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915095-89-5

915095-89-5

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  • 99% up by HPLC Empagliflozin Intermediate/ (3S)-3-[4-[(5-Bromo-2-Chlorophenyl)Methyl]Phenoxy]Tetrahydrofuran/ 915095-89-5

    Cas No: 915095-89-5

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  • High Quality 99% 915095-89-5 (3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydro-furan Manufacturer

    Cas No: 915095-89-5

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915095-89-5 Usage

Description

(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran is used as a reactant to efficiently synthesize SGLT- 2 Epagliflozin inhibitors.

Physical Form

Solid

synthesis

To a mixture of AlCl3 (61.7 g, 0.463 mol) and (S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone (100 g, 0.231 mol) in toluene (450 mL) was added 1,1,3,3-tetramethyldisiloxane (40.4 g, 0.301 mol) over 1 hour at <20 °C. The mixture was held at 20-23 °C for an additional 1.5 hours and cooled to 0-5 °C. The cooled solution was slowly added to ice-water (400 mL) over 15 min and the layers separated. The organic was treated with 3N NaOH (400 mL) at room temperature for 16-24 hours and the layers were separated. The organic was concentrated to a low volume (~130 mL). After diluted with acetonitrile (450 mL), the solution was again concentrated to a low volume (~130 mL). To the residue was added acetonitrile (400 mL) followed by a slow addition of water (200 mL). The resulting mixture was cooled to 0-3 °C and held for 2 hours. The solids were collected by filtration and dried in oven to give product. (S)-3-(4-(2-chloro-5- bromobenzyl)phenoxy)tetrahydrofuran (2a). 92% as white crystals.

Uses

(3S)-3-[4-[(5-Bromo-2-chlorophenyl)methyl]phenoxy]tetrahydrofuran is used as a reactant in the efficient synthesis of empagliflozin inhibitor of SGLT-2 utilizing AlCl3-promoted silane reduction of β-glycopyranoside.

Check Digit Verification of cas no

The CAS Registry Mumber 915095-89-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 9,1,5,0,9 and 5 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 915095-89:
(8*9)+(7*1)+(6*5)+(5*0)+(4*9)+(3*5)+(2*8)+(1*9)=185
185 % 10 = 5
So 915095-89-5 is a valid CAS Registry Number.

915095-89-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name (3S)-3-[4-[(5-bromo-2-chlorophenyl)methyl]phenoxy]oxolane

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:915095-89-5 SDS

915095-89-5Synthetic route

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

(S)-(5-bromo-2-chlorophenyl)(4-((tetrahydrofuran-3-yl)oxy)phenyl)methanone

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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

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

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

(S)-3-hydroxytetyrahydrofurane

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at 0 - 10℃; for 1h; Inert atmosphere; Large scale;88%
4-bromo-1-chloro-2-(chloromethyl)benzene

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

(S)-3-phenoxytetrahydrofuran

(S)-3-phenoxytetrahydrofuran

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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

(S)-3-phenoxytetrahydrofuran

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

5-Bromo-2-chlorobenzyl bromide

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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

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

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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%
4-(5-bromo-2-chlorobenzyl)phenol
864070-18-8

4-(5-bromo-2-chlorobenzyl)phenol

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

(R)-3-Hydroxytetrahydrofuran

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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%
5-bromo-2-chlorobenzoic acid
21739-92-4

5-bromo-2-chlorobenzoic acid

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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
5-bromo-2-chloro-benzoyl chloride
21900-52-7

5-bromo-2-chloro-benzoyl chloride

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

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

(2-chloro-5-bromophenyl)(4-fluorophenyl)methanone

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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
phenol
108-95-2

phenol

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

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

(5-bromo-2-chlorophenyl)(4-hydroxyphenyl)methanone

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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

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

4-bromo-aniline
106-40-1

4-bromo-aniline

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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

(S)-3-p-cresyltetrahydrofuran

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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
p-fluorotoluene
352-32-9

p-fluorotoluene

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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
4-bromo-aniline
106-40-1

4-bromo-aniline

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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
4-bromoacetanilide
103-88-8

4-bromoacetanilide

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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
4-Fluorobenzyl bromide
459-46-1

