915095-89-5|(S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran| Ambeed

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Quality Control of [ 915095-89-5 ] Purity: 97% SDS Specification

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Product Details of [ 915095-89-5 ]

CAS No. :	915095-89-5
Formula :	C₁₇H₁₆BrClO₂
M.W :	367.67
SMILES Code :	ClC1=CC=C(Br)C=C1CC2=CC=C(O[C@@H]3COCC3)C=C2
MDL No. :	MFCD27920793
InChI Key :	HUNLNKBDQXGMAP-INIZCTEOSA-N
Pubchem ID :	15941217

Safety of [ 915095-89-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 915095-89-5 ]

* 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.

Downstream synthetic route of [ 915095-89-5 ]

[ 915095-89-5 ] Synthesis Path-Downstream 1~35

2
[ 915095-84-0 ]
[ 915095-89-5 ]

Yield	Reaction Conditions	Operation in experiment
88.5%	With aluminum (III) chloride; sodium tetrahydroborate; In tetrahydrofuran; at 0 - 60℃; for 24.5h;	The solid obtained above (27.7 g, 72.6 mmol) was added to tetrahydrofuran (150 mL) and dissolved to dissolve.The liquid was cooled to 0 to 10 C. Then, sodium borohydride (4.14 g, 108.9 mmol, 1.5 eq) was added to the cooled reaction mixture, which was then batched.Aluminum trichloride (14.5 g, 108.9 mmol, 1.5 eq) was added. The resulting reaction mixture is warmed to room temperature and stirred for half an hour,Thereafter, the temperature was raised to 50 to 60 C and stirred for 24 hours. After the TLC detects that the starting point has substantially disappeared, the reaction mixture is cooled to 0 to 10 C.Then, water (50 mL) was slowly added dropwise to the reaction mixture to quench the reaction. Add ethyl acetate (200 mL×2) to the reaction quenching solution.Two times, the extracts were combined and concentrated to dryness under reduced pressure at 40-50 C. The obtained solid was used in methanol/water (1:1 by volume,100mL) was suspended and stirred at 40-50 C for 2 hours, then cooled to room temperature and stirred for 1 hour, and finally dropped to 0-10 C and stirred for 2 hours.Time. Filtration gave 23.6 g of a white solid, yield 88.5%.
84%	With aluminium trichloride; potassium borohydride; In tetrahydrofuran; at 0 - 20℃; for 0.5h;	A three-necked flask was charged with 4a (38.16 g, 100 mmol)And tetrahydrofuran (304 mL),After stirring, potassium borohydride (10.79 g, 200 mmol) was added,Cooling to 0 ~ 5 ,Aluminum trichloride (13.34 g, 100 mmol) was added in portions,Add slowly after the rise to room temperature for 30 minutes,Reheat the reaction overnight.The reaction was cooled to room temperature and quenched by adding 0.5 mol / L dilute hydrochloric acid (190 mL)The aqueous phase was extracted twice with ethyl acetate (190 mL)The organic phase saturated brine was washed twice (190 mL)Dried over sodium sulfate, concentrated and recrystallized from ethanol to give compound 5a (30.88 g, 84%).The reaction solvent tetrahydrofuran in Example 5 can be replaced by dichloromethane, 1,2_dichloroethane, toluene or 2-methyltetrahydrofuran.
81.8%	With aluminum (III) chloride; potassium borohydride; In tetrahydrofuran; at 20℃; for 6h;	Add 247 g of compound of formula 4 to the reaction flask,2L of tetrahydrofuran. Reduce the temperature to below 20 C.159 g of potassium borohydride was added at a controlled temperature.After the addition was completed, 193 g of anhydrous aluminum trichloride was added in batches at a temperature controlled below 20 C. After the addition, the reaction was refluxed for 6 hours.The TLC test was complete. The reaction solution was poured into ice water. Dilute hydrochloric acid was added dropwise. It was extracted with ethyl acetate, dried and concentrated to obtain a residue, which was purified with ethanol to obtain 193.5 g of a white compound of Formula 5 in a yield of 81.8%.

