 eq.) are added slowly. After 2.5 h at 0 °C the reaction isquenched by adding Et3N (4.0 eq.) and diluted with n-hexane. The organic phase is washedwith sat. NH4Cl(aq) (3x), water (3x) and brine. The solvent is evaporated and the crude productis purified by filtration through a silica plug with a mixture of n-pentane:Et2O (50:1) as aneluent. The products are obtained as oils.
	In dichloromethane

Reference： [1]Beceño, Christian; Krappitz, Tim; Raabe, Gerhard; Enders, Dieter [Synthesis, 2015, vol. 47, # 23, p. 3813 - 3821]
[2]Beifuss, Uwe; Gehm, Henning; Noltemeyer, Mathias; Schmidt, Hans-Georg [Angewandte Chemie, 1995, vol. 107, # 6, p. 705 - 707]

14
[ 80522-42-5 ]
[ 1896-62-4 ]
[ 163811-53-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine In dichloromethane at 0 - 20℃; for 8h; Inert atmosphere;
88%	With triethylamine In tetrahydrofuran at 0℃; for 2.5h; Inert atmosphere; Schlenk technique;	General Procedure for the Synthesis of Dienes 2a-m General procedure: Similar to the reported procedure[2], in a dry argon flushed Schlenk-flask the ,-unsaturatedketone (1.0 eq.) are dissolved in dry THF and cooled to 0 °C for 15 min. Subsequently dryEt3N (2.4 eq.) and TIPSOTf (1.1 eq.) are added slowly. After 2.5 h at 0 °C the reaction isquenched by adding Et3N (4.0 eq.) and diluted with n-hexane. The organic phase is washedwith sat. NH4Cl(aq) (3x), water (3x) and brine. The solvent is evaporated and the crude productis purified by filtration through a silica plug with a mixture of n-pentane:Et2O (50:1) as aneluent. The products are obtained as oils.
62%	With triethylamine In benzene at 20℃; for 2h;

In dichloromethane

Reference： [1]Racine, Sophie; Denanteuil, Florian; Serrano, Eloisa; Waser, Jerome [Angewandte Chemie - International Edition, 2014, vol. 53, # 32, p. 8484 - 8487][Angew. Chem., 2014, vol. 126, # 32, p. 8624 - 8627,4]
[2]Beceño, Christian; Krappitz, Tim; Raabe, Gerhard; Enders, Dieter [Synthesis, 2015, vol. 47, # 23, p. 3813 - 3821]
[3]Kimura, Masanari; Ezoe, Akihiro; Mori, Masahiko; Iwata, Keisuke; Tamaru, Yoshinao [Journal of the American Chemical Society, 2006, vol. 128, # 26, p. 8559 - 8568]
[4]Beifuss, Uwe; Gehm, Henning; Noltemeyer, Mathias; Schmidt, Hans-Georg [Angewandte Chemie, 1995, vol. 107, # 6, p. 705 - 707]

15
[ 80522-42-5 ]
[ 932-66-1 ]
[ 163811-58-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethylamine In tetrahydrofuran at 0℃; for 2h;
94%	With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
36%	With lithium diisopropyl amide In tetrahydrofuran at -78 - 20℃;

In dichloromethane

Reference： [1]Grant, Tina N.; West [Journal of the American Chemical Society, 2006, vol. 128, # 29, p. 9348 - 9349]
[2]Guzmn, Pablo E.; Lian, Yajing; Davies, Huw M. L. [Angewandte Chemie - International Edition, 2014, vol. 53, # 48, p. 13083 - 13087][Angew. Chem., 2014, vol. 126, # 48, p. 13299 - 13303,5]
[3]Rahm, Annette; Rheingold, Arnold L.; Wulff, William D. [Tetrahedron, 2000, vol. 56, # 28, p. 4951 - 4965]
[4]Beifuss, Uwe; Gehm, Henning; Noltemeyer, Mathias; Schmidt, Hans-Georg [Angewandte Chemie, 1995, vol. 107, # 6, p. 705 - 707]

16
[ 1120-72-5 ]
[ 80522-42-5 ]
[ 172605-59-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethylamine In dichloromethane for 0.166667h;
59%	With triethylamine In dichloromethane at 0℃;

Reference： [1]Yu, Jin-Quan; Wu, Hai-Chen; Corey [Organic Letters, 2005, vol. 7, # 7, p. 1415 - 1417]
[2]Magnus, Philip; Lacour, Jerome; Coldham, Iain; Mugrage, Benjamin; Bauta, William B. [Tetrahedron, 1995, vol. 51, # 41, p. 11087 - 11110]

17
[ 30434-64-1 ]
[ 80522-42-5 ]
[ 183385-32-2 ]

Reference： [1]Chemical Communications,1996,p. 2123 - 2124

18
[ 54458-61-6 ]
[ 80522-42-5 ]
[ 183385-44-6 ]

Reference： [1]Chemical Communications,1996,p. 2123 - 2124

19
[ 42116-44-9 ]
[ 80522-42-5 ]
[ 186375-61-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With triethylamine In dichloromethane 0 deg C, 5 min; 0 deg C to RT;
98%	With triethylamine In dichloromethane at 0 - 20℃;

Reference： [1]Roby, Johanne; Voyer, Normand [Tetrahedron Letters, 1997, vol. 38, # 2, p. 191 - 194]
[2]Barberis, Claude; Voyer, Normand; Roby, Johanne; Chénard, Sylvain; Tremblay, Martin; Labrie, Philippe [Tetrahedron, 2001, vol. 57, # 15, p. 2965 - 2972]

20
[ 2142-06-5 ]
[ 80522-42-5 ]
1-Benzyl-2,5-bis-triisopropylsilanyloxy-1H-pyrrole [ No CAS ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 2617 - 2620

21
[ 41167-74-2 ]
[ 80522-42-5 ]
[ 189579-26-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With triethylamine In dichloromethane for 2h; Ambient temperature;

Reference： [1]Martin, Stephen F.; Limberakis, Chris [Tetrahedron Letters, 1997, vol. 38, # 15, p. 2617 - 2620]

22
[ 80522-42-5 ]
[ 497-23-4 ]
[ 171201-21-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With triethylamine In dichloromethane at 0 - 20℃; for 2.5h; Inert atmosphere;
95%	With N-ethyl-N,N-diisopropylamine In dichloromethane 0 deg C to r.t.;
94%	With triethylamine In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere;

94%	With triethylamine In dichloromethane at 0 - 20℃; for 2h;
92%	With triethylamine In dichloromethane at 0 - 20℃; for 2h;
	With triethylamine
	With triethylamine In dichloromethane
	With triethylamine In dichloromethane at 0 - 20℃; for 18h; Inert atmosphere;
	With triethylamine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;

Reference： [1]Kortet, Sami; Claraz, Aurélie; Pihko, Petri M. [Organic Letters, 2020, vol. 22, # 8, p. 3010 - 3013]
[2]Martin, Stephen F.; Bur, Scott K. [Tetrahedron Letters, 1997, vol. 38, # 44, p. 7641 - 7644]
[3]Kemppainen, Eeva K.; Sahoo, Gokarneswar; Valkonen, Arto; Pihko, Petri M. [Organic Letters, 2012, vol. 14, # 4, p. 1086 - 1089]
[4]Manabe, Atsushi; Matsumoto, Ryotaro; Shinada, Tetsuro [Synlett, 2015, vol. 26, # 12, p. 1710 - 1714]
[5]Rosso, Giovanni B.; Pilli, Ronaldo A. [Tetrahedron Letters, 2006, vol. 47, # 2, p. 185 - 188]
[6]Martin, Stephen F.; Barr, Kenneth J.; Smith, Dudley W.; Bur, Scott K. [Journal of the American Chemical Society, 1999, vol. 121, # 30, p. 6990 - 6997]
[7]Boukouvalas, John; Loach, Richard P. [Journal of Organic Chemistry, 2008, vol. 73, # 20, p. 8109 - 8112]
[8]Funakoshi, Yuuta; Miura, Tomoya; Murakami, Masahiro [Organic Letters, 2016, vol. 18, # 24, p. 6284 - 6287]
[9]Neumeyer, Markus; Brückner, Reinhard [European Journal of Organic Chemistry, 2017, vol. 2017, # 17, p. 2512 - 2539]

23
[ 1009-61-6 ]
[ 80522-42-5 ]
1,4-bis-(1-triisopropylsilanyloxy-vinyl)-benzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1997,vol. 119,p. 10054 - 10063

24
[ 80522-42-5 ]
[ 13265-84-4 ]
[ 131216-78-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With 2,6-dimethylpyridine
78%	With 2,6-dimethylpyridine In dichloromethane at 20℃; for 1h;
	With 2,6-dimethylpyridine In dichloromethane at 0 - 20℃; for 2h;

Reference： [1]Abe, Hiroshi; Terauchi, Masaru; Matsuda, Akira; Shuto, Satoshi [Journal of Organic Chemistry, 2003, vol. 68, # 19, p. 7439 - 7447]
[2]Doetz, Karl Heinz; Otto, Frank; Nieger, Martin [Journal of Organometallic Chemistry, 2001, vol. 621, # 1-2, p. 77 - 88]
[3]Jäkel, Christoph; Dötz, Karl Heinz [Tetrahedron, 2000, vol. 56, # 15, p. 2167 - 2173]

25
[ 108-97-4 ]
[ 80522-42-5 ]
4-(triisopropyl-oxy)-pyranylium; trifluoro-methanesulfonate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2001,vol. 40,p. 568 - 570

