[ CAS No. 22206-57-1 ] {[proInfo.proName]}

Name: 22206-57-1|Tetrabutylammonium fluoride xhydrate|85%
Brand: Ambeed
SKU: A100141
Price: 5.0 USD
Availability: InStock
Rating: 97 (40 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

2D 3D

Structure of 22206-57-1 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 22206-57-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 22206-57-1 ]

SDS Specification

Alternatived Products of [ 22206-57-1 ]

Product Details of [ 22206-57-1 ]

CAS No. :	22206-57-1	MDL No. :	MFCD00149980
Formula :	C₁₆H₃₈FNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UQCWXKSHRQJGPH-UHFFFAOYSA-M
M.W :	279.48	Pubchem ID :	16211673
Synonyms :

Calculated chemistry of [ 22206-57-1 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	12
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	85.56
TPSA :	9.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	-4.66
Log Po/w (XLOGP3) :	0.73
Log Po/w (WLOGP) :	1.94
Log Po/w (MLOGP) :	-0.04
Log Po/w (SILICOS-IT) :	4.71
Consensus Log Po/w :	0.54

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.24
Solubility :	16.1 mg/ml ; 0.0575 mol/l
Class :	Very soluble
Log S (Ali) :	-0.5
Solubility :	87.9 mg/ml ; 0.314 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-6.35
Solubility :	0.000125 mg/ml ; 0.000000449 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.83

Safety of [ 22206-57-1 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3261
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 22206-57-1 ]

* 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 [ 22206-57-1 ]

[ 22206-57-1 ] Synthesis Path-Downstream 1~88

1
[ 15288-70-7 ]
[ 22206-57-1 ]
Tetrabutylammoniumsalz der Diphenylthiophosphinsaeure [ No CAS ]

Reference： [1]Phosphorus and Sulfur and the Related Elements,1981,vol. 11,p. 349 - 356

2
[ 128060-30-0 ]
[ 22206-57-1 ]
[ 121512-96-7 ]
[ 128060-37-7 ]
[ 128060-34-4 ]
[ 128060-33-3 ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 7523 - 7544

3
[ 128060-30-0 ]
[ 22206-57-1 ]
[ 121512-96-7 ]
[ 128060-34-4 ]
[ 128060-33-3 ]
[ 128090-32-4 ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 7523 - 7544
[2]Tetrahedron,1989,vol. 45,p. 7523 - 7544

4
[ 128060-30-0 ]
[ 22206-57-1 ]
[ 128060-37-7 ]
[ 128060-33-3 ]
[ 128060-35-5 ]
[ 128090-32-4 ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 7523 - 7544

5
[ 128060-30-0 ]
[ 22206-57-1 ]
[ 128060-34-4 ]
[ 128060-33-3 ]
[ 128060-35-5 ]
[ 128090-32-4 ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 7523 - 7544

6
[ 22206-57-1 ]
[ 128060-44-6 ]
[ 128060-34-4 ]
[ 128060-33-3 ]
[ 128060-48-0 ]
[ 128060-35-5 ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 7523 - 7544
[2]Tetrahedron,1989,vol. 45,p. 7523 - 7544

7
[ 22206-57-1 ]
[ 128060-44-6 ]
[ 128060-34-4 ]
[ 128060-33-3 ]
[ 128060-48-0 ]
[ 128090-32-4 ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 7523 - 7544

8
[ 22206-57-1 ]
[ 128060-45-7 ]
[ 128060-52-6 ]
[ 128090-34-6 ]
[ 128060-50-4 ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 7523 - 7544

9
[ 22206-57-1 ]
[ 128060-46-8 ]
[ 128060-54-8 ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 7523 - 7544

10
[ 22206-57-1 ]
Thiophosphoric acid O-(2-chloro-phenyl) ester S-ethyl ester O'-[(1S,3R,3aR,6aS)-3-(6-[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-purin-9-yl)-5,5-dimethyl-hexahydro-cyclopenta[c]furan-1-ylmethyl] ester [ No CAS ]
6-N-(4-methoxytrityl)-2',3'-O-isopropylideneadenosine-5'-phosphoromonofluoridate n-tetrabutylammonium salt [ No CAS ]

Reference： [1]Tetrahedron,1989,vol. 45,p. 7523 - 7544

11
[ 22206-57-1 ]
[ 80358-36-7 ]
Tetrabutylammoniumsalz der Diphenylphosphinsaeure [ No CAS ]

Reference： [1]Phosphorus and Sulfur and the Related Elements,1981,vol. 11,p. 349 - 356

