4-[(2R)-2-(Chloromethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)benzene supplier

: 172900-70-8
(R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutanol

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
With tetrachloromethane; TOP at 20℃; for 16h; trioctylphosphine was added at 10 °ree;C;	82%
With pyridine; thionyl chloride	70%
With N,N-dimethyl-formamide; trichlorophosphate In toluene at 80℃;

: 943349-14-2
2-(3-(3-methoxypropoxy)-4-methoxybenzyl)-3-methylbutanol

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide In toluene at 90℃; for 2h; Product distribution / selectivity;	64%

: 172900-75-3
4-methoxy-3-(3-methoxypropoxy)benzaldehyde

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: 82 percent 2.1: H2 / Pd/C / ethyl acetate / 20 °C 3.1: (COCl)2 / dimethylformamide / 20 °C 4.1: NaOH / toluene / 20 °C 5.1: LDA; LiCl / tetrahydrofuran / 0 °C 5.2: tetrahydrofuran / 20 °C / Heating 6.1: 66 percent / BH3*NH3; n-BuLi / tetrahydrofuran / 20 °C 7.1: POCl3; DMF / toluene / 80 °C View Scheme
Multi-step reaction with 6 steps 1.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 30 °C 1.2: pH 2 2.1: phosphorus tribromide / dichloromethane / 2.17 h / 0 - 5 °C 3.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 3.2: -70 - 5 °C 4.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C 5.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 5.2: 5.75 h / 0 - 30 °C 6.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme
Multi-step reaction with 4 steps 1.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 1 h / 0 - 5 °C / Inert atmosphere 1.2: -30 - -25 °C 1.3: -30 - 5 °C 2.1: hydrogen; acetic acid / palladium on activated charcoal / 60 - 70 °C / 2942.29 Torr 3.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 15 °C 3.2: 11 h / 60 - 65 °C 4.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme

: 3-[4-methoxy-3-(3-methoxy-propoxy)-phenyl]-propionic acid

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: (COCl)2 / dimethylformamide / 20 °C 2.1: NaOH / toluene / 20 °C 3.1: LDA; LiCl / tetrahydrofuran / 0 °C 3.2: tetrahydrofuran / 20 °C / Heating 4.1: 66 percent / BH3*NH3; n-BuLi / tetrahydrofuran / 20 °C 5.1: POCl3; DMF / toluene / 80 °C View Scheme

: 3-[4-methoxy-3-(3-methoxy-propoxy)-phenyl]-propionyl chloride

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: NaOH / toluene / 20 °C 2.1: LDA; LiCl / tetrahydrofuran / 0 °C 2.2: tetrahydrofuran / 20 °C / Heating 3.1: 66 percent / BH3*NH3; n-BuLi / tetrahydrofuran / 20 °C 4.1: POCl3; DMF / toluene / 80 °C View Scheme

: 324763-36-2
(E)-3-[4-Methoxy-3-(3-methoxy-propoxy)-phenyl]-acrylic acid

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: H2 / Pd/C / ethyl acetate / 20 °C 2.1: (COCl)2 / dimethylformamide / 20 °C 3.1: NaOH / toluene / 20 °C 4.1: LDA; LiCl / tetrahydrofuran / 0 °C 4.2: tetrahydrofuran / 20 °C / Heating 5.1: 66 percent / BH3*NH3; n-BuLi / tetrahydrofuran / 20 °C 6.1: POCl3; DMF / toluene / 80 °C View Scheme

: 172900-71-9
(R)-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-(1-methylethyl)propanoic acid

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / NaBH4; I2 / 96 h / 20 °C 2: 70 percent / SOCl2; pyridine View Scheme
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 1.2: 5.75 h / 0 - 30 °C 2.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C 2: thionyl chloride / toluene; N,N-dimethyl acetamide / 2.5 h / 89 - 95 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere; Large scale 1.2: 0 °C / Large scale 2.1: thionyl chloride; sodium hydroxide / toluene; N,N-dimethyl-formamide / 0.5 h / 90 °C / Inert atmosphere; Large scale View Scheme