	With triethylsilane; boron trifluoride diethyl etherate; In acetonitrile; at 20℃; for 16h;Product distribution / selectivity;	To a suspension of 250 g (5-bromo-2-chloro-phenyl)-{4-[(S)-(tetrahydro-furan-3-yl)oxy]-phenyl}-methanone in 1.33 L of acetonitrile and 314 mL of triethylsilane is added 93 mL of boron trifluoride diethyl etherate at 20 C. The solution is stirred at 20 C. for 16 hours. The mixture is filtered and the filtrate is quenched with 1.5 L of 1.5 M sodium hydroxide solution at 0 to 20 C. The solvent is removed upon evaporation and the residue is diluted with 1.3 L of methyl tert-butyl ether. The product is washed with 1.2 L of 0.1 M NaOH followed by 1 L of water. The solvent is removed upon evaporation and most of the triethylsilanol is removed upon the distillation of toluene. Yield: 218 g (90% of theory) Mass spectrum (ESI+): m/z=368/370 (Cl) [M+H]+
	With sodium tetrahydroborate; trifluoroacetic acid; In dichloromethane; at 0 - 20℃; for 16h;Product distribution / selectivity;	To a suspension of 1.91 g (5-bromo-2-chloro-phenyl)-{4-[(S)-(tetrahydro-furan-3-yl)oxy]-phenyl}-methanone and 0.38 g of sodium borohydride in 10 mL of methylene chloride (or fluorobenzene alternatively) is added 5.92 g of trifluoroacetic acid at 0 C. The solution is stirred at 20 C. for 16 hours and quenched with 20 mL of water and 20 mL of MTBE at 0 to 20 C. The product is washed with 20 mL of water. The solvent is removed upon evaporation. Yield: 1.6 to 1.75 g (87 to 95% of theory)
	With sodium tetrahydroborate; trifluoroacetic acid; In Isopropyl acetate; at 0 - 20℃; for 16h;Product distribution / selectivity;	To a suspension of 1.91 g (5-bromo-2-chloro-phenyl)-{4-[(S)-(tetrahydro-furan-3-yl)oxy]-phenyl}-methanone and 0.8 g of sodium borohydride in 10 mL of isopropyl acetate is added 11.4 g of trifluoroacetic acid at 0 C. The solution is stirred at 20 C. for 16 hours and quenched with 20 mL of water and 20 mL of MTBE at 0 to 20 C. The product is washed with 20 mL of water. The solvent is removed upon evaporation. Yield: 1.6-1.75 g (87-95% of theory)
		To a solution of 0.19 g (5-bromo-2-chloro-phenyl){4-[(S)-(tetrahydro-furan-3-yl)oxy]-phenyl}-methanone in 5 mL of tetrahydrofuran is added 0.04 g of sodium borohydride at 20 C. The solution is stirred at 20 C. for 16 hours and the solvent is exchanged to 5 mL of methylene chloride. To the slurry is added 0.35 mL of 1 M boron trichloride methylene chloride solution, 0.02 mL of water and 0.24 mL of trifluoroacetic acid at 0 C., respectively. The mixture is stirred at ambient temperature for 4 hours and quenched with 10 mL of water and 10 mL of MTBE at 0 to 20 C. The product is washed with 10 mL of water. The solvent is removed upon evaporation. Yield: 0.18 g (97% of theory)
		To a suspension of 50.00 g (5-bromo-2-chloro-phenyl)-{4-[(S)-(tetrahydro-furan-3-yl)oxy]-phenyl}-methanone in 260 mL of acetonitrile and 34.68 g of dimethylethylsilane is added 20.45 g of boron trifluoride diethyl etherate at 20 IC. The solution is stirred at 20 C. for 16 hours. The mixture is filtered and the filtrate is quenched with 290 mL of 1.5 M sodium hydroxide solution at 0 to 20 C. The solvent is removed upon evaporation and the residue is diluted with 260 mL of methyl tert-butyl ether. The product is washed with 240 mL of 0.1 M NaOH followed by 200 mL of water. The solvent is removed upon evaporation and most of the dimethylethylsilanol is removed upon the distillation of heptane. Yield: 45.76 g (95% of theory) Mass spectrum (ESI+): m/z=368/370 (Cl) [M+H]+