12
Phenyl 2-O-(3-O-benzyl-4,6-O-benzylidene-2-O-tertbutyldimethylsilyl-β-D-mannopyranosyl)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside [ No CAS ]
[ 22206-57-1 ]
Phenyl 2-O-(3-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In tetrahydrofuran;	5) Phenyl 2-O-(3-O-benzyl-4,6-O-benzylidene-beta-D-mannopyranosyl)-3-O-benzyl-4,6-O-benzylidene-1-thio-alpha-D-mannopyranoside (6) 3.8 g (4.2 mmol, 1 eq) of product 5 and 6.6 g (21 mmol, 5 eq) of tetrabutyl-ammonium trihydrate fluoride were dissolved in 60 ml of tetrahydrofuran. After 1 hour at ambient temperature, the medium was diluted with dichloromethane and the organic phase was washed with water. The organic phase was dried over magnesium sulfate, filtered and evaporated under reduced pressure. Silica gel chromatography (elution: cyclohexane/ethyl acetate=3/1) yielded 6 (3.0 g, 90percent) in the form of a white powder. m.p.: 79-81° C. (hexane); (alpha)D+30 (c 0.33, chloroform). 1H-NMR (400 MHz, CDCl3): delta7.54-7.30 (m, 25H, arom.), 5.59 and 5.51 (2s, 2H, by), 5.54 (d, 1H, J1-2=1 Hz, H-1A), 4.89 (d, 1H, Jgem=12.2 Hz, CHPh), 4.86 (d, 1H, Jgem=11.8 Hz, CHPh), 4.82 (d, 1H, Jgem=11.8 Hz, CHPh), 4.8 (d, 1H, Jgem=12.2Hz, CHPh), 4.77 (d, 1H, J1-2=0.8 Hz, H-1B), 4.66 (dd, 1H, J2-1=1 Hz and J2-3=3.3 Hz, H-2A), 4.33 (dt, 1H, J5-4=9.7 Hz and J5-6a=J5-6b=4.9 Hz, H-5A), 4.32 (t, 1H, J4-3=J4-5=9.3 Hz, H-4B), 4.26 (dd, 1H, J6b-6a=10.5 Hz, and J6b-5a=4.9 Hz, H-6Bb), 4.3 (dd, 1H, J6b-6a=10 Hz and J6b-5=5 Hz, H-6Ab), 4.24 (t, 1H, J4-3=J4-5=9.7 Hz, H-4A), 4.19 (bd, 1H, J2-3=3.9 Hz, H-2B), 4.04 (dd, 1H, J3-2=3.3 Hz and J3-4=9.7 Hz, H-3A), 3.8 (m, 2H, H-6Aa and H-6Ba), 3.72 (dd, 1H, J3-2=3.9 Hz and J3-4=9.2 Hz, H-3B), 3.43 (dt, 1H, J5-4=J5-6a=9.5 Hz and J5-6b=4.9 Hz, H-5B), 3.2 (br, 1H, OH). 13C-NMR (100 MHz): delta138, 137.8, 137.3, 137.29, 131.7 (5 C arom.), 129.2-127.7 (25 CH arom.), 101.4 (CH by), 101.2 (CH by), 97.4 (1JCH=163 Hz, C-1B), 86.4 (1JCH=167 Hz, C-1A), 78.5 (C-4A), 78.4 (C-4B), 76.1 (C-3B), 74.4 (C-3A), 74.35 (C-2A), 72.4 (CH2Ph), 72.3 (CH2Ph), 69.4 (C-2B), 68.5 (C-6B), 68.25 (C-6A), 66.8 (C-5B), 65.2 (C-5A). Mass spectrum: m/z 808 (M+NH4)+. Analysis for C46H46O10S (790.93): calculated=C: 69.85 H: 5.86; found=C: 69.76 H: 6.01.

Reference： [1]Patent: US2003/105060,2003,A1

13
[ 198758-88-2 ]
[ 22206-57-1 ]
[ 198758-90-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium chloride; sodium hydrogencarbonate; In tetrahydrofuran;	410 mg of 11a is allowed to stand in 15.9 ml of THF with 841 mg of tetrabutylammonium fluoride (trihydrate) overnight at room temperature. Then, another 420 mg of tetrabutylammonium fluoride (trihydrate) is added, and it is stirred for 5 hours. After saturated sodium bicarbonate solution and saturated sodium chloride solution are added, it is extracted with ethyl acetate. After the organic phase is dried with sodium sulfate, it is concentrated by evaporation, and the residue is chromatographed on silica gel with ethyl acetate/hexane. 110 mg of title compound 12a is obtained as a colorless oil. 1H-NMR (300 MHz, CDCl3): delta=0.57 ppm (s, 3H); 1.00 (m, 8H); 1.15 (m, 2H); 2.55 (t, 2H); 4.12 (d, 2H); 4.23 (m, 1H); 4.43 (m, 1H); 5.00 (brs, 1H); 5.32 (brs, 1H); 5.42 (dd, 1H); 5.58 (dd, 1H); 6.00 (d, 1H); 6.38 (d, 1H); 6.58 (s, 1H)

Reference： [1]Patent: US2002/49344,2002,A1

14
[ 198759-02-3 ]
[ 22206-57-1 ]
[ 198759-04-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium chloride; sodium hydrogencarbonate; In tetrahydrofuran;	210 mg of 21a is dissolved in 7 ml of THF and allowed to stand with 420 mg of tetrabutylammonium fluoride (trihydrate) overnight at room temperature under nitrogen. Then, it is poured into a mixture of saturated sodium chloride and saturated sodium bicarbonate solution (50:1), extracted with ethyl acetate, the organic phase is washed with saturated sodium chloride solution, dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 56 mg of title compound 22a is obtained as a colorless foam. 1H-NMR (300 MHz, CDCl3): delta=0.50 ppm (s, 3H); 0.98 (d, 3H); 1.05 (m, 4H); 1.25 (t, 3H); 2.74 (q, 2H); 3.97 (d, 1H); 4.23 (m, 1H); 4.43 (m, 1H); 5.00 (brs, 1H); 5.32 (brs, 1H); 5.40 (dd, 1H); 5.56 (dd, 1H); 6.00 (d, 1H); 6.38 (d, 1H); 6.65 (s, 1H)

Reference： [1]Patent: US2002/49344,2002,A1

15
[ 198759-12-5 ]
[ 198759-13-6 ]
[ 198760-05-3 ]
[ 22206-57-1 ]
(5Z,7E,22E)-(1S,3R,24S)-25-phenyl-26,27-cyclo-9,10-secocholesta-5,7,10⁽¹⁹⁾,22-tetraene-1,3,24-triol [ No CAS ]
(5Z,7E,22E)-(1S,3R,24R)-25-phenyl-26,27-cyclo-9,10-secocholesta-5,7,10⁽¹⁹⁾,22-tetraene-1,3,24-triol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium borohydrid; In tetrahydrofuran; methanol;	1.31 g of enone 33 is dissolved in 3.1 ml of THF and 7.2 ml of methanol and mixed at 0° C. under nitrogen with 7.2 ml of a 0.4 molar methanolic cerium trichloride-heptahydrate solution. Then, 200 mg of sodium borohydride is added in portions and stirred for 40 more minutes at 0° C. Ice water is now added, extracted with ethyl acetate and dried on sodium sulfate. The residue is chromatographed on silica gel with hexane/ethyl acetate, whereby in the elution sequence, 133 mg of (5Z,7E,22E)-(1S,3R,24S)-1,3-bis[[dimethyl(1,1-dimethylethyl)silyl]oxy]-25-phenyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraen-24-ol 34a and 374 mg of (5Z,7E,22E)-(1S,3R,24R)-1,3-bis[[dimethyl(1,1-dimethylethyl)silyl]oxy]-25-phenyl-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraen-24-ol 34b accumulate as colorless foams. 133 mg of 34a is allowed to stand in 5.6 ml of THF with 295 mg of tetrabutylammonium fluoride (trihydrate) overnight at room temperature under nitrogen. The reaction mixture is then stirred into ice-cold saturated sodium bicarbonate solution and extracted with ethyl acetate. The combined organic phases are washed with water, dried on sodium sulfate and concentrated by evaporation. Chromatography of the residue on silica gel with ethyl acetate/hexane yields 38 mg of title compound 35a as a colorless foam. 1H-NMR (300 MHz, CDCl3): delta=0.57 ppm (s, 3H); 0.85 (m, 4H); 1.05 (d, 3H); 3.78 (d, 1H); 4.23 (m, 1H); 4.43 (m, 1H); 5.00 (brs, 1H); 5.30 (dd, 1H); 5.32 (brs, 1H); 5.42 (dd, 1H); 6.00 (d, 1H); 6.38 (d, 1H); 7.30 (m, 5H)

