CAS No.915095-89-5,Furan, 3-[4-[(5-broMo-2-chlorophenyl)Methyl]phenoxy]tetrahydro-, (3S)- Suppliers

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Items Standard Result Assay (Ursolic acid) 98%min 98.22% -----------------------------------------------------------------------------------------------------------

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(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydro-furan -- CHemwill

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Name (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydro-furan Other name (S)-3-(4-(5-Bromo-2-chlorobenzyl)phenoxy)tetrahydrofuran; (3S)-3-[4-[(5-bromo-2-ch

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(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydro-furan CAS: 915095-89-5 Specification Product name Empagliflozin Intermediate (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran

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Wuhan Zenuo Biological Medicine Technology Co Ltd

Product Name: Furan, 3-[4-[(5-broMo-2-chlorophenyl)Methyl]phenoxy]tetrahydro-, (3S)- Synonyms: 915085-89-5;EMpagliflozin int3;Furan, 3-[4-[(5-broMo-2-chlorophenyl)Methyl]phenoxy]tetrahydro-, (3S)-;(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenox

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Triumph International Development Limilted

Appearance:white or light yellow crystalline powder Storage:Store in a cool,dry place and keep away from direct strong light Package:As customer request Application:Used for research and industrial manufacture. Transportation:By

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Synthetic route

: 915095-84-0
(S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
With aluminum (III) chloride; hydrogen In toluene at 20 - 25℃; for 3h; Temperature;	95%
With aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane In toluene at 0 - 23℃; for 2.5h;	92%
With aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane In toluene at 0 - 23℃;	91.28%

: 4-bromo-2-(4-fluorobenzyl)chlorobenzene

: 86087-23-2
(S)-3-hydroxytetyrahydrofurane

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 0 - 10℃; for 1h; Inert atmosphere; Large scale;	88%

: 4-bromo-1-chloro-2-(chloromethyl)benzene

: (S)-3-phenoxytetrahydrofuran

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Stage #1: 4-bromo-1-chloro-2-(chloromethyl)benzene; (S)-3-phenoxytetrahydrofuran In ethyl acetate for 0.5h; Cooling with ice; Large scale; Stage #2: With aluminum (III) chloride In ethyl acetate at 78℃; for 8.5h; Cooling with ice; Large scale;	87%

: (S)-3-phenoxytetrahydrofuran

: 149965-41-3
5-Bromo-2-chlorobenzyl bromide

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
With aluminum (III) chloride In ethyl acetate at 78℃; for 9h; Cooling with ice; Large scale;	84%

: (S)-3-(4-(5-bromo-2-aminobenzyl)phenoxy)tetrahydrofuran

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Stage #1: (S)-3-(4-(5-bromo-2-aminobenzyl)phenoxy)tetrahydrofuran With hydrogenchloride; sodium nitrite In water at -10 - 0℃; for 3h; Large scale; Stage #2: With hydrogenchloride; copper(l) chloride In water at 20 - 80℃; for 3h; Large scale;	74%

: 864070-18-8
4-(5-bromo-2-chlorobenzyl)phenol

: 86087-24-3
(R)-3-Hydroxytetrahydrofuran

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Stage #1: (R)-3-Hydroxytetrahydrofuran With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.5h; Stage #2: 4-(5-bromo-2-chlorobenzyl)phenol In dichloromethane at 20℃; for 20h;	55%