References: [1]Organic Letters,2014,vol. 16,p. 4090 - 4093.
[2]Patent: CN108675976,2018,A .Location in patent: Paragraph 0077; 0078; 0082.
[3]Patent: CN106905305,2017,A .Location in patent: Paragraph 0056; 00057; 0058; 0059.
[4]Patent: CN110698467,2020,A .Location in patent: Paragraph 0075-0078.
[5]Patent: US2006/258749,2006,A1 .Location in patent: Page/Page column 24-25.
[6]Patent: US2006/258749,2006,A1 .Location in patent: Page/Page column 25.
[7]Patent: US2006/258749,2006,A1 .Location in patent: Page/Page column 25.
[8]Patent: US2006/258749,2006,A1 .Location in patent: Page/Page column 25.
[9]Patent: US2006/258749,2006,A1 .Location in patent: Page/Page column 25.

3
[ 915095-89-5 ]
[ 32469-28-6 ]
C₃₅H₅₉ClO₇Si₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 5.5 mL 2.0 M BuMgCl in THF in 30 mL of tetrahydrofuran is added 12 mL of 2.5 M BuLi in hexane at -15 to -5 C. and stirred at -10 C. for 20 minutes. 10.00 g of (S)-3-4-(5-bromo-2-chloro-benzyl)-phenoxy]-tetrahydrofuran in 10 mL of THF is added at -23 to -20 C. and stirred at -22 C. for 20 min. 20.32 g of 2,3,4,6-tetrakis-O-(trimethylsilyl)-D-glucopyranone in 7 mL of THF is added at -20 to -18 C. The reaction is then stirred at -20 C. for 1 hour and warmed to -12 C. in another hour. 60 mL of 25 weight-% aqueous NH4Cl solution is added to quench the reaction. 40 mL of MTBE is added and the organic layer is separated. The aqueous layer is extracted with 30 mL of EtOAc. The combined organic phases are dried over MgSO4 and concentrated.
		To a solution of 5.5 mL 2.0 M BuMgCl in THF in 30 mL of tetrahydrofuran is added 12 mL of 2.5 M BuLi in hexane at -15 to -5 C. and stirred at -10 C. for 20 minutes. 10.00 g of (S)-3-4-(5-bromo-2-chloro-benzyl)-phenoxy]-tetrahydrofuran in 10 mL of THF is added at -23 to -20 C. and stirred at -22 C. for 20 min. 20.32 g of 2,3,4,6-tetrakis-O-(trimethylsilyl)-D-glucopyranone in 7 mL of THF is added at -20 to -18 C. The reaction is then stirred at -20 C. for 1 hour and warmed to -12 C. in another hour. 60 mL of 25 weight-% aqueous NH4Cl solution is added to quench the reaction. 40 mL of MTBE is added and the organic layer is separated. The aqueous layer is extracted with 30 mL of EtOAc. The combined organic phases are dried over MgSO4 and concentrated.
		To a solution of 5.5 mL 2.0 M BuMgCl in THF in 30 mL of tetrahydrofuran is added 12 mL of 2.5 M BuLi in hexane at -15 to -5 C. and stirred at -10 C. for 20 minutes. 10.00 g of (S)-3-4-(5-bromo-2-chloro-benzyl)-phenoxy]-tetrahydrofuran in 10 mL of THF is added at -23 to -20 C. and stirred at -22 C. for 20 min. 20.32 g of 2,3,4,6-tetrakis-O-(trimethylsilyl)-D-glucopyranone in 7 mL of THF is added at -20 to -18 C. The reaction is then stirred at -20 C. for 1 hour and warmed to -12 C. in another hour. 60 mL of 25 weight-% aqueous NH4Cl solution is added to quench the reaction. 40 mL of MTBE is added and the organic layer is separated. The aqueous layer is extracted with 30 mL of EtOAc. The combined organic phases are dried over MgSO4 and concentrated.