26
[ 124-38-9 ]
[ 80522-42-5 ]
[ 1477-68-5 ]
[ 391609-22-6 ]

Reference： [1]Tetrahedron,2001,vol. 57,p. 319 - 329
[2]Journal of Organic Chemistry,2002,vol. 67,p. 3425 - 3436

27
[ 33689-29-1 ]
[ 80522-42-5 ]
[ 205756-59-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 619 - 622

28
[ 80522-42-5 ]
[ 709-50-2 ]
(2R,3R,4S,5R,6R)-2-Methoxy-3,4,5-tris-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	Stage #1: methyl beta-D-glucopyranoside With sodium hydride In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: triisopropylsilyl trifluoromethanesulfonate at 20℃; for 2.33333h;

Reference： [1]Abe, Hiroshi; Shuto, Satoshi; Tamura, Satoru; Matsuda, Akira [Tetrahedron Letters, 2001, vol. 42, # 35, p. 6159 - 6161]

29
[ 20662-89-9 ]
[ 80522-42-5 ]
4-phenyl-2-triisopropylsilanyl-oxazole [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 935 - 938

30
[ 2217-15-4 ]
[ 80522-42-5 ]
(2R,3R)-2-Hydroxy-3-triisopropylsilanyloxy-succinic acid diisopropyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With 2,5-dimethylpyridine In dichloromethane at 21℃;

Reference： [1]McNulty, James; Mao, Justin [Tetrahedron Letters, 2002, vol. 43, # 21, p. 3857 - 3861]

31
[ 4664-27-1 ]
[ 80522-42-5 ]
4-methyl-3-triisopropylsilanyloxymethyl-pyridine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 3009 - 3013

32
[ 10488-69-4 ]
[ 80522-42-5 ]
(S)-4-Chloro-3-triisopropylsilanyloxy-butyric acid ethyl ester [ No CAS ]

Reference： [1]Organic Letters,2002,vol. 4,p. 3231 - 3234

33
[ 75476-86-7 ]
[ 80522-42-5 ]
[ 552867-99-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 547 - 551

34
[ 1075-26-9 ]
[ 80522-42-5 ]
[ 345264-55-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3217 - 3220

35
[ 616-02-4 ]
[ 80522-42-5 ]
[ 203131-19-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: citraconic acid anhydride With sodium tetrahydroborate Stage #2: triisopropylsilyl trifluoromethanesulfonate With triethylamine In dichloromethane at 0 - 25℃; for 6h;
	Stage #1: citraconic acid anhydride With sodium tetrahydroborate Stage #2: triisopropylsilyl trifluoromethanesulfonate With triethylamine In dichloromethane at 0 - 25℃; for 6h;

Reference： [1]Vassilikogiannakis, Georgios; Margaros, Ioannis; Montagnon, Tamsyn [Organic Letters, 2004, vol. 6, # 12, p. 2039 - 2042]
[2]Vassilikogiannakis, Georgios; Margaros, Ioannis; Montagnon, Tamsyn; Stratakis, Manolis [Chemistry - A European Journal, 2005, vol. 11, # 20, p. 5899 - 5907]

36
[ 591-35-5 ]
[ 80522-42-5 ]
[ 216257-25-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 4h;	Preparation of 3,5-dichlorotriisopropylsilyloxybenzene (A1.1) To a solution of 200 g <strong>[591-35-5]3,5-dichlorophenol</strong> and 330 ml 2,6-lutidine in 3.0 1 dry CH2Cl2 400 g triisopropyl-silyltriflate was added at 0 C. within 1 h and the mixture was stirred for additional 3 hours at this temperature. After hydrolysis with 1.0 l water the organic layer was washed with saturated NaCl, dried over MgSO4 and evaporated to dryness (70 C./80 mbar). The residue was taken up in petroleum ether and filtrated through Silica to yield 360 g (92%) A1.1 as colorless oil. 1H-NMR (250 MHz, CDCl3) delta=1.03-1.15 (m, 18 H, CH3); 1.16-1.35 (m, 3 H CH); 6.73-6.80 (m, 2 H, CHarom.); 6.92-6.98 (m, 1 H, CHarom.) 13C-NMR (62.9 MHz, CDCl3) delta=12.7 (CH); 18.0 (CH3); 119.0, 121.6 (CHarom.); 135.2, 157.4 (Carom.)
92 - 100%	With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 2 - 4h;Product distribution / selectivity;	A Synthesis of Substituted 2,6-dichlorobenzaldehydes Example A1 [0082] 2,6-dichloro-4-hydroxybenzaldehyde (A1) [0083] Preparation of 3,5-dichlorotriisopropylsilyloxybenzene (A1.1) [0084] A solution of 4.08 g (25 mmol) <strong>[591-35-5]3,5-dichlorophenol</strong> and 6.70 g (62.5 mmol) 2,6-lutidine in 75 ml dry CH2Cl2 9.96 g (32.5 mmol) triisopropylsilyltriflate was mixed at 0[deg.] C. and stirred for 2 hours at this temperature. After hydrolysis with water (15 ml) the organic layer was washed with saturated NaCl, dried over MgSO4 and evaporated to dryness. Chromatography of the crude product on SiGel using iso-hexane as eluent returned A1.1 as a colorless oil in quantitative yield. [0085] <1>H-NMR (250 MHz, CDCl3) [delta]=1.03-1.15 (m, 18 H, CH3); 1.16-1.35 (m, 3 H CH); 6.73-6.80 (m, 2 H, CHarom.); 6.92-6.98 (m, 1 H, CHarom.) <13>C-NMR (62.9 MHz, CDCl3) [delta]=12.7 (CH); 18.0 (CH3); 119.0, 121.6 (CHarom.); 135.2, 157.4 (Carom.) [0086] Scale-Up [0087] A solution of 200 g <strong>[591-35-5]3,5-dichlorophenol</strong> and 330 ml 2,6-lutidine in 3.0 l dry CH2Cl2 400 g triisopropyl-silyltriflate was mixed at 0[deg.] C. within 1 h and the mixture was stirred for additional 3 hours at this temperature. After hydrolysis with 1.0 l water, the organic layer was washed with saturated NaCl, dried over MgSO4 and evaporated to dryness (70[deg.] C./80 mbar). The residue was taken up in petrol ether and filtrated through SiGel to yield 360 g (92%) A1.1 as colorless oil.
91%	With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 4h;	To a solution of <strong>[591-35-5]3,5-dichloro-phenol</strong> (5.9 g, 36 mmol) in methylene chloride (50 mL,) was added 2,6-lutidine (8.38 mL, 72.4 mmol) and triisopropylsilyl triflate (9.7 mL, 36 mmol) at 0 0C. The resulting mixture was stirred at 0 0C for 4 h. The reaction was quenched with 0.1 N HCl and diluted with ethyl acetate. The organic solution was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified with flash chromatography (5% ethyl acetate/hexanes) to give the desired product as a colorless oil (10.5 g, 91%). H NMR (400 MHz, CDCl3): delta 6.95 (t, J = 1.8 Hz, 1 H), 6.76 (d, J = 1.8 Hz, 2 H), 1.26 (m, 3 H), 1.09 (d, J = 7.0 Hz, 18 H).

With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 2h;

To a solution of <strong>[591-35-5]3,5-dichlorophenol</strong> (Intermediate 4) (70 g, 0.43 mol, 1.0 eq) in DCM (0.9 L) was added 2,6-lutidine (115.0 g, 1.07 mol, 2.5 eq). The solution was cooled to 0C. TIPS-OTf (171.1 g, 0.56 mol, 1.3 eq) was added dropwise. The mixture was stirred at 0C for 2h. The mixture was concentrated in vacuum. Petroleum ether (500 mL) was added, the resulting solution was washed with water (200mL*3), and brine (200 mL), then dried over Na2S04, and concentrated in vacuum to give the crude (3,5-dichlorophenoxy)-triisopropylsilane (Intermediate 5) (137 g, quantitative yield) as a yellow oil. This crude product was used for the next step without further purification.

Reference： [1]Synthesis,2004,p. 2062 - 2065
[2]Patent: US2005/85473,2005,A1 .Location in patent: Page/Page column 7
[3]Patent: US2003/199691,2003,A1 .Location in patent: Page/Page column 6
[4]Patent: WO2007/38215,2007,A1 .Location in patent: Page/Page column 106
[5]Patent: WO2019/160980,2019,A1 .Location in patent: Page/Page column 39; 40

37
[ 60211-57-6 ]
[ 80522-42-5 ]
[ 616195-94-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	With 2,6-dimethylpyridine; In dichloromethane; at 0℃; for 2h;	To a solution of <strong>[60211-57-6](3,5-dichlorophenyl)methanol</strong> (10.0 g, 56.5 mmol) in methylene chloride (100 mL) at 0 0C was added 2,6-lutidine (16.4 mL, 141 mmol) followed by triisopropylsilyl triflate (19.7 mL, 73.4 mmol), and was stirred at 0 0C for 2 hours. The reaction was diluted with water and the organic layer was separated, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by chromatography on silica gel, eluting with hexane to provide the desired product (14.8 g, 79%). LC/MS: 333 (M+H)+, 1H NMR (CDCl3) delta 7.23 (s, 3H), 4.78 (s, 2H), 1.18 (m, 3H), 1.03 (s, 18H).