: 21739-92-4
5-bromo-2-chlorobenzoic acid

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / fluorobenzene / 2 h / 15 - 25 °C 2: aluminum (III) chloride / 1 h / 0 - 25 °C 3: potassium tert-butylate / tetrahydrofuran / 0.5 h / 7 - 10 °C 4: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 0 - 23 °C View Scheme
Multi-step reaction with 3 steps 1: polyphosphoric acid / 50 - 85 °C 2: potassium iodide; potassium carbonate / acetonitrile / 50 - 55 °C 3: potassium borohydride; aluminium trichloride / tetrahydrofuran / 0.5 h / 0 - 20 °C View Scheme
Multi-step reaction with 4 steps 1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 2 h / 10 - 20 °C 2: aluminum (III) chloride / dichloromethane / 5 h / 0 - 20 °C 3: potassium tert-butylate / tetrahydrofuran / 2 h / 0 - 10 °C 4: aluminum (III) chloride; potassium borohydride / tetrahydrofuran / 6 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / Reflux 2: aluminum (III) chloride / dichloromethane / 8 h / 0 - 10 °C 3: 18-crown-6 ether; sodium hydroxide / toluene; water / 8 h / 50 - 60 °C 4: hydrogen; aluminum (III) chloride / toluene / 3 h / 20 - 25 °C View Scheme
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 0 - 25 °C 1.2: 25 °C 2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 7 - 10 °C 3.1: 1,1,3,3-Tetramethyldisiloxane; aluminum (III) chloride / toluene / 0 - 23 °C View Scheme

: 21900-52-7
5-bromo-2-chloro-benzoyl chloride

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: aluminum (III) chloride / 1 h / 0 - 25 °C 2: potassium tert-butylate / tetrahydrofuran / 0.5 h / 7 - 10 °C 3: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 0 - 23 °C View Scheme
Multi-step reaction with 3 steps 1: aluminum (III) chloride / dichloromethane / 5 h / 0 - 20 °C 2: potassium tert-butylate / tetrahydrofuran / 2 h / 0 - 10 °C 3: aluminum (III) chloride; potassium borohydride / tetrahydrofuran / 6 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: aluminum (III) chloride / dichloromethane / 8 h / 0 - 10 °C 2: 18-crown-6 ether; sodium hydroxide / toluene; water / 8 h / 50 - 60 °C 3: hydrogen; aluminum (III) chloride / toluene / 3 h / 20 - 25 °C View Scheme

: 915095-85-1
(2-chloro-5-bromophenyl)(4-fluorophenyl)methanone

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 7 - 10 °C 2: aluminum (III) chloride; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 0 - 23 °C View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 100 - 110 °C 2: aluminum (III) chloride; sodium tetrahydroborate / tetrahydrofuran / 24.5 h / 0 - 60 °C View Scheme
Multi-step reaction with 2 steps 1: potassium tert-butylate / tetrahydrofuran / 2 h / 0 - 10 °C 2: aluminum (III) chloride; potassium borohydride / tetrahydrofuran / 6 h / 20 °C View Scheme

: 108-95-2
phenol

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: polyphosphoric acid / 50 - 85 °C 2: potassium iodide; potassium carbonate / acetonitrile / 50 - 55 °C 3: potassium borohydride; aluminium trichloride / tetrahydrofuran / 0.5 h / 0 - 20 °C View Scheme

: 1360568-68-8
(5-bromo-2-chlorophenyl)(4-hydroxyphenyl)methanone

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium iodide; potassium carbonate / acetonitrile / 50 - 55 °C 2: potassium borohydride; aluminium trichloride / tetrahydrofuran / 0.5 h / 0 - 20 °C View Scheme

: (3S)-3-[p-(chloromethyl)phenoxy]tetrahydrofuran

: 106-40-1
4-bromo-aniline

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: zinc(II) chloride / ethyl acetate / 8 h / Reflux; Large scale 2.1: hydrogenchloride; sodium nitrite / water / 3 h / -10 - 0 °C / Large scale 2.2: 3 h / 20 - 80 °C / Large scale View Scheme

: (S)-3-p-cresyltetrahydrofuran

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-chloro-succinimide; dibenzoyl peroxide / Petroleum ether / 6 h / Reflux; Large scale 2.1: zinc(II) chloride / ethyl acetate / 8 h / Reflux; Large scale 3.1: hydrogenchloride; sodium nitrite / water / 3 h / -10 - 0 °C / Large scale 3.2: 3 h / 20 - 80 °C / Large scale View Scheme