: 324763-37-3
N-(2-hydroxy-1-methyl-2-phenyl-ethyl)-3-[4-methoxy-3-(3-methoxy-propoxy)-phenyl]-N-methyl-propionamide

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: LDA; LiCl / tetrahydrofuran / 0 °C 1.2: tetrahydrofuran / 20 °C / Heating 2.1: 66 percent / BH3*NH3; n-BuLi / tetrahydrofuran / 20 °C 3.1: POCl3; DMF / toluene / 80 °C View Scheme

: 324763-38-4
N-(2-hydroxy-1-methyl-2-phenyl-ethyl)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3,N-dimethyl-butyramide

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 66 percent / BH3*NH3; n-BuLi / tetrahydrofuran / 20 °C 2: POCl3; DMF / toluene / 80 °C View Scheme

: 503-74-2
3-methylbutyric acid

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: dmap / 1,1-dichloroethane / 0.5 h / 20 °C 1.2: 14.5 h / 10 - 30 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 2.2: -70 - 5 °C 3.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C 4.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 4.2: 5.75 h / 0 - 30 °C 5.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme
Multi-step reaction with 4 steps 1.1: dmap / 1,1-dichloroethane / 0.5 h / 20 °C 1.2: 14.5 h / 10 - 30 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 2.2: -70 - 5 °C 3.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 15 °C 3.2: 11 h / 60 - 65 °C 4.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme
Multi-step reaction with 5 steps 1.1: dmap / 1,1-dichloroethane / 0.5 h / 20 °C 1.2: 14.5 h / 10 - 30 °C 2.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 1 h / 0 - 5 °C / Inert atmosphere 2.2: -30 - -25 °C 2.3: -30 - 5 °C 3.1: hydrogen; acetic acid / palladium on activated charcoal / 60 - 70 °C / 2942.29 Torr 4.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 15 °C 4.2: 11 h / 60 - 65 °C 5.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme
Multi-step reaction with 6 steps 1.1: dmap / 1,1-dichloroethane / 0.5 h / 20 °C 1.2: 14.5 h / 10 - 30 °C 2.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 1 h / 0 - 5 °C / Inert atmosphere 2.2: -30 - -25 °C 2.3: -30 - 5 °C 3.1: hydrogen; acetic acid / palladium on activated charcoal / 60 - 70 °C / 2942.29 Torr 4.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C 5.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 5.2: 5.75 h / 0 - 30 °C 6.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme

: 172900-73-1
4-(bromomethyl)-1-methoxy-2-(3-methoxypropoxy)-benzene

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 1.2: -70 - 5 °C 2.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C 3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 3.2: 5.75 h / 0 - 30 °C 4.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme
Multi-step reaction with 3 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 1.2: -70 - 5 °C 2.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 15 °C 2.2: 11 h / 60 - 65 °C 3.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme
Multi-step reaction with 4 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -10 °C / Inert atmosphere; Large scale 1.2: 20 h / 0 °C / Large scale 2.1: dihydrogen peroxide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Large scale 2.2: Large scale 3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere; Large scale 3.2: 0 °C / Large scale 4.1: thionyl chloride; sodium hydroxide / toluene; N,N-dimethyl-formamide / 0.5 h / 90 °C / Inert atmosphere; Large scale View Scheme