Reference： [1]Patent: US2002/49344,2002,A1

16
[ 94667-54-6 ]
[ 54502-37-3 ]
[ 22206-57-1 ]
2-Ethyl-butyric Acid 8-[2-(4-Hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl Ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In tetrahydrofuran; pyridine;	EXAMPLE 1 2-Ethyl-butyric Acid 8-[2-(4-Hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl Ester To a solution of 152 mg (0.350 mmol) of 4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl)-ethyl]-tetrahydro-pyran-2-one in 2 ml of pyridine are added 927 mg (4.39 mmol) of 2-ethyl-butyric acid anhydride and the mixture is stirred overnight at room temperature. The reaction is quenched with saturated aqueous sodium bicarbonate. The aqueous phase is separated and extracted twice with methyl-t-butyl ether. The organic phases are combined, washed with a 10percent citric acid solution and dried over sodium sulfate. The crude product is dissolved in 5 ml of THF containing 75 mg (1.3 mmol) acetic acid and 0.3 g (1 mmol) of tetrabutyl ammonium fluoride trihydrate are added. After 20 hours at room temperature the reaction is quenched with saturated aqueous sodium bicarbonate. The phases are separated and the water phase is extracted twice with ethyl acetate. The organic phases are combined, washed with brine and dried over sodium sulfate. After evaporation of the solvent, the crude product is purified by silica gel chromatography (methyl-t-butyl ether) to afford the desired product which is recrystallized from diethyl ether/hexane. m.p. 120-122° C. (diethyl ether/hexane); MS (ESI) 441 (M+Na), 419 (M+H).

Reference： [1]Patent: US6630492,2003,B1

17
(3R,4R)-4-(Biphenyl-4-ylcarbonyloxy)-3-[4-(tert-butyl-dimethyl-silanyloxy)-benzoylamino]-azepane-1-carboxylic acid tert-butyl ester [ No CAS ]
[ 22206-57-1 ]
(3R,4R)-4-(Biphenyl-4-ylcarbonyloxy)-3-(4-hydroxy-benzoylamino)-azepane-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium chloride; citric acid; In tetrahydrofuran;	A. 754 mg of (3R,4R)-4-(Biphenyl-4-ylcarbonyloxy)-3-[4-(tert-butyl-dimethyl-silanyloxy)-benzoylamino]-azepane-1-carboxylic acid tert-butyl ester were dissolved in 10 ml tetrahydrofuran and 147 mg of tetrabutylammoniumfluoride trihydrate were added at 0° C. and the reaction mixture was stirred for two hours at room temperature. 2.5 ml of a saturated solution of sodium chloride and 2.5 ml of an aqueous 1 molar solution of citric acid were added. The organic layer was concentrated under vacuo diluted with ethyl acetate then washed with 5 ml of a saturated solution of sodium chloride dried over magnesium sulfate and evaporated. The crude compound was purified on silica gel (dichloromethane:ethylacetate 1:1) to yield 551 mg (89percent yield) of (3R,4R)-4-(Biphenyl-4-ylcarbonyloxy)-3-(4-hydroxy-benzoylamino)-azepane-1-carboxylic acid tert-butyl ester. MS: 531 (M+H)+; IR: 3352, 2967, 2933, 1713, 1666, 1609, 1540, 1505, 1417 cm-1

Reference： [1]Patent: US5907038,1999,A

18
[ 35714-48-8 ]
[ 81290-20-2 ]
[ 22206-57-1 ]
α-trifluoromethyl-(7-chloroquinolin-4-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrogenchloride; In tetrahydrofuran;	EXAMPLE 10 7-Chloro-alpha-(trifluoromethyl)-4-quinolinemethanol STR20 4-Carboxaldehyde-7-chloro quinoline (1.00 g, 5.22 mmol) was dissolved in 12.5 ml of a 0.5 M solution of trimethyl(trifluoromethyl)silane in tetrahydrofuran in an oven dried, nitrogen swept 100 ml round bottomed flask, and the resulting solution was cooled to 0° C. under nitrogen. With stirring, tetra-n-butyl ammonium fluoride trihydrate (0.014 g, 0.052 mmol) was added as a solid and the mixture allowed to warm slowly to room temperature over two hours by which time thin layer chromatography (hexanes:ethyl acetate/2:1) indicated complete consumption of the starting material. The reaction mixture was cooled to 0° C. and 10percent aqueous hydrochloric acid (3 ml) was added and the mixture stirred at room temperature until cleavage of the trimethyl silyl ether was complete as indicated by thin layer chromatography (1 h). The reaction mixture was partitioned between saturated sodium hydrogen carbonate and ethyl acetate, the layers separated and the aqueous layer extracted with an additional portion of ethyl acetate. The combined organic layers were dried (MgSO4) filtered and concentrated to dryness. Purification by flash silica gel chromatography (hexanes:ethyl acetate/2:1) provided 7-chloro-alpha-(trifluoromethyl)-4-quinolinemethanol (1.32 g, 96percent) as a yellow solid. An analytical sample was prepared by recrystallization from ethyl acetate:hexanes. (mp 161° C.).