: 352-32-9
p-fluorotoluene

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 - 10 °C / Inert atmosphere; Large scale 2.1: N-chloro-succinimide; dibenzoyl peroxide / Petroleum ether / 6 h / Reflux; Large scale 3.1: zinc(II) chloride / ethyl acetate / 8 h / Reflux; Large scale 4.1: hydrogenchloride; sodium nitrite / water / 3 h / -10 - 0 °C / Large scale 4.2: 3 h / 20 - 80 °C / Large scale View Scheme
Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 6 h / 70 °C / Large scale 2.1: ethyl acetate / 0.5 h / Cooling with ice; Large scale 2.2: 6.5 h / 20 - 75 °C / Cooling with ice; Large scale 3.1: hydrogenchloride / water; ethanol / 8 h / Reflux; Large scale 4.1: hydrogenchloride; sodium nitrite / water / 2 h / -5 - 0 °C / Large scale 4.2: 3 h / 60 °C / Large scale 5.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere; Large scale View Scheme

Yield

Multi-step reaction with 4 steps
1.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 - 10 °C / Inert atmosphere; Large scale
2.1: N-chloro-succinimide; dibenzoyl peroxide / Petroleum ether / 6 h / Reflux; Large scale
3.1: zinc(II) chloride / ethyl acetate / 8 h / Reflux; Large scale
4.1: hydrogenchloride; sodium nitrite / water / 3 h / -10 - 0 °C / Large scale
4.2: 3 h / 20 - 80 °C / Large scale
View Scheme

Multi-step reaction with 5 steps
1.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 6 h / 70 °C / Large scale
2.1: ethyl acetate / 0.5 h / Cooling with ice; Large scale
2.2: 6.5 h / 20 - 75 °C / Cooling with ice; Large scale
3.1: hydrogenchloride / water; ethanol / 8 h / Reflux; Large scale
4.1: hydrogenchloride; sodium nitrite / water / 2 h / -5 - 0 °C / Large scale
4.2: 3 h / 60 °C / Large scale
5.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere; Large scale
View Scheme

: 106-40-1
4-bromo-aniline

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: water; methanol / 3.5 h / 20 °C / Cooling with ice; Large scale 2.1: ethyl acetate / 0.5 h / Cooling with ice; Large scale 2.2: 6.5 h / 20 - 75 °C / Cooling with ice; Large scale 3.1: hydrogenchloride / water; ethanol / 8 h / Reflux; Large scale 4.1: hydrogenchloride; sodium nitrite / water / 2 h / -5 - 0 °C / Large scale 4.2: 3 h / 60 °C / Large scale 5.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere; Large scale View Scheme

Yield

Multi-step reaction with 5 steps
1.1: water; methanol / 3.5 h / 20 °C / Cooling with ice; Large scale
2.1: ethyl acetate / 0.5 h / Cooling with ice; Large scale
2.2: 6.5 h / 20 - 75 °C / Cooling with ice; Large scale
3.1: hydrogenchloride / water; ethanol / 8 h / Reflux; Large scale
4.1: hydrogenchloride; sodium nitrite / water / 2 h / -5 - 0 °C / Large scale
4.2: 3 h / 60 °C / Large scale
5.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere; Large scale
View Scheme

: 103-88-8
4-bromoacetanilide

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: ethyl acetate / 0.5 h / Cooling with ice; Large scale 1.2: 6.5 h / 20 - 75 °C / Cooling with ice; Large scale 2.1: hydrogenchloride / water; ethanol / 8 h / Reflux; Large scale 3.1: hydrogenchloride; sodium nitrite / water / 2 h / -5 - 0 °C / Large scale 3.2: 3 h / 60 °C / Large scale 4.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere; Large scale View Scheme

Yield

Multi-step reaction with 4 steps
1.1: ethyl acetate / 0.5 h / Cooling with ice; Large scale
1.2: 6.5 h / 20 - 75 °C / Cooling with ice; Large scale
2.1: hydrogenchloride / water; ethanol / 8 h / Reflux; Large scale
3.1: hydrogenchloride; sodium nitrite / water / 2 h / -5 - 0 °C / Large scale
3.2: 3 h / 60 °C / Large scale
4.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere; Large scale
View Scheme