Reference： [1]Synthesis,2004,p. 2062 - 2065
[2]Patent: WO2007/38215,2007,A1 .Location in patent: Page/Page column 99

38
[ 75-52-5 ]
[ 80522-42-5 ]
[ 147959-19-1 ]
4-(3-amino-2-triisopropylsilanyloxy-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 1423 - 1426
[2]Organic Letters,2005,vol. 7,p. 1423 - 1426

39
[ 75-52-5 ]
[ 80522-42-5 ]
[ 147959-19-1 ]
(4S)-2,2-dimethyl-4-[(2S)-2-triisopropylsilanyloxy-3-nitropropyl]oxazolidine-3-carboxylic acid tert-butyl ester [ No CAS ]
[ 850996-91-7 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 1423 - 1426
[2]Organic Letters,2005,vol. 7,p. 1423 - 1426

40
[ 5771-58-4 ]
[ 80522-42-5 ]
[ 163352-48-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With triethylamine In dichloromethane for 1.16667h;

Reference： [1]Yu, Jin-Quan; Wu, Hai-Chen; Corey [Organic Letters, 2005, vol. 7, # 7, p. 1415 - 1417]

41
[ 625-72-9 ]
[ 80522-42-5 ]
[ 126249-06-7 ]

Reference： [1]Journal of Organic Chemistry,2001,vol. 66,p. 1297 - 1309

42
[ 1192-62-7 ]
[ 80522-42-5 ]
[ 556025-76-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;	5 Example 5 : 2- [1-TRI-ISOPROPYLSILYLOXY-VINYL]-FURAN 2-Acetylfuran (SOg (0. 454MOL) is placed in a 2L IN round bottom flask and anhydrous CH2C12 (Aldrich Sure Seal, 0.70L) is added, followed by the addition of i-Pr2NEt (176g, 1. 36MOL, 3 eq., 237ML). The flask is equipped with a 125ML pressure equalized dropping funnel, and the mixture is placed under nitrogen and cooled in an ice-water bath. To the chilled ketone/amine mixture is added TIPSOTF (153.2g, 0. 5MOL, 1.1 eq. , 134. 3ML) over 1.5 hours. The mixture is allowed to warm to room temperature overnight. The reaction mixture is concentrated in vacuo on a rotary evaporator (T< 25°C) to give a yellow oil and a white solid. The flask contents are transferred to a 2L separatory funnel with ether (1.2L) resulting in the formation of additional white solid material (likely IPR2 (Et) NH+-OTf which might be removed by filtration but is not in this experiment) and the mixture is wash with saturated aq. NAHC03 (2X0. 70L). The organic phase is separated, dried over NA2S04, then is concentrated in vacuo to furnish the crude enol ether (118. 3g, 98%) as a yellow- orange oil. This crude material is not further purified, but is immediately carried to the next step. Physical Characteristics : 1H-NMR (400MHZ, CDC13) : 8 = 7.36, 6.49, 6.40, 4. 86, 4.37, 1.32, 1.14.
	With N-ethyl-N,N-diisopropylamine In dichloromethane cooling;

Reference： [1]Current Patent Assignee: PFIZER INC - WO2004/85414, 2004, A1 Location in patent: Page 16
[2]Tanis, Steven P.; Evans, Bruce R.; Nieman, James A.; Parker, Timothy T.; Taylor, Wendy D.; Heasley, Steven E.; Herrinton, Paul M.; Perrault, William R.; Hohler, Richard A.; Dolak, Lester A.; Hester, Matthew R.; Seest, Eric P. [Tetrahedron Asymmetry, 2006, vol. 17, # 14, p. 2154 - 2182]

43
[ 765-70-8 ]
[ 80522-42-5 ]
[ 1838-94-4 ]
3-methyl-2-(1-methyl-1-triisopropylsilanyloxymethyl-allyloxy)-cyclopent-2-enone [ No CAS ]
3-methyl-2-(1-methyl-1-triisopropylsilanyloxymethyl-allyloxy)-cyclopent-2-enone [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 4540 - 4541

44
[ 2700-30-3 ]
[ 80522-42-5 ]
diisopropyl-triisopropylsilanyloxymethylene-ammonium; trifluoro-methanesulfonate [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2006,p. 5076 - 5080

45
[ 80522-42-5 ]
[ 13500-53-3 ]
[ 944269-99-2 ]

Reference： [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 958 - 961

46
[ 80522-42-5 ]
[ 78162-58-0 ]
[ 936336-89-9 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1711 - 1715

47
[ 67853-03-6 ]
[ 80522-42-5 ]
[ 936336-90-2 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1711 - 1715

48
[ 80522-42-5 ]
[ 7473-36-1 ]
ethyl 2,3,4,6-tetrakis-O-(triisopropylsilyl)-1-thio-β-D-glucopyranoside [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 1573 - 1576

49
[ 627-32-7 ]
[ 80522-42-5 ]
[ 157035-91-1 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 9860 - 9861
[2]Journal of the American Chemical Society,2008,vol. 130,p. 12355 - 12369

50
[ 121-34-6 ]
[ 80522-42-5 ]
3-methoxy-4-triisopropylsilyloxybenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With triethylamine In DMF (N,N-dimethyl-formamide) at 0 - 20℃;	10.A A. 3-Methoxy-4-triisopropylsilyloxybenzoic Acid A 0° C. solution of vanillic acid (20 g; 119 mmol) in 550 mL of dry DMF and 33 mL of TEA was treated with TIPS-triflate (48 mL; 179 mmol) dropwise via a syringe. After 15 min, the reaction mixture was allowed to warm to ambient temperature. After stirring overnight, the reaction mixture was poured into 500 mL of saturated NaHCO3 (aq) and 300 mL of EtOAc. The aqueous layer was extracted with EtOAc (3×200 mL). The combined organic layers were washed with H2O (300 mL), dried over MgSO4, filtered and concentrated in vacuo. Purification by PrepLC (SiO2; 5% EtOAc in hexanes) afforded 22.5 g (69.3 mmol; 58%) of the title compound as fluffy white crystals. FDMS 324 (M+); Anal. Calcd. for C17H28O4Si: C, 62.92; H, 8.70. Found: C, 62.70; H, 8.81.

Reference： [1]Current Patent Assignee: ELI LILLY & CO - US6350774, 2002, B1 Location in patent: Page column 34

51
[ 80522-42-5 ]
[ 53342-27-1 ]
[ 556025-70-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃;	PREPARATION 19. 2-{1-[(Triisopropylsilyl)oxy]vinyl}pyrimidine. 2-Acetylpyrimidine (Khim. Geterotsikl. Soedin., (7), 958-62; 1981)(7.37g, 60.4mmol) and DIEA (23.4 g, 181.2 mmol) were dissolved in dry CH2Cl2 under N2 then cooled in an ice bath. TIPS-triflate (17.9 ml, 20.4 g, 66.4 mmol) was added over 2-3 min and stirred over night.The solvent was evaporated and the residue treated with ether (200 ml), filtered and washed with sat. sodium bicarbonate solution (2*50 ml).Evaporation gave a quantitative yield of the silyl ether as a red oil. Physical characteristics are as follows: HRMS (FAB) calcd for C15H26N2OSi+H 279.1892, found 279.1898. 1H NMR (300 MHz, CDCl3) delta 1.15 (18 H), 1.31 (3 H), 4.90 (1 H), 5.82 (1 H), 7.16 (1 H), 8.74 (2 H).

Reference： [1]Patent: US2004/138449,2004,A1 .Location in patent: Page 27

52
[ 20274-69-5 ]
[ 80522-42-5 ]
[ 1366097-28-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-dimethylpyridine; In dichloromethane; at 20℃;	To a solution [OF 4-FLUORO-3-NITROBENZYL] alcohol (1.023 g, 5.98 mmol) in dichloromethane (50 mL) at room temperature was added 2,6-lutidine (0. [836] mL, 7.17 mmol) followed by triisopropylsilyl [TRIFLUOROMETHANESULFONATE] (1.77 mL, 6.57 mmol). After stirring overnight, the solution was washed with water, the aqueous extracted with dichloromethane, the organics combined, dried over anhydrous magnesium sulfate, and concentrated to afford the [TRI-ISOPROPYLSILYL] protected as a brown oil used as is in the next reaction.
7 mg	With 2,6-dimethylpyridine; In dichloromethane; at 20℃;	To a stirred solution of <strong>[20274-69-5](4-fluoro-3-nitrophenyl)methanol</strong> (5.0 g, 29.217 mmol) in dichloromethane (100 ml) was added 2,6-lutidine (3.57 g, 35.061 mmol) followed by triisopropylsilyltrifluoromethanesulfonate (8.669 ml, 32.317 mmol) and stirred at room temperature overnight. The reaction mixture was washed with water (150 ml) and the aqueous layer was extracted with dichloromethane (2 x 150 ml). The combined organic layer was washed with water (200 ml), brine (200 ml), dried over Na2SO4 and concentrated under reduced pressure to give 7.0 mg of ((4-fluoro-3-nitrobenzyl)oxy)triisopropylsilane as a pale yellow oil. 1H NMR (300 MHz, DMSO-d6): delta 0.92-1.07 (m, 18H), 1.10-1.22 (m, 3H), 4.88 (s, 2H), 7.54-7.62 (m, IH), 7.75 (br s, IH), 8.12 (d, / = 7.5 Hz, 1H); ESI-MS (m z): 327 (M+H)+.