Reference： [1]Patent: US6117884,2000,A

19
[ 137585-40-1 ]
[ 22206-57-1 ]
[ 137585-47-8 ]

Yield	Reaction Conditions	Operation in experiment
77%	In tetrahydrofuran; ethyl acetate; Petroleum ether;	EXAMPLE 2 6beta-Acryloyloxy-1alpha,9alpha-dihydroxy-8,13-epoxy-7beta-methoxyacetoxy-labd-14-en-11-one 6beta-Acryloyloxy-1alpha-t-butyldimethylsilyloxy-8,13-epoxy-9alpha-hydroxy-7beta-methoxyacetoxy-labd-14-en-11-one (1.38 g, 2.28 mmol) in anhydrous tetrahydrofuran (30 ml) was stirred with tetrabutyl ammonium fluoride trihydrate (0.81 g, 2.51 mmol) for half an hour at room temperature and the reaction mixture was concentrated. The residue was extracted with ethyl acetate, the organic layer was washed with brine solution, dried over anhydrous sodium sulphate and concentrated. The residue obtained was purified by flash chromatography using ethyl acetate:petroleum ether (1:4) as eluant. The compound was used as such for the next step. Yield 77percent, m.p. 176°-178° C.

Reference： [1]Patent: US5206241,1993,A

20
1-([2'R,3'R,4'S]-4'-((t-Butyldimethylsilyl)oxymethyl)-3'hydroxymethyl-2'-oxetanyl)-5-(2-iodo-1-vinyl)uracil [ No CAS ]
[ 22206-57-1 ]
1-([2'R,3'R,4'R]3',4'-Bis(hydroxymethyl)-2-oxetanyl)-5-(2-iodo-1-vinyl)uracil [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; methanol; water; acetic acid;	Step 4 1-([2'R,3'R,4'R]3',4'-Bis(hydroxymethyl)-2-oxetanyl)-5-(2-iodo-1-vinyl)uracil To a stirred solution of 206 mg (0.42 mmol) of 1-([2'R,3'R,4'S]-4'-((t-Butyldimethylsilyl)oxymethyl)-3'-hydroxymethyl-2'-oxetanyl)-5-(2-iodo-1-vinyl) uracil, the product of Step 3 of Example 49, in 2 mL THF was added 145 mg (0.46 mmol) of <strong>[22206-57-1]tetra-n-butylammonium fluoride trihydrate</strong>. The mixture was stirred at ambient temperature for 3.5 hours and 24 muL of glacial acetic acid was added. The resultant solution was concentrated under reduced pressure. The residue was taken up in 6 mL of 1:1 MeOH/H2 O and the organic solvent removed under reduced pressure at 50°. Cool the resulting aqueous mixture to 0° and harvest 114 mg (72percent) of the title compound as white crystals: Analysis calculated for C11 H13 IN2 O5: C, 34.75; H, 3.45; N, 7.37. Found: C, 35.00; H, 3.42; N, 7.33; 1 H NMR (DMSO-D6, TMS=0.00 ppm) delta3.15-3.75 (m, 6H), 4.49 (m, 1H), 4.95 (t, 1H), 5.38 (t, 1H), 6.24 (d, 1H), 7.17 (dd, 2H), 8.60 (s, 1H); DCI NH3 MS, m/z 381 (M+H)+.

Reference： [1]Patent: US5420276,1995,A

21
1([2'R,3'R,4'S]-4'-((t-Butyldimethylsilyl)oxymethyl)-3'-hydroxymethyl-2'-oxetanyl)-5-(2-chloro-1-vinyl)uracil [ No CAS ]
[ 22206-57-1 ]
[ 187652-92-2 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; acetic acid;	Step 2 1-([2'R,3'R,4'S]3',4'-Bis(hydroxymethyl)-2'-oxetanyl)-5-(2-chloro-1-vinyl)uracil To a stirred solution of 195 mg (0.48 mmol) of 1-([2'R,3'R,4'S]-4'-((t-Butyldimethylsilyl)oxymethyl)-3'-hydroxymethyl-2'-oxetanyl)-5-(2-chloro-1-vinyl)uracil, the product of Step 1 of Example 50, in 2 mL THF was added 168 mg (0.53 mmol) of <strong>[22206-57-1]tetra-n-butylammonium fluoride trihydrate</strong>. The mixture was stirred at ambient temperature for 2 hours and 28 muL of glacial acetic acid was added. The resultant solution was concentrated under reduced pressure. The residue was taken up in 1:1 MeOH/H2 O (6 mL) and the organic solvent removed under reduced pressure at 50°. Cool the resulting aqueous mixture to 0° and harvest 106 mg (76percent) of the title compound as white crystals: Analysis calculated for C11 H13 ClN2 O5: C, 45.76; H, 4.54; N, 9.71. Found: C, 45.62; H, 4.63; N, 9.50; 1 H NMR (DMSO-D6, TMS 0.00 ppm) delta3.13-3.75 (m, 6H), 4.49 (m, 1H), 4.95 (t, 1H), 5.35 (t, 1H), 6.24 (d, 1H), 6.59 (d, 1H, J=4 Hz), 7.17 (d, 1H, J=4 Hz), 8.57 (s, 1H); DCI NH 3 MS, m/z 289.291 (M+H)+.

Reference： [1]Patent: US5420276,1995,A

22
Methyl Z-[2-(2-acetamidothiazol-4-yl)-3-[trans-4-(t-butyldimethylsilyl)oxy]cyclohexyl]propenoate [ No CAS ]
[ 22206-57-1 ]
Methyl Z-[2-(2-acetamidothiazol-4-yl)-3-(trans-4hydroxy)cyclohexyl]propenoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	(d) Methyl Z-[2-(2-acetamidothiazol-4-yl)-3-(trans-4hydroxy)cyclohexyl]propenoate Methyl Z-[2-(2-acetamidothiazol-4-yl)-3-[trans-4-(t-butyldimethylsilyl)oxy]cyclohexyl]propenoate (132mg) was heated at reflux in tetrahydrofuran (5ml) with <strong>[22206-57-1]tetra-n-butylammonium fluoride trihydrate</strong> (300mg) for 20h. The dark solution was cooled, poured into water and extracted twice with ethyl acetate, then the combined organic extracts were washed with NaHC03 (aq), brine, dried and evaporated to give an orange gum (116mg). Chromatography on silica gel, eluding with ethyl acetate-hexane mixtures, afforded the hydroxy ester (69mg) (Found: M, 324.1145. C15 H20 N2 O4 S requires M, 324.1144); delta[(CD3)2 CO, 250MHz]1.15~1.40, 1.70-2.05 (8H,2m), 2.26 (3H,s), 2.47 (1H,m), 3.50 (1H,m), 3.84 (3H,s), 6.55 (1H,d,J=10Hz), 6.98 (1H,s), and 11.00 (1H,br s).