: 459-46-1
4-Fluorobenzyl bromide

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: ethyl acetate / 0.5 h / Cooling with ice; Large scale 1.2: 6.5 h / 20 - 75 °C / Cooling with ice; Large scale 2.1: hydrogenchloride / water; ethanol / 8 h / Reflux; Large scale 3.1: hydrogenchloride; sodium nitrite / water / 2 h / -5 - 0 °C / Large scale 3.2: 3 h / 60 °C / Large scale 4.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere; Large scale View Scheme

Yield

: N-[4-bromo-2-(4-fluorobenzyl)]acetanilide

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogenchloride / water; ethanol / 8 h / Reflux; Large scale 2.1: hydrogenchloride; sodium nitrite / water / 2 h / -5 - 0 °C / Large scale 2.2: 3 h / 60 °C / Large scale 3.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere; Large scale View Scheme

: 4-bromo-2-(4-fluorobenzyl)aniline

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite / water / 2 h / -5 - 0 °C / Large scale 1.2: 3 h / 60 °C / Large scale 2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere; Large scale View Scheme

: 95-53-4
o-toluidine

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide / dichloromethane / 10 h / 5 °C / Cooling with ice; Large scale 2.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale 2.2: 3 h / 60 °C / Large scale 3.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 4 h / 70 °C / Large scale 4.1: aluminum (III) chloride / ethyl acetate / 9 h / 78 °C / Cooling with ice; Large scale View Scheme

Yield

Multi-step reaction with 4 steps
1.1: N-Bromosuccinimide / dichloromethane / 10 h / 5 °C / Cooling with ice; Large scale
2.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale
2.2: 3 h / 60 °C / Large scale
3.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 4 h / 70 °C / Large scale
4.1: aluminum (III) chloride / ethyl acetate / 9 h / 78 °C / Cooling with ice; Large scale
View Scheme

: 583-75-5
4-Bromo-2-methylaniline

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogenchloride; sodium nitrite / water / 3 h / -5 - 0 °C / Large scale 1.2: 3 h / 60 °C / Large scale 2.1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 4 h / 70 °C / Large scale 3.1: aluminum (III) chloride / ethyl acetate / 9 h / 78 °C / Cooling with ice; Large scale View Scheme

: 54932-72-8
2-chloro-5-bromotoluene

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N-Bromosuccinimide; dibenzoyl peroxide / chloroform / 4 h / 70 °C / Large scale 2: aluminum (III) chloride / ethyl acetate / 9 h / 78 °C / Cooling with ice; Large scale View Scheme

: 462-06-6
fluorobenzene

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium tert-butylate / tetrahydrofuran; tert-butyl alcohol / 1.5 h / 0 - 10 °C / Inert atmosphere; Large scale 2: aluminum (III) chloride / ethyl acetate / 9 h / 78 °C / Cooling with ice; Large scale View Scheme
Multi-step reaction with 2 steps 1.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 10 °C / Inert atmosphere; Large scale 2.1: ethyl acetate / 0.5 h / Cooling with ice; Large scale 2.2: 8.5 h / 78 °C / Cooling with ice; Large scale View Scheme
Multi-step reaction with 3 steps 1.1: N,N-dimethyl-formamide; oxalyl dichloride / 0 - 25 °C 1.2: 25 °C 2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 7 - 10 °C 3.1: 1,1,3,3-Tetramethyldisiloxane; aluminum (III) chloride / toluene / 0 - 23 °C View Scheme

: 189628-37-3
2-chloro-5-bromobenzaldehyde

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate / ethanol / 4 h / 20 °C / Large scale 1.2: pH 4-5 / Cooling with ice; Large scale 2.1: thionyl chloride / 3 h / 70 °C / Large scale 3.1: ethyl acetate / 0.5 h / Cooling with ice; Large scale 3.2: 8.5 h / 78 °C / Cooling with ice; Large scale View Scheme