: 172900-74-2
[4-methoxy-3-(3-methoxypropoxy)-phenyl]methanol

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: phosphorus tribromide / dichloromethane / 2.17 h / 0 - 5 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 2.2: -70 - 5 °C 3.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C 4.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 4.2: 5.75 h / 0 - 30 °C 5.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme
Multi-step reaction with 4 steps 1.1: phosphorus tribromide / dichloromethane / 2.17 h / 0 - 5 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 2.2: -70 - 5 °C 3.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 15 °C 3.2: 11 h / 60 - 65 °C 4.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme
Multi-step reaction with 5 steps 1.1: thionyl chloride / dichloromethane / 2 h / 0 °C 2.1: sodium iodide / tetrahydrofuran / 16 h / 25 - 30 °C 3.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 1 h / Cooling with ice; Inert atmosphere 3.2: 16 h / -30 - -5 °C 4.1: sodium tetrahydroborate / tetrahydrofuran; water / 20 °C 5.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 1.5 h / 89 - 95 °C View Scheme
Multi-step reaction with 6 steps 1.1: thionyl chloride / dichloromethane / 3 h / 0 - 5 °C 2.1: sodium iodide / tetrahydrofuran / 16 h / 25 - 30 °C 3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / -78 - -45 °C / Inert atmosphere 3.2: 1 h / -45 - -20 °C 4.1: dihydrogen peroxide; lithium hydrochloride monohydrate; water / tetrahydrofuran / 0 - 25 °C 5.1: sulfuric acid; sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C 6.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 2.5 h / 89 - 95 °C View Scheme
Multi-step reaction with 5 steps 1.1: phosphorus tribromide / dichloromethane / 0 - 5 °C / Inert atmosphere; Large scale 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -10 °C / Inert atmosphere; Large scale 2.2: 20 h / 0 °C / Large scale 3.1: dihydrogen peroxide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Large scale 3.2: Large scale 4.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere; Large scale 4.2: 0 °C / Large scale 5.1: thionyl chloride; sodium hydroxide / toluene; N,N-dimethyl-formamide / 0.5 h / 90 °C / Inert atmosphere; Large scale View Scheme

: (4'R)-3-methyl-1-(2'-oxo-4'-phenyloxazolidin-3'-yl)butan-1-one

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 1.2: -70 - 5 °C 2.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C 3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 3.2: 5.75 h / 0 - 30 °C 4.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme
Multi-step reaction with 3 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -70 °C / Inert atmosphere 1.2: -70 - 5 °C 2.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 15 °C 2.2: 11 h / 60 - 65 °C 3.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme
Multi-step reaction with 4 steps 1.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 1 h / 0 - 5 °C / Inert atmosphere 1.2: -30 - -25 °C 1.3: -30 - 5 °C 2.1: hydrogen; acetic acid / palladium on activated charcoal / 60 - 70 °C / 2942.29 Torr 3.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 15 °C 3.2: 11 h / 60 - 65 °C 4.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme
Multi-step reaction with 5 steps 1.1: titanium(IV) isopropylate; N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / 1 h / 0 - 5 °C / Inert atmosphere 1.2: -30 - -25 °C 1.3: -30 - 5 °C 2.1: hydrogen; acetic acid / palladium on activated charcoal / 60 - 70 °C / 2942.29 Torr 3.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C 4.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 4.2: 5.75 h / 0 - 30 °C 5.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme

: 1350705-31-5
(R)-3-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoyl)-4-phenyloxazolidin-2-one

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C 2.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 2.2: 5.75 h / 0 - 30 °C 3.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 15 °C 1.2: 11 h / 60 - 65 °C 2.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme
Multi-step reaction with 3 steps 1.1: dihydrogen peroxide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Large scale 1.2: Large scale 2.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere; Large scale 2.2: 0 °C / Large scale 3.1: thionyl chloride; sodium hydroxide / toluene; N,N-dimethyl-formamide / 0.5 h / 90 °C / Inert atmosphere; Large scale View Scheme

: 1350705-32-6
(4R)-3-(2S)-(2-(hydroxy(4-methoxy-3-(3-methoxypropoxy)phenyl)methyl)-3-methylbutanoyl)-4-phenyloxazolidin-2-one

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogen; acetic acid / palladium on activated charcoal / 60 - 70 °C / 2942.29 Torr 2.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C 3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere 3.2: 5.75 h / 0 - 30 °C 4.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme
Multi-step reaction with 3 steps 1.1: hydrogen; acetic acid / palladium on activated charcoal / 60 - 70 °C / 2942.29 Torr 2.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 15 °C 2.2: 11 h / 60 - 65 °C 3.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C View Scheme

Yield

Multi-step reaction with 4 steps
1.1: hydrogen; acetic acid / palladium on activated charcoal / 60 - 70 °C / 2942.29 Torr
2.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 30 °C
3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
3.2: 5.75 h / 0 - 30 °C
4.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C
View Scheme