Reference： [1]Patent: WO2004/14905,2004,A1 .Location in patent: Page 164
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 1588 - 1591
[3]Patent: WO2013/24427,2013,A1 .Location in patent: Page/Page column 52

53
[ 80522-42-5 ]
[ 1122-63-0 ]
[ 672950-11-7 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃; for 6.06667h;	Triisopropylsilyl triflate (26.4 g) is added over 4 min. to an ice cooled solution [OF 3-] acetylpyridazine (9.57 g) and diisopropylethylamine [(30.] 4 g) in dry [CH2C12] [(100 ML)] under nitrogen. After 4 h, the solvent is evaporated and the residue extracted with diethyl ether (150 mL). The organic layer is washed with saturated aq. sodium bicarbonate solution (2 [X] [60] mL) followed by brine (60 [ML),] dried [(MGSO4),] filtered and evaporated.. The crude product is purified by column chromatography [(HEXANES/ETOAC,] 9/1) to afford 13.4 g of the title compound as a yellow oil. Physical [CHARACTERISTICS. 1H NMR (400 MHz, CDCl3) delta 9.10, 7.85, 7.52, 5.98, 4.74, 1.35, 1.16 ; HRMS (ESI) m/z 279.1879

Reference： [1]Patent: WO2004/22567,2004,A1 .Location in patent: Page 52

54
[ 32161-06-1 ]
[ 80522-42-5 ]
1-acetyl-4-piperidinonetriisopropylsilyl enolate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With 2,6-dimethylpyridine; In dichloromethane; at 20℃; for 2h;	The title compound described in Example 5 can also be produced by the method described below. (Step 1) To a solution of 1.4 g (0.01 mole) of <strong>[32161-06-1]1-acetyl-4-piperidinone</strong> and 2.2 g of 2, 6-lutidine in 10 ml of dichloromethane was added 5.3 ml of triisopropylsilyl triflate under ice-cooling.. After stirring at room temperature for 2 hours, the mixture was washed with water and then with diluted hydrochloric acid.. After drying over magnesium sulfate, the solvent was distilled off to obtain <strong>[32161-06-1]1-acetyl-4-piperidinone</strong>triisopropylsilyl enolate quantitatively.

Reference： [1]Patent: EP1460062,2004,A1 .Location in patent: Page 81

55
[ 108-48-5 ]
[ 75476-86-7 ]
[ 80522-42-5 ]
[ 552867-99-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In dichloromethane;	Example 156, Part A 6-Bromo-2,3-dihydro-1-[[tris(1-methylethyl)silyl]oxy]-1H-indene To <strong>[75476-86-7]6-Bromo-2,3-dihydro-1H-inden-1-ol</strong> (300 mg, 1.41 mmol) in CH2Cl2 (4 mL) was added 2,6-lutidine (151 muL, 1.4 mmol) followed by triisopropylsilyltriflate (378 muL, 1.41 mmol) at room temperature. The reaction was stirred for 30 min then added to 1N HCl and extracted. The organic layer was washed with saturated sodium bicarbonate then brine and dried over MgSO4. The solvent was removed in vacuo and the crude material purified by column chromatography.

Reference： [1]Patent: US2002/40022,2002,A1

56
aqueous Na₂ CO₃ [ No CAS ]
[ 73-31-4 ]
[ 80522-42-5 ]
[ 256345-35-4 ]

Yield	Reaction Conditions	Operation in experiment
	With KH; In tetrahydrofuran; ethyl acetate; mineral oil;	EXAMPLE 1 Synthesis of 1-Triisopropylsilylmelatonin A portionwise addition of 2.00 g (17.5 mmol) of a 35 wt. % dispersion of KH in mineral oil was made to a solution of 2.00 g (8.62 mmol) of melatonin in 30 mL of tetrahydrofuran. The mixture was stirred until there was no further evidence of reaction. The resulting slurry was treated with 2.70 ml (5.30 g, 17.2 mmol)of triisopropylsilyl triflate. The reaction was stirred overnight. The reaction was worked up by adding it to dilute aqueous Na2 CO3 and extracting the product into CH2 Cl2. The extract was washed with NaCl solution, then dried over Na2 SO4. The CH2 Cl2 was evaporated leaving a viscous oil. The oil was chromatographed over 400 g of silica gel using ethyl acetate. The purified product from the column weighed 3.02 g (90% yield). It was followed by 0.058 g of starting material. Upon standing, the product crystallized. m.p.: 127-128.5 C.; MS (esi+), m/e=389.4 (M+1); Analysis for C22 H36 N2 O2 Si: Calculated: C, 67.99; H, 9.34; N, 7.21; Found: C, 68.76; H, 9.66; N, 7.50.

Reference： [1]Patent: US6022980,2000,A

57
[ 7651-83-4 ]
[ 80522-42-5 ]
[ 887343-40-0 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In N,N-dimethyl-formamide;	Commercially available 7-hydroxyisoquinolme (1 g, 6.9 mmol) was combined with triisopropylsilyl trifluoromethanesulfonate (3.7 mL, 13.8 mmol) in (1 : 1) pyridine-dimethylformarmde (10 mL) Upon reaction completion, the mixture was partitioned between saturated aqueous copper sulfate and ethyl acetate, the organic phase separated, dried, and concentrated in vacuo. The crude silyl ether was purified by flash column chromatography (Biotage, SiO2, 30% acetone-hexane) to provide the pure product (2.4 g) which was oxidized with meta-chloroperbenzoic acid m a similar manner as described in the examples above. This TIPS-ether isoqumolme N-oxide (1.95 g, 6.14 mmol) was combined with toluenesulfonyl chloride (1.5 g, 7.9 mmol), triethylamine (1.7 mL, 12.3 mmol), and maintained overnight in methanol (30 mL). The crude methoxyisoquinolme product was purified by flash column chromatography (Biotage, SiO2), and then desilylated with HF-pyridine m tetrahydrofuran. Triflation of the phenolic moiety and Heck coupling was performed in a similar manner as described in EXAMPLE 54 above and illustrated in Scheme 9. The resultant methoxyisoquinolme acrylamide benzyl ester intermediate was hydrogenated with Pearlman's catalyst in a similar manner as described in the examples above to provide the desired product: 1H NMR (CD3OD 500 MHz) delta 8.6 (d, 1H), 8.1 (s, 1H), 8.0 (d, 1H), 7.9 (d, 1H), 7.8 (d, 1H), 7.7 (d, 1H), 7.5 (m, 1H), 7.3 (d, 1H), 7.1 (t, 1H), 4.1 (s, 3H), 3.2 (t, 2H), 2.8 (t, 2H), LCMS m/z 351 (M++1)

Reference： [1]Patent: WO2006/52555,2006,A2 .Location in patent: Page/Page column 68

58
[ 80522-42-5 ]
[ 651744-48-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-chloro-7-azaindole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: triisopropylsilyl trifluoromethanesulfonate In tetrahydrofuran; hexane at -78 - 20℃;	1 To a solution of 4-chloro-lH-pyrrolo[2,3-]pyridine (3.21 g, 21 mmol) inTΗF (60 mL), cooled at -78 0C, is added slowly R-BuLi (1.6 M in hexane, 13.8 mL, 22 EPO mmol). After stirring for 30 minutes, the TIPSOTf (5.77 mL, 21.4 mmol) is added. The mixture is allowed to rise to room temperature and quenched with water. The mixture is partitioned between hexanes (200 mL) and brine. The organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated. The residue is purified by column chromatography (silica gel, eluting with hexanes) to afford the title compound: 1H NMR 600 MHz (Acetone-4) δ 8.19 (d, IH, J= 5.4 Hz), 7.57 (d, IH, J= 3.0 Hz), 7.18 (d, IH, J= 5.4 Hz), 6.69 (d, IH, J= 3.0 Hz), 1.92 (sept, 3H, J= 7.2 Hz ), 1.12 (d, 18H, J= 7.2 Hz); MS m/z 309.2 (M + 1).

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH; IRM LLC - WO2007/22268, 2007, A2 Location in patent: Page/Page column 23-24

59
[ 2013-12-9 ]
[ 80522-42-5 ]
[ 1006035-50-2 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 333 - 336
[2]Heterocycles,2010,vol. 80,p. 409 - 426

60
[ 80522-42-5 ]
[ 87745-27-5 ]
[ 355121-63-0 ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 4149 - 4157

61
[ 80522-42-5 ]
[ 87745-27-5 ]
[ 917486-58-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 4149 - 4157