: 89-98-5
2-chloro-benzaldehyde

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide / dichloromethane / 10 h / 5 °C / Large scale 2.1: sodium tetrahydroborate / ethanol / 4 h / 20 °C / Large scale 2.2: pH 4-5 / Cooling with ice; Large scale 3.1: thionyl chloride / 3 h / 70 °C / Large scale 4.1: ethyl acetate / 0.5 h / Cooling with ice; Large scale 4.2: 8.5 h / 78 °C / Cooling with ice; Large scale View Scheme

: 149965-40-2
5-bromo-2-chlorobenzyl alcohol

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: thionyl chloride / 3 h / 70 °C / Large scale 2.1: ethyl acetate / 0.5 h / Cooling with ice; Large scale 2.2: 8.5 h / 78 °C / Cooling with ice; Large scale View Scheme

: 572-09-8, 3068-32-4, 4026-32-8, 6919-96-6, 13242-53-0, 14227-54-4, 14795-18-7, 19186-59-5, 19285-38-2, 21698-13-5, 29907-26-4, 53369-42-9, 60619-58-1, 61303-35-3, 67337-79-5, 69127-37-3, 70749-15-4, 72002-90-5, 75247-30-2, 75880-74-9, 78418-57-2, 102339-89-9, 102339-90-2, 103530-40-1, 114028-03-4, 114718-45-5, 138514-70-2, 138514-71-3
2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

: (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-trityl triacetate

Conditions

Conditions	Yield
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene With n-butyllithium; isopropyl magnesium chloride - lithium chloride complex In tetrahydrofuran; hexane at -10℃; for 2h; Inert atmosphere; Stage #2: 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide In tetrahydrofuran; hexane at -10℃; for 3h; Inert atmosphere; Stage #3: With methanesulfonic acid In tetrahydrofuran; methanol; hexane at 25℃; for 18h; Reagent/catalyst; Inert atmosphere;	92.6%

Yield

Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene With n-butyllithium; isopropyl magnesium chloride - lithium chloride complex In tetrahydrofuran; hexane at -10℃; for 2h; Inert atmosphere;
Stage #2: 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide In tetrahydrofuran; hexane at -10℃; for 3h; Inert atmosphere;
Stage #3: With methanesulfonic acid In tetrahydrofuran; methanol; hexane at 25℃; for 18h; Reagent/catalyst; Inert atmosphere;

92.6%

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

: 1103738-19-7
((3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(morpholin-4-yl)methanone

: (4-chloro-3-(4-(3(S)-tetrahydrofuranyloxy)benzyl)phenyl)((3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolan-5-yl)methanone

Conditions

Conditions	Yield
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene With n-butyllithium In tetrahydrofuran at -80 - -70℃; for 1h; Stage #2: ((3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(morpholin-4-yl)methanone In tetrahydrofuran at -80 - 0℃;	88.4%

: 67-56-1
methanol

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

: 32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

: 1279691-36-9
(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions

Conditions	Yield
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 1h; Inert atmosphere; Large scale; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -78℃; for 3h; Large scale; Stage #3: methanol With methanesulfonic acid In tetrahydrofuran; hexane; toluene at 0 - 40℃; for 10h; Large scale;	87%
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene; (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 3h; Inert atmosphere; Large scale; Stage #2: methanol With methanesulfonic acid In tetrahydrofuran; hexane; toluene at 0 - 40℃; for 10h; Inert atmosphere; Large scale;	84%

Yield

Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 1h; Inert atmosphere; Large scale;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane; toluene at -78℃; for 3h; Large scale;
Stage #3: methanol With methanesulfonic acid In tetrahydrofuran; hexane; toluene at 0 - 40℃; for 10h; Large scale;

87%

Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene; (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With n-butyllithium In tetrahydrofuran; hexane; toluene at -78℃; for 3h; Inert atmosphere; Large scale;
Stage #2: methanol With methanesulfonic acid In tetrahydrofuran; hexane; toluene at 0 - 40℃; for 10h; Inert atmosphere; Large scale;