Reference： [1]Patent: US4954489,1990,A

23
Methyl Z-[2-(2-acetamidothiazol-4-yl)-3-[cis-4-(t-butyldimethylsilyl)oxy]cyclohexyl]propenoate [ No CAS ]
[ 22206-57-1 ]
Z-[2-(2-Aminothiazol-4-yl)-3-(cis-4-hydroxy)cyclohexyl]propenoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; sodium chloride;	(g) Z-[2-(2-Aminothiazol-4-yl)-3-(cis-4-hydroxy)cyclohexyl]propenoic acid Methyl Z-[2-(2-acetamidothiazol-4-yl)-3-[cis-4-(t-butyldimethylsilyl)oxy]cyclohexyl]propenoate (71mg) was desilylated using <strong>[22206-57-1]tetra-n-butylammonium fluoride trihydrate</strong> (252mg) as described in Example 8(d). After chromatography the product was at once hydrolyzed using 1M sodium hydroxide (5 equivalents) as described in Example 1(e). After acidification to pH2 with 2M HCl the aqueous phase was saturated with sodium chloride and extracted with tetrahydrofuran (4x). The combined organic extracts were dried and evaporated to give crude product which was chromatographed on silica gel, eluding with ethyl acetate:isopropanol:water mixtures, to give the acid (29mg); delta[(CD3)2 SO,250MHz]1.30-1.70 (8H,m), 2.50 (1H,m,partly solvent-obscured), 3.73 (1H,m), 6.32 (1H,d,J=10Hz), 6.38 (1H,s), and 7.01 (2H,s); m/e 224 (M--CO2+).

Reference： [1]Patent: US4954489,1990,A

24
4-(t-butyldimethylsilyl)-1-methyl piperazine [ No CAS ]
[ 68077-26-9 ]
[ 22206-57-1 ]
[ 70458-92-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	In water; acetonitrile;	EXAMPLE 2 1-Ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-methylpiperazinyl)quinoline-3-carboxylic Acid (R1: Ethyl; R2: Methyl) 0.5 g (1.85 mmol) of 1-ethyl-6-fluoro-7-chloro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (II, R1: ethyl; X: chloro) and 1.07 g (0.50 mmol) of 4-(t-butyldimethylsilyl)-1-methyl piperazine (III, R2, R3 and R4: methyl; R5: t-butyl) are added to 100 ml of acetonitrile and then heated with stirring. A solution of 1.60 g (0.50 mmol) of tetrabutyl ammonium fluoride trihydrate in 5 ml of acetonitrile is added dropwise to the reaction mixture. After heating with stirring for 3 hours,the solvent is stripped off and water is added thereto to give a solid. After filtering and drying, 0.52 g (85percent yield) of a solid compound is afforded. Melting point: 270° C. NMR(CF3 COOD)ppm: 9.35(1H, s), 8.35(1H, d, J=5H), 7.53 (1H, d, J=8H), 4.87(2H, q), 3.55-4.31 (8H, m), 3.25(3H, s), 1.8(3H, t).

Reference： [1]Patent: US5051505,1991,A

25
methanolic ammonia [ No CAS ]
(2S,3S)-N-[[3-[(1,1-dimethylethoxy)carbonyl]-2,2-dimethyl-4-(2-methylpropyl)oxazolidin-5-yl]methyl]-N-[(phenylmethoxy)carbonyl]-L-leucine [ No CAS ]
[ 3439-38-1 ]
[ 22206-57-1 ]
[ 543-27-1 ]
N-[[(3S)-3-[(1,1-Dimethylethoxy)carbonyl]-2,2-dimethyl-4-(2-methylpropyl)oxazolidin-5-yl]-methyl]-N-[(phenylmethoxy)carbonyl]-L-leucinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 4-methyl-morpholine; In tetrahydrofuran; N-methyl-acetamide; ethyl acetate;	(a) N-[[(3S)-3-[(1,1-Dimethylethoxy)carbonyl]-2,2-dimethyl-4-(2-methylpropyl)oxazolidin-5-yl]-methyl]-N-[(phenylmethoxy)carbonyl]-L-leucinamide A solution of N-[[(3S)-3-[(1,1-dimethylethoxy)carbonyl]-2,2-dimethyl-4-(2-methylpropyl)oxazolidine-5-yl]methyl]-N-[(phenylmethoxy)carbonyl]-L-leucine, 2-(trimethylsilyl)ethyl ester (379 mg., 0.597 mmole), from Example 1(j), in dimethylformamide (4 ml.) is treated with tetra-n-butyl ammonium fluoride trihydrate (414 mg., 1.31 mmole) at room temperature under argon. After 3 hours the reaction mixture is taken up in 25 ml. of ethyl acetate and 25 ml. of ether. The organic extract is rinsed with three 10 ml. portions of water, brine, dried (MgSO4), and concentrated in vacuo to give 450 mg. of crude carboxylic acid. The above carboxylic acid (0.597 mmole) is dissolved in dry tetrahydrofuran (1.8 ml.) and cooled to -25° under argon. N-methylmorpholine (60.4 g., 0.597 mmole) is added followed by the slow, careful addition of isobutylchloroformate (81.5 mg., 0.597 mmole). After 5 minutes 7N methanolic ammonia (0.358 ml., 2.51 mmole) is slowly added dropwise. The external bath temperature is allowed to warm to -10° over a period of 30 minutes, then the reaction is stoppered and left in a refrigerator overnight. The reaction is next diluted with 60 ml. of 1:1 ethyl acetate:ether and rinsed with two 10 ml. portions of water, 10 ml. of 5percent potassium bisulfate, water and brine, dried (MgSO4), and concentrated in vacuo to give 500 mg. of crude product.