Multi-step reaction with 3 steps
1.1: hydrogen; acetic acid / palladium on activated charcoal / 60 - 70 °C / 2942.29 Torr
2.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 15 °C
2.2: 11 h / 60 - 65 °C
3.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 5.5 h / -40 - 30 °C
View Scheme

: 1381757-32-9
C12H17IO3

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Yield

Multi-step reaction with 3 steps
1.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 1 h / Cooling with ice; Inert atmosphere
1.2: 16 h / -30 - -5 °C
2.1: sodium tetrahydroborate / tetrahydrofuran; water / 20 °C
3.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 1.5 h / 89 - 95 °C
View Scheme

Multi-step reaction with 4 steps
1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / -78 - -45 °C / Inert atmosphere
1.2: 1 h / -45 - -20 °C
2.1: dihydrogen peroxide; lithium hydrochloride monohydrate; water / tetrahydrofuran / 0 - 25 °C
3.1: sulfuric acid; sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C
4.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 2.5 h / 89 - 95 °C
View Scheme

: (2S)-N-<3'-methylbutanoyl>bornane-10,2-sultam

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 1 h / Cooling with ice; Inert atmosphere 1.2: 16 h / -30 - -5 °C 2.1: sodium tetrahydroborate / tetrahydrofuran; water / 20 °C 3.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 1.5 h / 89 - 95 °C View Scheme

: 108-12-3
isopentanoyl chloride

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: dmap; triethylamine / toluene / 0 - 25 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 1 h / Cooling with ice; Inert atmosphere 2.2: 16 h / -30 - -5 °C 3.1: sodium tetrahydroborate / tetrahydrofuran; water / 20 °C 4.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 1.5 h / 89 - 95 °C View Scheme
Multi-step reaction with 5 steps 1.1: sodium hydride / toluene / 4 h / 20 - 25 °C 1.2: 1.5 h / 15 - 30 °C 2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / -78 - -45 °C / Inert atmosphere 2.2: 1 h / -45 - -20 °C 3.1: dihydrogen peroxide; lithium hydrochloride monohydrate; water / tetrahydrofuran / 0 - 25 °C 4.1: sulfuric acid; sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C 5.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 2.5 h / 89 - 95 °C View Scheme
Multi-step reaction with 5 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 15 - 30 °C / Inert atmosphere; Large scale 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -10 °C / Inert atmosphere; Large scale 2.2: 20 h / 0 °C / Large scale 3.1: dihydrogen peroxide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Large scale 3.2: Large scale 4.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere; Large scale 4.2: 0 °C / Large scale 5.1: thionyl chloride; sodium hydroxide / toluene; N,N-dimethyl-formamide / 0.5 h / 90 °C / Inert atmosphere; Large scale View Scheme

: 1179062-77-1
4-chloromethyl-1-methoxy-2-(3-methoxypropoxy)-benzene

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium iodide / tetrahydrofuran / 16 h / 25 - 30 °C 2.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 1 h / Cooling with ice; Inert atmosphere 2.2: 16 h / -30 - -5 °C 3.1: sodium tetrahydroborate / tetrahydrofuran; water / 20 °C 4.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 1.5 h / 89 - 95 °C View Scheme
Multi-step reaction with 5 steps 1.1: sodium iodide / tetrahydrofuran / 16 h / 25 - 30 °C 2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / -78 - -45 °C / Inert atmosphere 2.2: 1 h / -45 - -20 °C 3.1: dihydrogen peroxide; lithium hydrochloride monohydrate; water / tetrahydrofuran / 0 - 25 °C 4.1: sulfuric acid; sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C 5.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 2.5 h / 89 - 95 °C View Scheme

Yield

Multi-step reaction with 4 steps
1.1: sodium iodide / tetrahydrofuran / 16 h / 25 - 30 °C
2.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 1 h / Cooling with ice; Inert atmosphere
2.2: 16 h / -30 - -5 °C
3.1: sodium tetrahydroborate / tetrahydrofuran; water / 20 °C
4.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 1.5 h / 89 - 95 °C
View Scheme