84%

...Expand

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

: 32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

: 1279691-36-9
(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Conditions

Conditions	Yield
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene With n-butyllithium In tetrahydrofuran; toluene at -78℃; for 1h; Large scale; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; toluene at -78℃; for 3h; Large scale; Stage #3: With methanesulfonic acid In tetrahydrofuran; methanol; toluene at 0 - 40℃; for 10h; Large scale;	84%

Yield

Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene With n-butyllithium In tetrahydrofuran; toluene at -78℃; for 1h; Large scale;
Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; toluene at -78℃; for 3h; Large scale;
Stage #3: With methanesulfonic acid In tetrahydrofuran; methanol; toluene at 0 - 40℃; for 10h; Large scale;

84%

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

: C18H42O6Si4

: C23H27ClO8

Conditions

Conditions	Yield
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene With n-butyllithium In tetrahydrofuran; hexane at -60 - -50℃; for 0.833333h; Inert atmosphere; Stage #2: C18H42O6Si4 In tetrahydrofuran; hexane at -50℃; Inert atmosphere; Stage #3: With hydrogenchloride In isopropyl alcohol at 0 - 20℃;	80%

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

: 73183-34-3
bis(pinacol)diborane

: 2-[4-chloro-3-({4-[(3S)-oxolan-3-yloxy]phenyl}methyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 8℃; for 8h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere;	71.3%

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

: 81058-27-7
2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide

: C43H59ClO11

Conditions

Conditions	Yield
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene With TurboGrignard In tetrahydrofuran at -10 - 0℃; Cooling with ice; Inert atmosphere; Stage #2: With n-butyllithium In tetrahydrofuran Stage #3: 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide With iron(III)-acetylacetonate In tetrahydrofuran at 40 - 50℃; Inert atmosphere;	67%

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-trityl triacetate

Conditions

Conditions	Yield
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene With TurboGrignard In tetrahydrofuran at -10 - 0℃; for 0.5h; Cooling with ice; Inert atmosphere; Stage #2: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide With iron(III)-acetylacetonate In tetrahydrofuran at 40 - 50℃; Inert atmosphere;	65%

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

: 108-24-7
acetic anhydride

: 32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

: C31H35ClO11

Conditions

Conditions	Yield
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene; (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one With n-butyllithium In tetrahydrofuran; hexane at -95 - -90℃; for 0.5h; Stage #2: With methanesulfonic acid In methanol at 20℃; Stage #3: acetic anhydride Further stages;	58%

...Expand

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

: 32469-28-6, 55515-28-1, 55515-29-2, 32384-65-9
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

: C35H59ClO7Si4

Conditions

Conditions	Yield
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane at -23 - -5℃; for 0.666667h; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -20 - -12℃; for 2h; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water Product distribution / selectivity;
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene With n-butyllithium; isopropylmagnesium chloride; lithium chloride In tetrahydrofuran; hexane at -23 - -5℃; for 0.666667h; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -20 - -12℃; for 2h; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water Product distribution / selectivity;
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene With n-butyllithium; isopropylmagnesium chloride In tetrahydrofuran; hexane at -23 - -5℃; for 0.666667h; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran; hexane at -20 - -12℃; for 2h; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water Product distribution / selectivity;
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at 0 - 20℃; for 16h; Stage #2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at -23 - -20℃; for 2h; Stage #3: With ammonium chloride In tetrahydrofuran; water Product distribution / selectivity;

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

: [13C6]-(3R,4S,5R,6R)-3,4,5-tris-trimethylsilyloxy-6-(trimethylsilyloxymethyl)tetrahydro-2H-pyran-2-one

: C29(13)C6H59ClO8Si4

Conditions

Conditions	Yield
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: [13C6]-(3R,4S,5R,6R)-3,4,5-tris-trimethylsilyloxy-6-(trimethylsilyloxymethyl)tetrahydro-2H-pyran-2-one In tetrahydrofuran at -78℃; for 1.6h;