4-Fluorobenzyl bromide

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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
N-[4-bromo-2-(4-fluorobenzyl)]acetanilide

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

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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

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

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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
o-toluidine
95-53-4

o-toluidine

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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
4-Bromo-2-methylaniline
583-75-5

4-Bromo-2-methylaniline

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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
2-chloro-5-bromotoluene
54932-72-8

2-chloro-5-bromotoluene

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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
fluorobenzene
462-06-6

fluorobenzene

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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
2-chloro-5-bromobenzaldehyde
189628-37-3

2-chloro-5-bromobenzaldehyde

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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
2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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
5-bromo-2-chlorobenzyl alcohol
149965-40-2

5-bromo-2-chlorobenzyl alcohol

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

Conditions
ConditionsYield
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
2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide
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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene
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

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

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

(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
ConditionsYield
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%
methanol
67-56-1

methanol

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

(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
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

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

(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
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

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

C18H42O6Si4

C18H42O6Si4

C23H27ClO8

C23H27ClO8

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

bis(pinacol)diborane
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

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

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

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

2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide

C43H59ClO11

C43H59ClO11

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
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

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

acetic anhydride
108-24-7

acetic anhydride

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one
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

C31H35ClO11

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

(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
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

C35H59ClO7Si4

Conditions
ConditionsYield
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;
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene
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

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

C29(13)C6H59ClO8Si4

C29(13)C6H59ClO8Si4

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

(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene

3,4,6-tri-O-benzyl-D-glucal epoxide
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

(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
ConditionsYield
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;
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene
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

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

Conditions
ConditionsYield
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
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene
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

(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
ConditionsYield
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
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene
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

(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
ConditionsYield
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
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene
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

(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
ConditionsYield
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
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene
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

(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
ConditionsYield
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
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene
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

(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
ConditionsYield
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
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene
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

(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
ConditionsYield
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
(S)-4-bromo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)benzene
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

(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
ConditionsYield
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

915095-89-5Relevant articles and documents

Enantioselective Hydrogenation toward Chiral 3-Aryloxy Tetrahydrofurans Enabled by Spiro Ir-PNN Catalysts Containing an Unusual 5-Substituted Chiral Oxazoline Unit

Gu, Xue-Song,Xie, Jian-Hua,Xiong, Ying,Yan, Pu-Cha,Yang, Fan,Yu, Na,Zhou, Qi-Lin

, p. 2206 - 2211 (2022/02/09)

An iridium-catalyzed asymmetric hydrogenation of racemic α-aryloxy lactones involving dynamic kinetic resolution was successfully implemented by chiral spiro PNN-ligands containing a C5-substituted chiral oxazoline unit. This protocol along with simple dehydration constitutes the most straightforward approach to prepare enantiomerically enriched 3-aryloxy tetrahydrofurans, which are prevalent structural motifs in many approved drugs and clinical candidates. The hydrogenation step features high yields (90-96%), low catalyst loading (0.2-0.1 mol %), and high enantioselectivities (91-96% ee), and the dehydration step is absolutely stereospecific with high yields (up to 96%) under the mild condition. Moreover, the synthetic utility was further proved by the formal enantioselective synthesis of empagliflozin and production of 3-aryloxy pyrrolidine units.

New crystal form of and preparation method thereof

-

Paragraph 0047-0048, (2021/11/21)

More specifically, the invention provides a novel crystal form of (3S) -3 - [(4 -bromo 5 -2 - chlorophenyl) methyl] phenoxy] tetrahydrofuran and a preparation method of the novel crystal form, and the new crystal form has higher melting point. The hygroscopicity is lower. The preparation method is simple in reaction, high in operability, good in product quality and high in yield, and is a preparation process suitable for industrialization.

Synthetic method of empagliflozin

-

, (2020/02/14)

The invention provides a brand-new synthesis process of empagliflozin. According to the process, a boric acid ester is used for halogen removal, and specific reaction conditions are combined, so thatempagliflozin can be prepared with high yield and simplicity and convenience in operation. The synthesis method of empagliflozin has the advantages of mild reaction conditions, high total yield, few side reactions and convenience in operation, thereby being beneficial to industrial production and cost control.

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