Reference： [1]Patent: US4616088,1986,A

26
[ 95265-69-3 ]
[ 22206-57-1 ]
1-allyl-3-(S)-hydroxymethyl-4-(R)-tert.-butylsulphonyl-2-azetidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; hexane; ethyl acetate;	Example 12 1-allyl-3-(S)-hydroxymethyl-4-(R)-tert.-butylsulphonyl-2-azetidinone A solution of 197 mg (0.757 mmol) of N-allyl-N-tert.-butylsulphonylmethyl-(R)-glycidic acid amide in 1 ml of tetrahydrofuran is introduced at 0°, with the exclusion of moisture, into 8 ml of a tetra-n-butyl; ammonium fluoride/THF solution which has been prepared from 5.0 g of <strong>[22206-57-1]tetra-n-butylammonium fluoride trihydrate</strong> by dehydrating at 60° C./0.1 torr and making up to 20 ml with tetrahydrofuran. The reaction mixture is stirred for 2 hours at room temperature and then partitioned between methylene chloride and phosphate buffer solution (pH 8.0). The crude product obtained by drying over sodium sulphate and concentration by evaporation of the organic phase is chromatographed over preparative silica gel plates using hexane/ethyl acetate (1:3). the title compound is obtained in the form of colourless crystals. M.p. 99°-103°; Rf (hexane/ethyl acetate 1:3): 0.18; [alpha]=46+-1° (1.30percent in CHCl3); 1 H-NMR spectrum: delta=4.96 for proton (a) at the 4-(R)-carbon atom and delta=3.72 for proton (b) at the 3-(S)-carbon atom (trans-compound), J a-b: approximately 2.

Reference： [1]Patent: US4614614,1986,A

27
[ 95266-13-0 ]
[ 22206-57-1 ]
1-allyl-3-(S)-hydroxymethyl-4-(R)-phenylsulphonyl-2-azetidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; ethyl acetate;	Example 16 1-allyl-3-(S)-hydroxymethyl-4-(R)-phenylsulphonyl-2-azetidinone 8 ml of a tetra-n-butylammonium fluoride/THF solution which has been prepared from 5 g of <strong>[22206-57-1]tetra-n-butylammonium fluoride trihydrate</strong> by drying at 60°/0.1 torr and making up to 20.0 ml with tetrahydrofuran is added to a solution of 201 mg (0.757 mmol) of N-allyl-N-phenylsulphonylmethyl-(R)-glycidic acid amide in 1 ml of tetrahydrofuran. The resulting reaction mixture is stirred for 2 hours at 0° and then partitioned between methylene chloride and phosphate buffer solution having a pH of 8.0. The crude product isolated from the organic layer by means of concentration by evaporation is chromatographed over preparative silica gel plates in ethyl acetate/hexane (2:1) and the title compound is obtained in the form of a colourless oil. Rf (hexane: ethyl acetate 1:2): 0.19; IR (CH2 Cl2) 3600-3250 (with a maximum at 3590), 3050, 2910, 2850, 1763, 1440, 1375, 1320, 1305, 1250 (sh), 1145, 1082, 1032, 940; NMR spectrum: delta=4.83 for proton (a) at the 4-(R)-carbon atom and delta=3.52 for proton (b) at the 3-(S)-carbon atom (trans-compound), J a-b: approximately 2.

Reference： [1]Patent: US4614614,1986,A

28
[ 95298-67-2 ]
[ 22206-57-1 ]
1-(2,4-dimethoxybenzyl)-3-(S)-hydroxymethyl-4-(R)-tert.-butylsulphonyl-2-azetidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrabutyl ammonium fluoride;molecular sieve; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; toluene;	Example 20 1-(2,4-dimethoxybenzyl)-3-(S)-hydroxymethyl-4-(R)-tert.-butylsulphonyl-2-azetidinone To a solution of 3.35 g (9.0 mmol) of N-2,4-dimethoxybenzyl-N-tert.-butylsulphonylmethyl-(R)-glycidic acid amide in 14 ml of tetrahydrofuran there are added at 0°, with the exclusion of moisture, 53 ml of a solution of tetra-n-butylammonium fluoride in THF which has been prepared from 20 g of <strong>[22206-57-1]tetra-n-butylammonium fluoride trihydrate</strong> (Fluka) by dehydrating at 60°/0.1 torr and making up to 80 ml with tetrahydrofuran. 50 g of molecular sieve freshly activated at 0.1 torr (type 4A 1/16, Messrs. Dr. Bender and Dr. Hobein) are added to the reaction mixture and the whole is stirred for 2 hours at 0°. The molecular sieve is filtered off and washed with 360 ml of methylene chloride and the combined filtrates are washed, after the addition of 1.8 liters of diethyl ether, with 200 ml of a phosphate buffer solution having a pH of 8.0. After distilling off the organic solvent, the residue is chromatographed over 110 g of silica gel using toluene/ethyl acetate (2:1) and (1:1). The title compound is obtained which, after recrystallisation from methylene chloride/ether/pentane, forms white crystals. M.p. 124°-125°; [alpha]=+10+-1° (1.09percent in CHCl3); 1 H-NMR spectrum: delta=4.61 for proton (a) at the 4-(R)-carbon atom and delta=3.69 for proton (b) at the 3-(S)-carbon atom (trans-compound), J a-b: approximately 2.

Reference： [1]Patent: US4614614,1986,A

29
[ 95265-86-4 ]
[ 22206-57-1 ]
1-p-methoxybenzyl-3-(S)-hydroxymethyl-4-(R)-tert.-butylsulphonyl-2-azetidinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrabutyl ammonium fluoride;molecular sieve; In tetrahydrofuran;	Example 32 1-p-methoxybenzyl-3-(S)-hydroxymethyl-4-(R)-tert.-butylsulphonyl-2-azetidinone A solution of dehydrated tetra-n-butylammonium fluoride in tetrahydrofuran, which is prepared from <strong>[22206-57-1]tetra-n-butylammonium fluoride trihydrate</strong> by drying at 55°-60°/0.1 mm and dissolving in 40 ml of tetrahydrofuran, is added dropwise at 0° to a solution of 1.426 g (3.38 mmol) of N-p-methoxybenzyl-N-tert.-butylsulphonylmethyl-2-(S)-bromo-3-hydroxypropionic acid amide in 6 ml of tetrahydrofuran. Activated molecular sieve (4 A) is added to the reaction mixture and the whole is stirred for 2 hours at 0°. The molecular sieve is filtered off and washed with methylene chloride; 600 ml of ether and 75 ml of buffer solution having a pH of 8 are added to the combined filtrates. After drying over sodium sulphate and concentration by evaporation in vacuo, the crude product is obtained which is purified by chromatography over 50 g of silica gel using toluene:ethyl acetate (4:1) and (2:1).