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

: 74372-90-0
3,4,6-tri-O-benzyl-D-glucal epoxide

: (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

Conditions

Conditions	Yield
Stage #1: (S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene With tri-n-butyllithium magnesate complex In tetrahydrofuran; diethyl ether; hexane at 0℃; for 0.333333h; Inert atmosphere; Stage #2: 3,4,6-tri-O-benzyl-D-glucal epoxide With copper(I) cyanide di(lithium chloride) In tetrahydrofuran; diethyl ether; hexane at 0 - 20℃; Inert atmosphere;

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

: 3,4,5-tris(benzyloxy)-6-(4-chloro-3-(4-(((R)-THF-3-yl)oxy)benzyl)phenyl)hexane-1,2,6-triyl triacetate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: magnesium; iodine / tetrahydrofuran / 1 h / 60 °C 1.2: 2 h / 0 - 60 °C 2.1: toluene-4-sulfonic acid / 2 h / 0 - 70 °C View Scheme

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

: (3R,4R,5S)-3,4,5-tris(benzyloxy)-6-(4-chloro-3-(4-(((R)-THF-3-yl)oxy)benzyl)phenyl)hexane-1,2,6-triol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: magnesium; iodine / tetrahydrofuran / 1 h / 60 °C 1.2: 2 h / 0 - 60 °C 2.1: toluene-4-sulfonic acid / 2 h / 0 - 70 °C 3.1: potassium carbonate / methanol; water / 2 h / 0 - 20 °C View Scheme

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

: (2S,3R,4R)-2,3,4-tris(benzyloxy)-6-((tert-butyldimethylsilyl)oxy)-1-(4-chloro-3-(4-(((S)-THF-3-yl)oxy)benzyl)phenyl)hexane-1,5-diol

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: magnesium; iodine / tetrahydrofuran / 1 h / 60 °C 1.2: 2 h / 0 - 60 °C 2.1: toluene-4-sulfonic acid / 2 h / 0 - 70 °C 3.1: potassium carbonate / methanol; water / 2 h / 0 - 20 °C 4.1: 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere View Scheme

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

: (2R,3R,4S)-2,3,4-tris(benzyloxy)-6-((tert-butyldimethylsilyl)oxy)-1-(4-chloro-3-(4-(((S)-THF-3-yl)oxy)benzyl)phenyl)hexane-1,5-dione

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: magnesium; iodine / tetrahydrofuran / 1 h / 60 °C 1.2: 2 h / 0 - 60 °C 2.1: toluene-4-sulfonic acid / 2 h / 0 - 70 °C 3.1: potassium carbonate / methanol; water / 2 h / 0 - 20 °C 4.1: 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere 5.1: trifluoroacetic anhydride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C 5.2: -78 - 20 °C View Scheme

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

: (1S,2S,3S,4R,5S)-2,3,4-tris(benzyloxy)-5-(4-chloro-3-(4-(((S)-THF-3-yl)oxy)benzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octan-1-ol

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: magnesium; iodine / tetrahydrofuran / 1 h / 60 °C 1.2: 2 h / 0 - 60 °C 2.1: toluene-4-sulfonic acid / 2 h / 0 - 70 °C 3.1: potassium carbonate / methanol; water / 2 h / 0 - 20 °C 4.1: 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere 5.1: trifluoroacetic anhydride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C 5.2: -78 - 20 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / -10 - -5 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: magnesium; iodine / tetrahydrofuran / 1 h / 60 °C
1.2: 2 h / 0 - 60 °C
2.1: toluene-4-sulfonic acid / 2 h / 0 - 70 °C
3.1: potassium carbonate / methanol; water / 2 h / 0 - 20 °C
4.1: 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere
5.1: trifluoroacetic anhydride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C
5.2: -78 - 20 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / -10 - -5 °C
View Scheme