62
[ 80522-42-5 ]
[ 55052-28-3 ]
[ 651744-48-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-chloro-7-azaindole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: triisopropylsilyl trifluoromethanesulfonate In tetrahydrofuran; hexane at -78 - 20℃;	1.1 1. 4-Chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine To a solution of 4-chloro-1H-pyrrolo[2,3-b]pyridine (3.21 g, 21 mmol) in THF (60 mL), cooled at -78° C., is added slowly n-BuLi (1.6 M in hexane, 13.8 mL, 22 mmol). After stirring for 30 min, the TIPSOTf (5.77 mL, 21.4 mmol) is added. The mixture is allowed to rise to room temperature and quenched with water. The mixture is partitioned between hexanes (200 mL) and brine. The organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated. The residue is purified by column chromatography (silica gel, eluding with hexanes) to afford the title compound. 1H NMR 600 MHz (Acetone-d6) δ 8.19 (d, 1H, J=5.4 Hz), 7.57 (d, 1H, J=3.0 Hz), 7.18 (d, 1H, J=5.4 Hz), 6.69 (d, 1H, J=3.0 Hz), 1.92 (sept, 3H, J=7.2 Hz), 1.12 (d, 18H, J=7.2 Hz); MS m/z 309.2 (M+1).
	Stage #1: 4-chloro-7-azaindole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: triisopropylsilyl trifluoromethanesulfonate In tetrahydrofuran; hexane at -78 - 20℃;	2 To a solution of 4-chloro-lH-pyrrolo[2,3-£]pyridine (3.21 g, 21 mmol) in TηF (60 mL), cooled at -78 0C, is slowly added n-BuLi (1.6 M in hexane, 13.8 mL, 22 mmol). After stirring for 30 minutes, TIPSOTf (5.77 mL, 21.4 mmol) is added. The mixture is allowed to rise to room temperature and quenched with water. The mixture is partitioned between hexanes (200 mL) and brine. The organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated. The residue is purified by column chromatography (silica gel, eluting with hexanes) to afford the title compound. 1H NMR 600 MHz (acetone-J6) δ 8.19 (d, IH, J = 5.4 Hz), 7.57 (J, IH, J = 3.0 Hz), 7.18 (J, IH, J = 5.4 Hz), 6.69 (d, IH, J = 3.0 Hz), 1.92 (sept, 3H, J = 7.2 Hz ), 1.12 (J, 18H, J = 7.2 Hz); MS m/z 309.2 (M + 1).
	Stage #1: 4-chloro-7-azaindole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: triisopropylsilyl trifluoromethanesulfonate In tetrahydrofuran; hexanes at -78 - 20℃;	1.1 Example 1N-ethyl-S-rg-ethyl-δ-oxo-S^^^-tetrahvdro-S^J^-tetraaza-cyclorjentaralnaphthalen-y-yl")-5-methoxv-benzamide EPO [0078] 1. 4-Chloro-l-triisopropylsilanyl-lH-pyrrolo[2,3-]pyridine; [0079] To a solution of 4-chloro- lH-pyrrolo [2,3-]pyridine (3.21 g, 21 mmol) inTΗF (60 mL), cooled at -78 0C, is added slowly n-BuLi (1.6 M in hexane, 13.8 mL, 22 mmol). After stirring for 30 minutes, the TIPSOTf (5.77 mL, 21.4 mmol) is added. The mixture is allowed to rise to room temperature and quenched with water. The mixture is partitioned between hexanes (200 mL) and brine. The organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated. The residue is purified by column chromatography (silica gel, eluting with hexanes) to afford the title compound: 1H NMR 600 MHz (acetone-^) δ 8.19 (d, IH, J= 5.4 Hz), 7.57 (d, IH, J= 3.0 Hz), 7.18 (d, IH, J = 5.4 Hz), 6.69 (d, IH, J= 3.0 Hz), 1.92 (sept, 3H, J= 7.2 Hz ), 1.12 (d, 18H, J= 7.2 Hz); MS m/z 309.2 (M + 1).

Reference： [1]Current Patent Assignee: IRM LLC - US2010/48552, 2010, A1 Location in patent: Page/Page column 10
[2]Current Patent Assignee: IRM LLC - WO2008/144253, 2008, A1 Location in patent: Page/Page column 31
[3]Current Patent Assignee: IRM LLC - WO2006/124731, 2006, A2 Location in patent: Page/Page column 24-25

63
[ 80522-42-5 ]
[ 70782-12-6 ]
[ 680569-99-7 ]

Yield	Reaction Conditions	Operation in experiment
		Step2 triphenylphosphine (1.15 g, 4.39 mmol) and N-bromosuccinimide (0.79 g, 4.39 mmol) were added to a 0 C. solution of <strong>[70782-12-6]N-Cbz-diethanolamine</strong> (1 g, 4.18 mmol) in 40 ml of methylene chloride.The reaction was stirred at room temperature for 4 hours and then cooled to 0 C. 2,6-Lutidine (0.97 ml, 8.36 mmol) was added, followed by the dropwise addition of triisopropylsilyl triflate (1.35 ml, 5 mmol).The reaction was stirred at room temperature for 12 h, diluted with water, and concentrated under vacuum and the residue was extracted with ethyl acetate (2*50 ml).The organic layer was washed with 0.5 M HCl, saturated sodium bicarbonate, brine and dried over sodium sulfate.Evaporation of the solvent followed by chromatography (SiO2 Biotage 40 M, 3%-5% ethyl acetate/hexanes) gave (2-bromo-ethyl)-(2-triisopropylsilanyloxy-ethyl)-carbamic acid benzyl ester (400 mg) as a clear oil.

Reference： [1]Patent: US2004/77646,2004,A1 .Location in patent: Page 128

64
[ 80522-42-5 ]
[ 1173824-58-2 ]
[ 1151529-00-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With 2,6-dimethylpyridine In dichloromethane at 0℃; for 1h;	701 Example 701:Compound 605B (8.0 g, 21.2 mmol) was dissolved in anhydrous DCM (100 mL). To the solution at 0 °C was added 2,6-ludine (2.7 mL, 23.3 mmol), followed by dropwise addition of triisopropylsilyl trifluoromethanesulfonate (6.0 mL, 23.3 mmol). The solution was stirred at 0 °C for 1 h. The solvent was removed in vacuo and the residue was purified using silica gel chromatography with a gradient of 0-20% EtOAc in hexane to afford 701 (9.6 g, 85%). 1H NMR (CDCI3) δ 8.07 (d, J= 8.0 Hz, 2H), 7.98 (d, J = 8.0 Hz, 2H), 7.60 (dd, J = 7.5, 7.5 Hz, 1 H), 7.51 (dd, J * 7.5, 7.5 Hz, 1 H), 7.46 (dd, J = 8.0, 7.5 Hz, 2H), 7.33 (dd, J= 8.0, 7.5 Hz, 2H), 5.79 (m, 1H), 5.33 (d, J = 6.9 Hz, 1 H), 4.68 (m, 1 H), 4.51 (2H, m), 1.07 (m, 21 H).

Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2009/61781, 2009, A1 Location in patent: Page/Page column 105

65
[ 58556-75-5 ]
[ 80522-42-5 ]
[ 1165944-09-1 ]

Yield	Reaction Conditions	Operation in experiment
61%		Example 1 - Synthesis of (7-Bromonaphthalen-2-yl)triisopropylsilane; <n="15"/>To a solution of <strong>[58556-75-5]2,7-dibromonaphthalene</strong> 8 (10.4 g, 0.036 mol) in THF (300 ml) at -780C was added 23 ml of 1.7 M t-BuLi solution in pentane. The mixture was stirred at -780C for 1 hour and triisopropylsilyl(TIPS)-triflate (9.17 ml, 0.036 mol) was added while the reaction mixture temperature was maintained below -6O0C. The reaction mixture was stirred overnight and allowed to reach the room temperature. The workup involved addition of aqueous sat. NH4Cl (100 ml) and extraction of the product with methyl £-butyl ether (MTBE). After drying over anhydrous Na2SO4 and filtration, the MTBE solution was concentrated under reduced pressure. The product was purified on a 120 g SiO2 pre-packed column, using cyclohexane for elution. The product- containing fractions were concentrated to yield 8 g (61%) of 2-bromo-7- triisopropylsilyl naphthalene 9.

Reference： [1]Patent: WO2009/80716,2009,A1 .Location in patent: Page/Page column 13-14

66
[ 2896-67-5 ]
[ 80522-42-5 ]
triisopropyl-(2-methoxy-4-methylphenoxy)silane [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 13928 - 13929

67
[ 949480-57-3 ]
[ 80522-42-5 ]
[ 1210360-52-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine In dichloromethane at 20℃; for 2h;

Reference： [1]Jiang, Hao; Paixao, Marcio W.; Monge, David; Jorgensen, Karl Anker [Journal of the American Chemical Society, 2010, vol. 132, # 8, p. 2775 - 2783]

68
[ 118599-27-2 ]
[ 80522-42-5 ]
[ 1222558-44-2 ]

Yield	Reaction Conditions	Operation in experiment
35%		A 2 L dry round bottom flask was charged with N-benzyl-3,6- dibromocarbazole 3 (49 g, 0.118 mol) and 1 L of dry THF was added. The mixture was stirred until N-benzyl-3,6-dibromocarbazole 3 was dissolved. The mixture was then cooled to -780C and 2.5 M n-BuLi in hexanes (104 ml, 0.26 mol) was added dropwise. The mixture was stirred at -780C for 15 min and triisopropylsilyl-trifluoromethyl sulfonate (66 ml, 0.26 mol) was added. The mixture was left to warm up to room temperature overnight. The mixture was then quenched with sat. NH4CI, extracted with methyl-f- butyl ether, dried over Na2SO4, filtered, concentrated, and purified over a 330 g Sitheta2 column to yield 9-benzyl-3,6-bis-triisopropylsilanyl-9/-/- carbazole 4 23.0 g (35%) as a transparent oil.

Reference： [1]Patent: WO2010/43693,2010,A1 .Location in patent: Page/Page column 15

69
3-bromo-9-benzyl-9H-carbazole [ No CAS ]
[ 80522-42-5 ]
[ 19402-87-0 ]
[ 1233659-43-2 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of 3.854 g (11.46 mmol) of 9-N-benzyl-3-bromocarbazole 5 in 70 ml of anhydrous THF was cooled to -780C, and 5.0 ml of n-BuLi (2.5 M/hexane, 12.5 mmol, 1.1 eg.) was slowly added using a syringe at a suitable rate for maintaining a temperature below -740C. The resulting yellow solution was stirred at -780C for 40 minutes, and then neat triisopropylsilyl triflate (TIPS-triflate) was added dropwise to the reaction mixture using a syringe. The reaction mixture was stirred for 30 minutes and was then slowly allowed to warm up to room temperature for a period of two hours. The reaction mixture was quenched with ice water, extracted with ethyl acetate (3x50 ml), and the organic phase was dried over Na2SO4. After concentration on a rotary evaporator, a colorless oil was purified on CombiFlash (120 g column, hexane) to afford 2.55 g of clear oil. Although this material produces one spot on TLC (Rf = 0.67 in EtOAc/hexane = 1 :9), a second spot related to the reduced material 7 can be seen in hexane (Rf = 0.27 for 6 and Rf = 0.19 for 7). The HPLC results indicated that the oil contained about 60% of the product 9-N-benzyl-3- triisopropylsilyl-carbazole 6. This material was used for the following de- protection step. Only a trace amount (0.115 g) of the pure 9-N-benzyl-3- triisopropylsilyl-carbazole 6 was isolated to confirm the product's structure.