Reference： [1]Patent: US4614614,1986,A

30
[ 95265-90-0 ]
[ 22206-57-1 ]
[ 95265-91-1 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrabutyl ammonium fluoride; In tetrahydrofuran; diethyl ether; dichloromethane;	(e) (3S,4R)-1-p-methoxybenzyl-3-[(1'R)-1-hydroxyethyl]-4-tert.-butylsulphonyl-2-azetidinone To a solution of 398 mg (1.12 mmol) of (2R,3R)-N-p-methoxybenzyl-N-tert.-butylsulphonylmethyl-2,3-epoxybutyramide in 2.5 ml of tetrahydrofuran there are added dropwise, while stirring at 0° with the exclusion of moisture, 7 ml of a solution of dehydrated tetra-n-butylammonium fluoride in THF, prepared by dehydrating 5 g of <strong>[22206-57-1]tetra-n-butylammonium fluoride trihydrate</strong> at 55° and 0.1 torr and making up to 20 ml with tetrahydrofuran. Activated molecular sieve of 4A is added to the reaction mixture and the whole is stirred for two hours. The molecular sieve is filtered off with suction and washed four times with 20 ml of methylene chloride each time. 5 parts of diethyl ether are added to each individual filtrate and the filtrates are washed in succession with aqueous phosphate buffer solution of pH 8. The combined organic phases are dried over magnesium sulphate and concentrated by evaporation under reduced pressure. The residue is chromatographed over 20 g of silica gel with toluene/ethyl acetate (3:1) and the crystalline title compound is obtained. M.p. 112°-113° (Kofler, from methylene chloride, diethyl ether, pentane); Rf (toluene/ethyl acetate 1:1): 0.27; [alpha]=+9+- 1° (1.105percent in chloroform); 1 H-NMR spectrum (400 MHz in CDCl3): delta=4.65 for proton (a) at the 4(R)-carbon atom, delta=3.61 for proton (b) at the 3(S)-carbon atom and delta=4.09 for proton (c) at the 1'(R)-carbon atom of the hydroxyethyl group; J a-b: approximately 2, J b-c: approximately 7.

Reference： [1]Patent: US4656165,1987,A

31
[ 928-90-5 ]
[ 27329-74-4 ]
[ 22206-57-1 ]
[ 106-93-4 ]
[ 113101-57-8 ]

Yield	Reaction Conditions	Operation in experiment
5.38 g (30%)	With magnesium; pyridinium chlorochromate; In tetrahydrofuran;	Example 10 Synthesis of 4-(1'-hydroxy-5'-hexynyl)-2,6-di-tert-butylphenol A mixture of 3.0 g (120 mmol) of magnesium, 25.7 g (72.0 mmol) of 2,6-di- t -butyl-4-bromo-1-trimethylsiloxybenzene and a few drops of 1,2-dibromoethane in 350 mL THF is heated at reflux for two hours and then is cooled to -78° and to it is added 5.78 g (60.0 mmol) of 5-hexynal (which is prepared from the oxidation of 5-hexyn-1-ol using pyridinium chlorochromate). The reaction mixture is stirred at -78° for 15 minutes and then is allowed to warm to 0°, where it is stirred for an additional 30 minutes. The mixture is poured into sat. NH4Cl and the aqueous layer is extracted with pentane. The combined organic phase is washed with sat. NaCl and dried (MgSO4). The crude silylated intermediate is concentrated, dissolved in 300 mL of THF, and treated at room temperature with 28.5 g (90.0 mmol) of tetra- n -butyl-ammonium fluoride trihydrate. After stirring the mixture at 25° for one hour, it is poured into sat. NH4Cl and the layers are separated. The aqueous portion is extracted with pentane and the combined organic phase is washed with sat. NaCl and then dried (MgSO4). The concentrate is purified by flash chromatography (10percent EtOAc/hexane, Rf=0.16) and recrystallization (hexane) to afford 5.38 g (30percent) of the title compound: mp 70-71°; IR (CCl4) 3620(s), 3310(m), 2960(s), 1430(s), 1160(s), 630(m) cmmin1; 1H-NMR (CDCl3)delta(ppm) 1.40(s, 18H), 1.5-2.3(m, 8H), 4.50(t, 1H), 5.15(s, 1H), 7.10(s, 2H); 13C-NMRdelta18.09, 24.88, 30.19, 34.22, 37.69, 68.51, 74.37, 84.25, 122.46, 135.16, 135.75, 153.04 ppm.
5.38 g (30%)	With magnesium; pyridinium chlorochromate; In tetrahydrofuran;	EXAMPLE 10 Synthesis of 4-(1'-hydroxy-5'-hexynyl)-2,6-di-tert-butylphenol STR24 A mixture of 3.0 g (120 mmol) of magnesium, 25.7 g (72.0 mmol) of 2,6-di-t-butyl-4-bromo-1-trimethylsiloxybenzene and a few drops of 1,2-dibromoethane in 350 mL THF is heated at reflux for two hours and then is cooled to -78° and to it is added 5.78 g (60.0 mmol) of 5-hexynal (which is prepared from the oxidation of 5-hexyn-1-ol using pyridinium chlorochromate). The reaction mixture is stirred at -78° for 15 minutes and then is allowed to warm to 0°, where it is stirred for an additional 30 minutes. The mixture is poured into sat. NH4 Cl and the aqueous layer is extracted with pentane. The combined organic phase is washed with sat. NaCl and dried (MgSO4). The crude silylated intermediate is concentrated, dissolved in 300 mL of THF, and treated at room temperature with 28.5 g (90.0 mmol) of <strong>[22206-57-1]tetra-n-butylammonium fluoride trihydrate</strong>. After stirring the mixture at 25° for one hour, it is poured into sat. NH4 Cl and the layers are separated. The aqueous portion is extracted with pentane and the combined organic phase is washed with sat. NaCl and then dried (MgSO4). The concentrate is purified by flash chromatography (10percent EtOAc/hexane, Rf =0.16) and recrystallization (hexane) to afford 5.38 g (30percent) of the title compound: mp 70°-71°; IR (CCl4) 3620(s), 3310(m), 2960(s), 1430(s), 1160(s), 630(m) cm-1; 1 H-NMR (CDCl3)delta(ppm) 1.40(s, 18H), 1.5-2.3(m, 8H), 4.50(t, 1H), 5.15(s, 1H), 7.10(s, 2H); 13 C-NMRdelta18.09, 24.88, 30.19, 34.22, 37.69, 68.51, 74.37, 84.25, 122.46, 135.16, 135.75, 153.04 ppm.