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

: (1S,2S,3R,4R,5S)-2,3,4-tris(benzyloxy)-5-(4-chloro-3-(4-(((S)-THF-3-yl)oxy)benzyl)phenyl)-1-methoxy-6,8-dioxabicyclo[3.2.1]octane

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: magnesium; iodine / tetrahydrofuran / 1 h / 60 °C 1.2: 2 h / 0 - 60 °C 2.1: toluene-4-sulfonic acid / 2 h / 0 - 70 °C 3.1: potassium carbonate / methanol; water / 2 h / 0 - 20 °C 4.1: 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere 5.1: trifluoroacetic anhydride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C 5.2: -78 - 20 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / -10 - -5 °C 7.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 7 steps
1.1: magnesium; iodine / tetrahydrofuran / 1 h / 60 °C
1.2: 2 h / 0 - 60 °C
2.1: toluene-4-sulfonic acid / 2 h / 0 - 70 °C
3.1: potassium carbonate / methanol; water / 2 h / 0 - 20 °C
4.1: 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere
5.1: trifluoroacetic anhydride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C
5.2: -78 - 20 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / -10 - -5 °C
7.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere
View Scheme

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

: (1R,2S,3R,4R,5S)-2,3,4-tris(benzyloxy)-5-(4-chloro-3-(4-(((S)-THF-3-yl)oxy)benzyl)phenyl)-1-(difluoromethoxy)-6,8-dioxabicyclo[3.2.1]octane

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: magnesium; iodine / tetrahydrofuran / 1 h / 60 °C 1.2: 2 h / 0 - 60 °C 2.1: toluene-4-sulfonic acid / 2 h / 0 - 70 °C 3.1: potassium carbonate / methanol; water / 2 h / 0 - 20 °C 4.1: 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere 5.1: trifluoroacetic anhydride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C 5.2: -78 - 20 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / -10 - -5 °C 7.1: potassium hydroxide / water; acetonitrile / 3 h / -5 - 20 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: magnesium; iodine / tetrahydrofuran / 1 h / 60 °C
1.2: 2 h / 0 - 60 °C
2.1: toluene-4-sulfonic acid / 2 h / 0 - 70 °C
3.1: potassium carbonate / methanol; water / 2 h / 0 - 20 °C
4.1: 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere
5.1: trifluoroacetic anhydride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C
5.2: -78 - 20 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / -10 - -5 °C
7.1: potassium hydroxide / water; acetonitrile / 3 h / -5 - 20 °C
View Scheme

: 915095-89-5
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

: (1S,2S,3R,4R,5S)-5-(4-chloro-3-(4-(((S)-THF-3-yl)oxy)benzyl)-phenyl)-1-methoxy-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: magnesium; iodine / tetrahydrofuran / 1 h / 60 °C 1.2: 2 h / 0 - 60 °C 2.1: toluene-4-sulfonic acid / 2 h / 0 - 70 °C 3.1: potassium carbonate / methanol; water / 2 h / 0 - 20 °C 4.1: 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere 5.1: trifluoroacetic anhydride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C 5.2: -78 - 20 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / -10 - -5 °C 7.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere 8.1: hydrogen; 1,2-dichloro-benzene; palladium 10% on activated carbon / methanol; tetrahydrofuran / 16 h / 20 °C View Scheme

Yield

Multi-step reaction with 8 steps
1.1: magnesium; iodine / tetrahydrofuran / 1 h / 60 °C
1.2: 2 h / 0 - 60 °C
2.1: toluene-4-sulfonic acid / 2 h / 0 - 70 °C
3.1: potassium carbonate / methanol; water / 2 h / 0 - 20 °C
4.1: 1H-imidazole / dichloromethane / 20 °C / Inert atmosphere
5.1: trifluoroacetic anhydride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C
5.2: -78 - 20 °C
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / -10 - -5 °C
7.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere
8.1: hydrogen; 1,2-dichloro-benzene; palladium 10% on activated carbon / methanol; tetrahydrofuran / 16 h / 20 °C
View Scheme

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