Reference： [1]Patent: WO2010/43693,2010,A1 .Location in patent: Page/Page column 20

70
[ 1192217-75-6 ]
[ 80522-42-5 ]
[ 1229516-62-4 ]
[ 1229516-63-5 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-(benzenesulfonyl)-3-bromo-1H-pyrrole With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: triisopropylsilyl trifluoromethanesulfonate In tetrahydrofuran; hexane at -78 - 0℃; regioselective reaction;

Reference： [1]Fukuda, Tsutomu; Ohta, Takeshi; Sudo, Ei-Ichi; Iwao, Masatomo [Organic Letters, 2010, vol. 12, # 12, p. 2734 - 2737]

71
[ 80522-42-5 ]
[ 155380-11-3 ]
[ 1253955-08-6 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20℃;	Methyl 2-(4-((triisopropylsilyloxy)methyl) phenyl)acetate (E133) was prepared from E132 according to the below: E132E133To <strong>[155380-11-3]methyl 2-(4-(hydroxymethyl)phenyl)acetate</strong> (E132) in CH2CI2 at O0C was added 2,6- lutidine and TIPS-OTf. The ice bath was removed and the solution was allowed to warm to room temperature and stir. After 4 h the solution was poured into NH4CI(sat) and CH2CI2 and the organic layer was further extracted with NH4CI(sat). The organics were dried (MgSO4) filtered and evaporated. Column chromatography (SiO2, 0-15% EtOAc/Hexanes) gave pure methyl 2-(4-((triisopropylsilyloxy)methyl)phenyl)acetate (E133).
	With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20℃; for 2.0h;	To a zero degree solution of <strong>[155380-11-3]methyl 2-(4-(hydroxymethyl)phenyl)acetate</strong> (11b) (5674 mg, 31.49 mmol) in CH2Cl2 (50 mL), 2,6-lutidine (5.47 mL, 47.23 mmol) and TIPS-OTf (14.48 g, 47.23 mmol) were added. The ice bath was removed and the solution was allowed to warm to room temperature and stirred. After 2 hours, the reaction was quenched by the addition of NH4Cl(aq) (50 mL). The reaction was diluted with CH2Cl2 (100 mL) and washed with H2O (2 x 50 mL) and brine (50 mL). The organic layer was dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (0 to 5 percent EtOAc/hexanes) to afforded methyl 2-(4-(((triisopropylsilyl)oxy)methyl)phenyl)acetate (11c). 1H-NMR (500 MHz, CDCl3): δ 7.31 (d, J=8.0 Hz, 2H), 7.24 (d, J=8.0 Hz, 2H), 4.82 (s, 2H), 3.69 (s, 3H), 3.62 (s, 2H), 1.21-1.15 (m, 3H), 1.10-1.06 (m, 18H)

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 2475 - 2480
[2]Patent: WO2010/127329,2010,A1 .Location in patent: Page/Page column 54
[3]Patent: EP3845276,2021,A1 .Location in patent: Paragraph 0061; 0096; 0098

72
[ 14199-15-6 ]
[ 80522-42-5 ]
[ 243641-04-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With 2,6-dimethylpyridine In dichloromethane at 0 - 20℃;	2 methyl 2-(4-(triisopropylsilyloxy)phenyl)acetate (E2) was synthesized from E1 according to the below:To methyl 2-(4-hydroxyphenyl)acetate (E1 ) in CH2CI2 at 00C was added 2,6-lutidine and TIPS-OTf. The ice bath was removed and the solution was allowed to warm to room temperature and stirred. After 4 h the solution was poured into NH4CI(Sat) and CH2CI2 and the organic layer was further extracted with NH4CI(Sat). The organics were dried (Na2SO4) filtered and evaporated. Column chromatography (0-15% EtOAc/Hexanes) gave pure methyl-2-(4-(triisopropylsilyloxy)phenyl)acetate (E2).
91%	With 2,6-dimethylpyridine In dichloromethane
91%	With 2,6-dimethylpyridine In dichloromethane

Reference： [1]Current Patent Assignee: AERIE PHARMACEUTICALS INC - WO2010/127329, 2010, A1 Location in patent: Page/Page column 44
[2]Sturdivant, Jill M.; Royalty, Susan M.; Lin, Cheng-Wen; Moore, Lori A.; Yingling, Jeffrey D.; Laethem, Carmen L.; Sherman, Bryan; Heintzelman, Geoffrey R.; Kopczynski, Casey C.; Delong, Mitchell A. [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 10, p. 2475 - 2480]
[3]Current Patent Assignee: AERIE PHARMACEUTICALS INC - WO2018/34702, 2018, A1 Location in patent: Paragraph 0070; 00140

73
[ 3967-53-1 ]
[ 80522-42-5 ]
[ 1253955-62-2 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-dimethylpyridine In dichloromethane at 0 - 20℃; for 2h;	399 Methyl 2-phenyl-3-(triisopropylsilyloxy)propanoate (E399) was prepared from E398 according to the below:To methyl 3-hydroxy-2-phenylpropanolate in CH2CI2 was at O0C was added 2,6-lutidine and TIPS-OTf, and this solution was stirred for 2 h at room temperature. The mixture was poured into NH4CI(Sat) and extracted with CH2CI2. The organics were dried (Na2SO4), filtered, and evaporated. Column chromatography 0-10% EtOAc/Hex gave pure methyl 2-phenyl-3- (triisopropylsilyloxy)propanoate (E399).

Reference： [1]Current Patent Assignee: AERIE PHARMACEUTICALS INC - WO2010/127329, 2010, A1 Location in patent: Page/Page column 101

74
[ 27727-37-3 ]
[ 80522-42-5 ]
[ 1253955-44-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-dimethylpyridine In dichloromethane at 0℃; for 2.5h;	302 Benzyl 2-(4-(triisopropylsiloxy)phenyl)acetate (E302) was prepared from E301 according to the below:To benzyl 2-(4-hydroxyphenyl)acetate (E301 ) in CH2CI2 at O0C was added 2,6-lutidine and TIPS-OTf and the solution stirred for 2.5 h at O0C. The mixture was poured into NH4CI(Sat) and extracted with CH2CI2. The combined organics were dried (Na2SO4), filtered, and evaporated. Column chromatography (SiO2, 0-15% EtOAc/Hex) gave pure benzyl 2-(4- (triisopropylsiloxy)phenyl)acetate (E302).
	With 2,6-dimethylpyridine In dichloromethane at 0℃; for 2.5h;	Preparation of benzyl 2-(4-(triisopropylsiloxy)phenyl)acetate (E76). To benzyl 2-(4-hydroxyphenyl)acetate (E75) in CH2CI2 at 0 °C was added 2,6- lutidine and TIPS-OTf and the solution stirred for 2.5 hours at 0 °C. The mixture was poured into NH4CI (Sat) and extracted with CH2CI2. The combined organics were dried (Na2S04), filtered and evaporated. Column chromatography (S1O2, 0-15% EtOAc/Hex) gave pure benzyl 2-(4-(triisopropylsilyloxy) phenyl)acetate (E76).

Reference： [1]Current Patent Assignee: AERIE PHARMACEUTICALS INC - WO2010/127329, 2010, A1 Location in patent: Page/Page column 86
[2]Current Patent Assignee: AERIE PHARMACEUTICALS INC - WO2019/178324, 2019, A1 Location in patent: Paragraph 00239-00240

75
[ 80522-42-5 ]
[ 7306-68-5 ]
[ 1262785-82-9 ]

Yield	Reaction Conditions	Operation in experiment
80%		In a dry flask, a solution of lithium amide (LiTMP or LDA) was prepared in situ from n-butyllithium (n-BuLi, 1.6 M in hexane) and the corresponding amine (diisopropylamine for LDA and tetramethylpiperidine for LiTMP) in freshly distilled THF (Na/benzophenone) and stirred for 30 min at -78 C under positive pressure of argon. A solution 6-Chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine (1) in freshly distilled THF was then added dropwise and stirred over 1 h with LDA and 2 h with LiTMP at -78 C. A solution of the electrophile in THF was then added dropwise (unless mentioned otherwise) and the resulting mixture was stirred over 1 hour while maintaining the temperature at -78 C, before it was warmed to room temperature. Water was added and the mixture was extracted twice with AcOEt. The organic layers were combined, dried over MgSO4 and evaporated under vacuum. The crude material was purified by flash chromatography on silica gel eluting with a gradient of DCM/EtOH (0-1 %).