Reference： [1]Patent: EP251408,1991,B1
[2]Patent: US4708966,1987,A

32
[ 241151-38-2 ]
[ 22206-57-1 ]
[ 241151-39-3 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	g 3,3-Dimethyl-7-(tetrahydro-pyran-2-yloxy)-heptan-1-ol 10.17 g of tert-Butyl-[3,3-dimethyl-7-(tetrahydro-pyran-2-yloxy)-heptyloxy]-dimethyl-silane (28.4 mmol) was treated with 3 eq. of dry tetrabutylammoniumfluoride trihydrate (0.3M in tetrahydrofurane). After 90 Min. at room temperature, the mixture was poured onto crushed ice/ether. Usual workup followed by flash chromatography (SiO2, hexane/ethylacetate=7/3) gave 6.28 g of the title compound as colourless oil.

Reference： [1]Patent: US6184422,2001,B2

33
[ 11113-50-1 ]
[ 22206-57-1 ]
(dihydroxy)difluoroborate [ No CAS ]
hydroxotrifluoroborate [ No CAS ]

Reference： [1]Polyhedron,1997,vol. 16,p. 2499 - 2507

34
[ 14320-04-8 ]
[ 22206-57-1 ]
[ 94629-48-8 ]

Reference： [1]Zeitschrift fur Anorganische und Allgemeine Chemie,
Zeitschrift fuer Anorganische und Allgemeine Chemie,1984,vol. 517,p. 149 - 160

35
[ 55428-47-2 ]
[ 22206-57-1 ]
[ 76402-68-1 ]

Reference： [1]Inorganic Chemistry,1983,vol. 22,p. 2787 - 2789

36
[ 12582-61-5 ]
[ 22206-57-1 ]
[ 110-83-8 ]
[ 930-68-7 ]
[ 76402-68-1 ]
[ 286-20-4 ]
[ 822-67-3 ]

Reference： [1]Inorganic Chemistry,1989,vol. 28,p. 4559 - 4561

37
[ 6737-42-4 ]
[ 22206-57-1 ]
palladium dichloride [ No CAS ]
[ 31989-49-8 ]

Reference： [1]Organometallics,1990,vol. 9,p. 864 - 865

38
nickel(II) bromide dimethoxyethane [ No CAS ]
[ 6737-42-4 ]
[ 22206-57-1 ]
nickel(II) fluoride [ No CAS ]

Reference： [1]Organometallics,1992,vol. 11,p. 2212 - 2220

39
(p-OMeTPP)FeF [ No CAS ]
[ 22206-57-1 ]
[ 86646-34-6 ]

Reference： [1]Inorganic Chemistry,1983,vol. 22,p. 2787 - 2789

40
[ 79623-69-1 ]
[ 22206-57-1 ]
[ 86646-34-6 ]
(p-OMeTPP)FeF [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 6384 - 6390

41
[ 72319-58-5 ]
[ 22206-57-1 ]
[ 55428-47-2 ]
(TPP)Fe(F)(O) [ No CAS ]
(TPP)Fe(F)(ClO₄) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 6384 - 6390

42
[ 1983-10-4 ]
[ 22206-57-1 ]
tetrabutylammonium tributyldifluorostannate [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,1989,vol. 371,p. 145 - 154

43
[ 149073-14-3 ]
[ 22206-57-1 ]
[ 149039-24-7 ]

Reference： [1]Chemische Berichte,1993,vol. 126,p. 399 - 404

44
[ 16456-81-8 ]
[ 22206-57-1 ]
(Bu₄N)((TPP)FeF) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1989,vol. 111,p. 6558 - 6562

45
[ 16591-56-3 ]
[ 22206-57-1 ]
(TPP)FeF^(1-) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1989,vol. 111,p. 6558 - 6562
[2]Journal of the American Chemical Society,1989,vol. 111,p. 6558 - 6562
[3]Journal of the American Chemical Society,1989,vol. 111,p. 6558 - 6562
[4]Journal of the American Chemical Society,1989,vol. 111,p. 6558 - 6562

46
[ 125963-04-4 ]
[ 22206-57-1 ]
[ 180985-82-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999),1991,p. 501 - 508

47
[ 125963-07-7 ]
[ 22206-57-1 ]
[ 125963-08-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999),1991,p. 501 - 508

48
[ 23842-04-8 ]
[ 22206-57-1 ]
[ 57384-26-6 ]
(dihydroxy)difluoroborate [ No CAS ]
HOBHF₂^(1-) [ No CAS ]
tetrafluoroborate ion [ No CAS ]
hydroxotrifluoroborate [ No CAS ]

Reference： [1]Polyhedron,1997,vol. 16,p. 2499 - 2507

49
[ 23854-17-3 ]
[ 22206-57-1 ]
[ 57384-26-6 ]
(dihydroxy)difluoroborate [ No CAS ]
HOBHF₂^(1-) [ No CAS ]
tetrafluoroborate ion [ No CAS ]
hydroxotrifluoroborate [ No CAS ]

Reference： [1]Polyhedron,1997,vol. 16,p. 2499 - 2507

50
[ 61085-06-1 ]
[ 22206-57-1 ]
(OEP)FeF^(1-) [ No CAS ]

51
[ 134495-44-6 ]
[ 22206-57-1 ]
[ 125963-06-6 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999),1991,p. 501 - 508

52
[ 134495-40-2 ]
[ 22206-57-1 ]
[ 180985-82-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999),1991,p. 501 - 508

53
[ 93403-16-8 ]
[ 22206-57-1 ]
[ 126823-77-6 ]

Reference： [1]Organometallics,1990,vol. 9,p. 1949 - 1953

54
[ 124535-63-3 ]
[ 22206-57-1 ]
[ 126823-74-3 ]

Reference： [1]Organometallics,1990,vol. 9,p. 1949 - 1953

55
[ 134495-42-4 ]
[ 22206-57-1 ]
[ 134495-41-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999),1991,p. 501 - 508

56
[ 134495-43-5 ]
[ 22206-57-1 ]
[ 134495-41-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999),1991,p. 501 - 508

57
[ 134495-22-0 ]
[ 22206-57-1 ]
[ 132405-33-5 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999),1991,p. 501 - 508

58
[ 753-73-1 ]
[ 22206-57-1 ]
trans-{Me₂SnF₄}^(2-) [ No CAS ]