To a solution of 2.90 g (S)-3-[4-(5-bromo-2-chloro-benzyl)-phenoxy]-tetrahydrofuran in 4 mL of THF at 0 to 20 C. (or alternatively at 20 C.), is slowly charged 8.4 mL of 1.0 M i-PrMgCl/LiCl in THF. The reaction is stirred at 20 C. for 16 hours and cooled to -23 C. 4.3 g of 2,3,4,6-tetrakis-O-(trimethylsilyl)-D-glucopyranone in 2 mL of THF is added dropwise. The reaction is then stirred at -20 C. for 2 h. Aqueous NH4Cl solution (25 weight-%, 12 mL) is added to quench the reaction. MTBE (8 mL) is added and the organic layer is separated. The aqueous layer is extracted with EtOAc (30 mL). The combined organic phases are dried over MgSO4 and concentrated.

References: [1]Patent: US2006/258749,2006,A1 .Location in patent: Page/Page column 29.
[2]Patent: US2006/258749,2006,A1 .Location in patent: Page/Page column 29.
[3]Patent: US2006/258749,2006,A1 .Location in patent: Page/Page column 29.
[4]Patent: US2006/258749,2006,A1 .Location in patent: Page/Page column 29.

4
[ 21739-92-4 ]
[ 915095-89-5 ]

References: [1]Organic Letters,2014,vol. 16,p. 4090 - 4093.
[2]Patent: CN106905305,2017,A .
[3]Patent: CN110698467,2020,A .

5
[ 21900-52-7 ]
[ 915095-89-5 ]

References: [1]Organic Letters,2014,vol. 16,p. 4090 - 4093.
[2]Patent: CN110698467,2020,A .

6
[ 915095-85-1 ]
[ 915095-89-5 ]

References: [1]Organic Letters,2014,vol. 16,p. 4090 - 4093.
[2]Patent: CN108675976,2018,A .
[3]Patent: CN110698467,2020,A .

7
[ 915095-89-5 ]
[¹³C₆]-(3R,4S,5R,6R)-3,4,5-tris-trimethylsilyloxy-6-(trimethylsilyloxymethyl)tetrahydro-2H-pyran-2-one [ No CAS ]
C₂₉⁽¹³⁾C₆H₅₉ClO₈Si₄ [ No CAS ]

References: [1]Journal of labelled compounds and radiopharmaceuticals,2014,vol. 57,p. 687 - 694.

8
[ 915095-89-5 ]
[ 74372-90-0 ]
(2S,3S,4R,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)tetrahydro-2H-pyran-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Scheme 10 Under argon atmosphere <strong>[915095-89-5](S)-<strong>[915095-89-5]3-(4-(5-bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran</strong></strong> (2E, 4.10 g) is dissolved in THF (1 5 ml) and cooled to 0 C. To this solution 5.6 ml of tributyllithium magnesate solution (0.7M in ether/hexanes) is slowly added and left at 0C for 20 minutes. This solution is slowly (20 min) added to a solution of (1 S,3R,4R,5S,6R)- 4,5-bis(benzyloxy)-3-((benzyloxy)methyl)-2,7-dioxabicyclo[4.1 .0]heptane (1 A, 4.71 g) and copper cyanide dilithiumchlonde complex (1 M, 0.272 ml) in THF (8 ml). The mixture is stirred at r. t. for several hours, then quenched with saturated ammonium chloride, stirred at r. t. for another hour then extracted with ethyl acetate. Organic phase is further purified using flash column chromatography (ethyl acetate/heptane 1 :6) to give (2S,3S,4R,5R,6R)- 4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3- yl)oxy)benzyl)phenyl)tetrahydro-2H-pyran-3-ol (3E).

References: [1]Patent: WO2015/177083,2015,A1 .Location in patent: Page/Page column 28.

9
[ 864070-18-8 ]
[ 86087-24-3 ]
[ 915095-89-5 ]