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 305 - 307

76
[ 80522-42-5 ]
[ 142-30-3 ]
[ 1303459-35-9 ]

Yield	Reaction Conditions	Operation in experiment
72%	With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20℃;	Compound 1e: To a solution of <strong>[142-30-3]2,5-dimethyl-3-hexyne-2,5-diol</strong> (427 mg, 3.00 mmol) and 2,6-lutidine (0.35 mL, 3.0 mmol) in CH2Cl2 (10 mL) was added triisopropylsilyl triflate (0.80 mL, 3.0 mmol) at 0 C. The mixture was slowly warmed to room temperature and stirred for 15 h. Aqueous NaHCO3 was added to the mixture and it was extracted with CH2Cl2. The combined organic extracts were washed with water, dried over MgSO4, filtered, and concentrated on a rotary evaporator. The residue was subjected to flash column chromatography on silica gel with EtOAc/hexane (1/5) to give 1e (643 mg, 2.15 mmol, 72% yield).

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 2185 - 2187

77
[ 80522-42-5 ]
[ 73724-48-8 ]
[ 1353655-04-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine; In dichloromethane; at 0 - 20℃; for 1h;Inert atmosphere;	At r.t. a solution of FmocONSu (3.37 g, 10.0 mmol) in 25 mL of Dioxane12 is added over 1h to a solution of L-threonine (1.19 g, 10.0 mmol) and Na2CO3 (1.06 g, 10.0 mmol) in 10 mL Dioxane and 25 mL water. The resulting suspension is stirred overnight and becomes clear. The solvent is evaporated in vacuo and the product is precipitated with 1M HClaq. at pH 4, filtered, washed with water and dissolved in EtOAc. The organic phase is dried (Na2SO4) and evaporated to yield the product quantitatively as a white solid which does not need any further purification. Under argon atmosphere Fmoc-threonine (2.67 g, 7.80 mmol) is dissolved in 32 mL dry MeOH. Then Cs2CO3 (1.40 g, 4.30 mmol) is added.11 After 15 min the solvent is evaporated and the resulting solid is three times suspended in CH2Cl2 and evaporated to remove all the MeOH. The Cs-salt is then suspended in 36 mL of dry DMF under argon atmosphere and stirred with benzylbromide (1.02 mL, 1.47 g, 8.60 mmol) over night at r.t. After evaporation of the solvent in vacuo, the residue is partitioned between water and CH2Cl2. The water phase is subsequently extracted two times with EtOAc. The combined organic phases are dried (Na2SO4) and evaporated. The crude product is purified either by recrystallisation from EtOAc or by silica column chromatography (cyclohexane/EtOAc 4 : 1) to get Fmoc-threoninebenzylester (3.07 g, 7.10 mmol, 91%, Rf = 0.17 (cyclohexane/EtOAc 3 : 1)) as a white solid. The Fmoc-threoninebenzylester (2.16 g, 5.00 mmol) is dissolved in 48 mL dry CH2Cl2 under argon atmosphere. The solution is cooled to 0C and NEt3 (770 muL, 560 mg, 5.50 mmol) and Triisopropylsilyltriflat (1.42 mL, 1.61 g, 5.25 mmol) is added subsequently.12 The mixture is allowed to warm to r.t. and is stirred 1h. Then 30 mL of dilute K2CO3- solution is added. The phases are separated and the water phase is extracted two times with CH2Cl2. The combined organic phases are dried (Na2SO4) and evaporated. The crude product is purified by silica column chromatography (cyclohexane/EtOAc 10 : 1) to get Fmoc(OTIPS)benzylester (2.47 g, 4.20 mmol, 84%, Rf = 0.61 (cyclohexane/EtOAc 3 : 1)) as a colourless oil. Fmoc(OTIPS)benzylester (0.87 g, 1.48 mmol) is dissolved in 7.4 mL dry CH2Cl2 under argon atmosphere. The solution is cooled to 0C and 7.4 mL of 40% (v/v) Piperidine solution in dry CH2Cl2 are added dropwise.13 After 15 min of stirring at 0C, the mixture is concentrated in vacuo at 25C to an oil and put immediately onto the silica column (cyclohexane/EtOAc 5 : 1 + 0.5% NEt3, elution of product with 1 : 1 + 0.5% NEt3). Yield of the title compound 17d is 0.44 g (1.20 mmol, 81%) as a colourless oil.

Reference： [1]Tetrahedron,2012,vol. 68,p. 697 - 704

78
[ 3262-72-4 ]
[ 80522-42-5 ]
[ 421556-56-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: (S)-N-(tert-butoxycarbonyl)serine; triisopropylsilyl trifluoromethanesulfonate With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine at 0 - 20℃; Stage #2: With potassium carbonate In methanol; water for 1h; Stage #3: With hydrogenchloride In methanol; water	(S)-2-((tert-butoxycarbonyl)amino)-3-((triisopropylsilyl)oxy)propanoic acid, 24 To a stirring solution of (L)-Boc-Ser-OH 23 (410 mg, 2 mmol) and TEA (0.56 mL, 4 mmol) in 4 mL of dichloromethane, was added triisopropylsilyl trifluoromethanesulfonate (1.08 mL) slowly at 0 °C followed by the addition of DBU (10 mg). The solution was stirred and allowed to warm to room temperature. After complete conversion of the starting material, the reaction mixture was then concentrated in$vacuo and the crude product was taken up in 10 mL of methanol and aq. K2CO3 solution (0.72 M, 5 mL) was added. After stirring the reaction mixture for 1 h, the solution was concentrated in vacuo to give an aqu eous suspension. The suspension was diluted with the aqueous HCl solution (0.1 M, 5 mL) and the product was extracted with diethyl ether (10 mL X 2). The organic layer was then concentrated and subjected to flash column chromatography (EtOAc/hexane) on silica gel to provide 665 mg of the product 24, (92%) as an oil.

Reference： [1]Jung, Michael E.; Yi, Sung Wook [Tetrahedron Letters, 2012, vol. 53, # 32, p. 4216 - 4220]

79
[ 96-21-9 ]
[ 80522-42-5 ]
[ 1402599-30-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h;
	With N-ethyl-N,N-diisopropylamine In dichloromethane for 24h;	35.1 Step 1. A 250 mL round-bottomed flask was charged with l,3-dibromo-2- propanol (10 g, 46 mmol, Sigma- Aldrich, St. Louis, MO), dichloromethane (92 mL), N-ethyl-N-(l -methyl ethyl)-2-propanamine (24 mL, 140 mmol, EMD, Gibbstown, NJ), and tris(l-methylethyl)silyl trifluoromethanesulfonate (14 mL, 51 mmol, Sigma- Aldrich, St. Louis, MO), and then the reaction mixture was stirred for 24 h. After that time, silica gel (34 g) was added, and the volatiles were removed under a vacuum. The residue was subjected to flash chromatography on silica gel (340 g of silica gel, hexane) to give (2-bromo-l- (bromomethyl)ethoxy)(tris(l-methylethyl))silane (14 g) as a clear, colorless oil.

Reference： [1]Pennington, Lewis D.; Bartberger, Michael D.; Croghan, Michael D.; Andrews, Kristin L.; Ashton, Kate S.; Bourbeau, Matthew P.; Chen, Jie; Chmait, Samer; Cupples, Rod; Fotsch, Christopher; Helmering, Joan; Hong, Fang-Tsao; Hungate, Randall W.; Jordan, Steven R.; Kong, Ke; Liu, Longbin; Michelsen, Klaus; Moyer, Carolyn; Nishimura, Nobuko; Norman, Mark H.; Reichelt, Andreas; Siegmund, Aaron C.; Sivits, Glenn; Tadesse, Seifu; Tegley, Christopher M.; Van, Gwyneth; Yang, Kevin C.; Yao, Guomin; Zhang, Jiandong; Lloyd, David J.; Hale, Clarence; St. Jean, David J. [Journal of Medicinal Chemistry, 2015, vol. 58, # 24, p. 9663 - 9679]
[2]Current Patent Assignee: AMGEN INC - WO2012/138776, 2012, A1 Location in patent: Page/Page column 123

80
[ 80522-42-5 ]
[ 143468-13-7 ]
[ 1041181-58-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 55℃; for 16h;	Step 1. In a 25 mL round-bottomed flask, <strong>[143468-13-7]6-bromo-1H-pyrrolo[2,3-b]pyridine</strong> (250 mg, 1.27 mmol, Eq: 1.00), TIPS-OTf (972 mg, 860 mul, 3.17 mmol, Eq: 2.5) and DIEA (492 mg, 665 mul, 3.81 mmol, Eq: 3) were combined with dioxane (6.25 ml) to give a light brown solution. The reaction mixture was heated to 55 C. and stirred for 16 h. The reaction mixture was poured into 20 mL EtOAc and extracted with sat NaHCO3 (3×10 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 12 g, 5% to 10% EtOAc in hexanes) to give 6-bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (380 mg, 85%) of colorless oil.