Multi-step reaction with 5 steps
1.1: sodium iodide / tetrahydrofuran / 16 h / 25 - 30 °C
2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / -78 - -45 °C / Inert atmosphere
2.2: 1 h / -45 - -20 °C
3.1: dihydrogen peroxide; lithium hydrochloride monohydrate; water / tetrahydrofuran / 0 - 25 °C
4.1: sulfuric acid; sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C
5.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 2.5 h / 89 - 95 °C
View Scheme

: 145589-03-3
(R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / -78 - -45 °C / Inert atmosphere 1.2: 1 h / -45 - -20 °C 2.1: dihydrogen peroxide; lithium hydrochloride monohydrate; water / tetrahydrofuran / 0 - 25 °C 3.1: sulfuric acid; sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C 4.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 2.5 h / 89 - 95 °C View Scheme

Yield

Multi-step reaction with 4 steps
1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / -78 - -45 °C / Inert atmosphere
1.2: 1 h / -45 - -20 °C
2.1: dihydrogen peroxide; lithium hydrochloride monohydrate; water / tetrahydrofuran / 0 - 25 °C
3.1: sulfuric acid; sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C
4.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 2.5 h / 89 - 95 °C
View Scheme

: 172900-72-0
(4R)-3-{(2R)-2-{[4-methoxy-3-(methoxypropoxy)phenyl]methyl-3-methyl}-1-oxobutyl}-4-(phenylmethyl)oxazolidin-2-one

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: dihydrogen peroxide; lithium hydrochloride monohydrate; water / tetrahydrofuran / 0 - 25 °C 2: sulfuric acid; sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C 3: thionyl chloride / toluene; N,N-dimethyl acetamide / 2.5 h / 89 - 95 °C View Scheme

: 621-59-0
isovanillin

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: potassium carbonate / toluene; dimethyl sulfoxide / 16 h / 25 - 90 °C 2.1: sodium tetrahydroborate / toluene; methanol / 3 h / 0 - 5 °C 3.1: thionyl chloride / dichloromethane / 3 h / 0 - 5 °C 4.1: sodium iodide / tetrahydrofuran / 16 h / 25 - 30 °C 5.1: lithium diisopropyl amide / tetrahydrofuran; hexane / -78 - -45 °C / Inert atmosphere 5.2: 1 h / -45 - -20 °C 6.1: dihydrogen peroxide; lithium hydrochloride monohydrate; water / tetrahydrofuran / 0 - 25 °C 7.1: sulfuric acid; sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C 8.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 2.5 h / 89 - 95 °C View Scheme

Yield

Multi-step reaction with 8 steps
1.1: potassium carbonate / toluene; dimethyl sulfoxide / 16 h / 25 - 90 °C
2.1: sodium tetrahydroborate / toluene; methanol / 3 h / 0 - 5 °C
3.1: thionyl chloride / dichloromethane / 3 h / 0 - 5 °C
4.1: sodium iodide / tetrahydrofuran / 16 h / 25 - 30 °C
5.1: lithium diisopropyl amide / tetrahydrofuran; hexane / -78 - -45 °C / Inert atmosphere
5.2: 1 h / -45 - -20 °C
6.1: dihydrogen peroxide; lithium hydrochloride monohydrate; water / tetrahydrofuran / 0 - 25 °C
7.1: sulfuric acid; sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C
8.1: thionyl chloride / toluene; N,N-dimethyl acetamide / 2.5 h / 89 - 95 °C
View Scheme

: C14H17NO3

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -10 °C / Inert atmosphere; Large scale 1.2: 20 h / 0 °C / Large scale 2.1: dihydrogen peroxide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Large scale 2.2: Large scale 3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere; Large scale 3.2: 0 °C / Large scale 4.1: thionyl chloride; sodium hydroxide / toluene; N,N-dimethyl-formamide / 0.5 h / 90 °C / Inert atmosphere; Large scale View Scheme

Yield

Multi-step reaction with 4 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -10 °C / Inert atmosphere; Large scale
1.2: 20 h / 0 °C / Large scale
2.1: dihydrogen peroxide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Large scale
2.2: Large scale
3.1: sodium tetrahydroborate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere; Large scale
3.2: 0 °C / Large scale
4.1: thionyl chloride; sodium hydroxide / toluene; N,N-dimethyl-formamide / 0.5 h / 90 °C / Inert atmosphere; Large scale
View Scheme