Reference： [1]Patent: US2012/295885,2012,A1 .Location in patent: Page/Page column 61-62

81
[ 31366-25-3 ]
[ 80522-42-5 ]
C₁₅H₂₄S₄Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: tetrathiafulvalene With n-butyllithium In tetrahydrofuran at -78℃; for 0.0833333h; Inert atmosphere; Stage #2: triisopropylsilyl trifluoromethanesulfonate In tetrahydrofuran at -78 - 20℃; for 1.5h; Inert atmosphere;

Reference： [1]Ueno, Ryota; Fujino, Daishi; Yorimitsu, Hideki; Osuka, Atsuhiro [Chemistry - A European Journal, 2013, vol. 19, # 22, p. 7156 - 7161]

82
[ 80522-42-5 ]
[ 1173824-58-2 ]
[ 1151529-01-9 ]
[ 1430067-47-2 ]
[ 1430067-48-3 ]
[ 1430067-49-4 ]

Yield	Reaction Conditions	Operation in experiment
53.846 % de	With 2,6-dimethylpyridine In dichloromethane at 0℃;	1-O-triisopropyl-2-deoxy-2,2-difluoro-3,5-di-O-benzoyl-D-arabinofuranose(17) To a solution of 16(8.02g, 21.2 mmol) in CH2Cl2 (100 mL) at 0 oCwas added 2,6-lutidine (2.69 mL, 23.4 mmol, 1.1 eq) and TIPS-OTf (11.42 mL,42.5 mmol, 2eq) dropwise. The reaction mixture was stirred at 0 oCfor 2h before evaporation of solvents to dryness. Purification of the residueby column chromatography (Hexane/Et2O 95/5 to 80/20) gave 17 (7.686 g, 14.3 mmol, 67% yield) as acolorless oil (ratio α/β 0.3/1) and a mixture of side products 1-O-triiospropyl-2,2-deoxy-2,2-difluoro-3or 5-O-benzoyl-D-arabinofuranose(1.352g, 3.14 mmol, 15% yield) as a colorless oil. 1H NMR (CDCl3,500 MHz): δ 8.10-8.05 (m, 3H, ArH), 8.00-7.99 (m, 2H,ArH), 7.63-7.42 (m, 6H, ArH), 7.37-7.33 (m, 2H, ArH), 5.81 (dt, J = 14.4, 7.2 Hz, 1H, H3-β), 5.47-5.44 (m, 0.6H, H1-α, H3-α), 5.36 (d, J = 6.9 Hz, 1H, H1-β), 4.72 (m, 0.6H, H5-α), 4.69 (dd, J = 11.6 Hz, 5.0 Hz, 1H, H5a-β), 4.64 (t, J = 6.4 Hz, 0.3H, H4-α), 4.56 (dd, J = 11.6 Hz, 6.2 Hz, 1H, H5b-β), 4.49 (q, J = 5.8 Hz, 1H, H4-β), 1.11 (dd, J = 13.4 Hz, 6.5 Hz, 27.3H, TIPS). Only the signals of the β compound could be seen on the carbon spectra: 13C NMR (CDCl3,125 MHz): δ 165.9 (Cq), 165.0 (Cq), 133.7 (CAr), 133.0 (CAr), 132.9(CAr), 130.0 (CAr), 129.7 (CAr), 129.5(Cq), 128.5 (Cq) 128.3 (CAr), 128.2(CAr), 121.5 (t, J = 258 Hz, C2), 96.0 (dd, J= 23.7 Hz, 38.5 Hz, C1), 76.6 (C4), 71.6 (dd, J = 16.1, 27.8 Hz, C3), 65.1 (C5), 17.6(CH3 TIPS), 17.4 (CH3 TIPS), 11.8 (CH TIPS). 19F NMR (CDCl3,471 MHz): δ -108.50 (d, J = 246 Hz, Fa-α), -122.98 (d, J= 233 Hz, Fa-β),-124.19 (d, J = 246 Hz, Fb-α), -125.14 (d, J= 233 Hz, Fb-β).

Reference： [1]Hamon, Nadege; Quintiliani, Maurizio; Balzarini, Jan; McGuigan, Christopher [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 9, p. 2555 - 2559]

83
[ 1227585-65-0 ]
[ 80522-42-5 ]
C₁₅H₂₅BrClNOSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1H-imidazole; In dichloromethane; at 20℃; for 0.0833333h;	To a solution of 52 (15.0 g, 67.4 mmol) in dichloromethane (60 mL) was added triisopropylsilyl trifluoromethanesulfonate (29.0 g, 94 mmol). The solution was cooled to 5 C and imidazole (12.0 g, 176 mmol) was added in a few portions below 20 C. The reaction mixture was stirred at room temperature for 5 mm and 5% brine (50 mL) was charged. The organic layer was separated and solvent removed under vacuum at 50 C. The resulting oil was dissolved in methanol (100 mL). The solution was kept under CO (100 psi) at 60 C for 18 h in the presence of 5 mol% of Pd(dppf)C12. The solvent was removed and the residue was transferred onto silica gel (60 g) on a filter funnel. The mixture was rinsed with a mixture of 10% ethyl acetate in hexane (400 mL). The resulting solution was concentrated to give crude 64 (29.2 g, 98% LCAP, 84% wt, 100% yield) as an oil, which was used directly in the next step without further purification. 1H NMR (CDCl3, 400 MHz): oe 8.56 (d, J= 2.4 Hz, 1H), 8.30 (d, J 2.4 Hz, 1H), 5.23 (s, 2H), 4.01 (s, 3H), 1.25 (m, 3H), 1.12 (d,J= 6.8 Hz, 18H).

Reference： [1]Patent: WO2013/169348,2013,A1 .Location in patent: Page/Page column 84

84
[ 874-89-5 ]
[ 80522-42-5 ]
[ 500024-68-0 ]

Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 3800 - 3805

85
[ 625-23-0 ]
[ 80522-42-5 ]
[ 1612763-84-4 ]

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine In dichloromethane at 0 - 20℃;

Reference： [1]Collins, Karl D.; Ruehling, Andreas; Lied, Fabian; Glorius, Frank [Chemistry - A European Journal, 2014, vol. 20, # 13, p. 3800 - 3805]

86
[ 2174-64-3 ]
[ 80522-42-5 ]
[ 1622988-38-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane at 20℃; for 12h;
96%	With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; dichloromethane at 20℃; for 12h;	2 5-methoxy-1 ,3-bis(triisopropylsilyloxy)benzene 10a Phloroglucinol-OMe 9a (100 mg, 0.71 mmol) was dissolved in dry CH2CI2 (6 mL) and dry THF (600 μΙ). Diisopropylethylamine (257 μΙ, 1 .50 mmol) and TIPS-OTf (403 μΙ_, 1 .50 mmol) were added dropwise to the solution and the reaction mixture was stirred at room temperature during 6h. Additional amount of DIPEA and TIPS-OTf were added to reach completion of the reaction. After 6h of reaction, AcOEt (15 mL) was added to the mixture and the organic layer was washed with water (10 mL) and brine (10 mL). The organic phase was dried (MgS04) and concentrated under vacuum. The residue obtained was purified by chromatography on silica gel (hexane/ AcOEt 99/1 ) to give the di-protected phloroglucinol-OMe 10a (31 1 mg, 96%) as an uncolored oil. (0293) R, (hexane/AcOEt 95/5) 0.80; 1 H NMR (500 MHz; CDCI3) δΗ 6.09-6.08 (m, 2H, CHaro), 6.07-6.06 (m, 1 H, CHaro), 3.73 (s, 3H, CH30), 1 .27-1 .21 (m, 6H, CH-Si), 1 .10 (d, J = 7.0 Hz, 36H, (CH3)2C); 13C NMR (125 MHz; CDCI3) 5C 161 .3, 157.8, 105.0, 99.7, 55.5, 18.2, 13.0; HRMS (ESI-TOF) m/z: [M+H]+ calcd. for C25H4903Si2 453.3214; found 453.3226.

Reference： [1]Crauste, Celine; Vigor, Claire; Brabet, Philippe; Picq, Madeleine; Lagarde, Michel; Hamel, Christian; Durand, Thierry; Vercauteren, Joseph [European Journal of Organic Chemistry, 2014, vol. 2014, # 21, p. 4548 - 4561]
[2]Current Patent Assignee: UNIVERSITY OF MONTPELLIER; UNIVERSITY OF CLERMONT AUVERGNE; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; NATIONAL INSTITUTE OF HEALTH AND MEDICAL RESEARCH; CENTRE HOSPITALIER UNIVERSITAIRE DE MONTPELLIER - WO2015/162265, 2015, A1 Location in patent: Page/Page column 40

87
[ 51015-29-3 ]
[ 80522-42-5 ]
triisopropyl((6-methyl-3,4-dihydronaphthalen-1-yl)oxy)silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine; In dichloromethane; at 20℃; for 2h;Inert atmosphere;	To a solution of 20 (0.9 g, 5.3 mmol) in dry DCM (15 mL) under N2 atm was added TEA (1.3 mL, 9.0 mmol), followed by triisopropyl triflate (1.7 mL, 6.4 mmol). The reaction was stirred at room temperature for 2h, washed with cold saturated aqueous NaHCO3 (2×10 mL), dried over anhydrous Na2SO4, concentrated by rotary evaportation, and purified by column chromatography to give triisopropyl((6-methyl-3,4-dihydronaphthalen-1-yl)oxy)silane (17b) (84) 1H NMR (600 MHz, CDCl3) delta 7.41 (d, J=12.0 Hz, 1H), 7.01 (d, J=6.0 Hz, 1H), 6.94 (s, 1H), 5.11 (t, J=6.0 Hz, 1H), 2.71 (t, J=12.0 Hz, 2H), 2.32 (s, 3H), 2.29-2.26 (m, 2H), 1.30-1.24 (m, 3H), 1.12 (d, J=12.0 Hz, 18H). GC-MS (ES) for C20H32OSi [M]+ =316.

Reference： [1]Patent: US2015/105351,2015,A1 .Location in patent: Paragraph 0449
[2]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 1259 - 1262

88
[ 591-11-7 ]
[ 80522-42-5 ]
[ 203131-20-8 ]

Reference： [1]Synlett,2015,vol. 26,p. 1710 - 1714
[2]Organic Letters,2016,vol. 18,p. 6284 - 6287

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[ CAS No. 80522-42-5 ] {[proInfo.proName]}

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