: C10H18ClNO

: 106-93-4
ethylene dibromide

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: C27H45NO4

Conditions

Conditions	Yield
Stage #1: ethylene dibromide With magnesium In tetrahydrofuran at 60℃; Mg was added over a period of 2 min; Stage #2: ethylene dibromide; (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane In tetrahydrofuran for 0.5h; Adding at 62-64 °ree;C; Heating / reflux; Stage #3: C10H18ClNO; 1-methyl-pyrrolidin-2-one; iron-(III)-acetylacetonate In tetrahydrofuran at 0 - 10℃; for 0.25h; Adding at -5-0 °ree;C;	81%

Yield

Stage #1: ethylene dibromide With magnesium In tetrahydrofuran at 60℃; Mg was added over a period of 2 min;
Stage #2: ethylene dibromide; (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane In tetrahydrofuran for 0.5h; Adding at 62-64 °ree;C; Heating / reflux;
Stage #3: C10H18ClNO; 1-methyl-pyrrolidin-2-one; iron-(III)-acetylacetonate In tetrahydrofuran at 0 - 10℃; for 0.25h; Adding at -5-0 °ree;C;

81%

...Expand

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: 900811-38-3
(R)-4-(2-(iodomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

Conditions

Conditions	Yield
With sodium iodide In acetone at 20 - 56℃; for 240h;	80.5%

: 324519-68-8
(2S,4E)-5-chloro-2-isopropyl-N,N-dimethylpent-4-enamide

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: 325154-26-5
(2S,7R,E)-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-N,N,8-trimethylnon-4-enamide

Conditions

Conditions	Yield
Stage #1: (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane With magnesium; ethylene dibromide In 2-methyltetrahydrofuran at 60 - 65℃; Stage #2: (2S,4E)-5-chloro-2-isopropyl-N,N-dimethylpent-4-enamide; iron(III)-acetylacetonate In 2-methyltetrahydrofuran; 1-methyl-pyrrolidin-2-one at 10℃; for 0.25h; Product distribution / selectivity;	80%
Stage #1: (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane With magnesium; ethylene dibromide In tetrahydrofuran at 63 - 68℃; for 4.16667h; Inert atmosphere; Stage #2: (2S,4E)-5-chloro-2-isopropyl-N,N-dimethylpent-4-enamide; iron(III)-acetylacetonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 0 - 5℃; for 1h;
Stage #1: (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane With iodine; methylmagnesium chloride; magnesium; 1-Bromo-2-chloroethane In tetrahydrofuran at 60℃; Reflux; Stage #2: (2S,4E)-5-chloro-2-isopropyl-N,N-dimethylpent-4-enamide With 1-methyl-pyrrolidin-2-one; iron(III)-acetylacetonate In tetrahydrofuran at 0 - 30℃; for 2h;	120 g
Stage #1: (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane With methylmagnesium chloride; magnesium; ethylene dibromide In tetrahydrofuran at 60 - 65℃; Inert atmosphere; Industrial scale; Stage #2: (2S,4E)-5-chloro-2-isopropyl-N,N-dimethylpent-4-enamide With iron(III)-acetylacetonate In tetrahydrofuran; 1-methyl-pyrrolidin-2-one at 0 - 5℃; Concentration; Reagent/catalyst; Temperature; Time; Kumada Cross-Coupling; Inert atmosphere; Industrial scale;
Stage #1: (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane With magnesium; ethylene dibromide In tetrahydrofuran at 65℃; Inert atmosphere; Stage #2: (2S,4E)-5-chloro-2-isopropyl-N,N-dimethylpent-4-enamide With 1-Methylpyrrolidine; iron(III)-acetylacetonate In tetrahydrofuran at -5 - 20℃;	6.5 g

: 324763-44-2
(2S,3S,5R,7S,9S)-9-Isopropyl-3,4-dimethyl-2-phenyl-1,6-dioxa-4-aza-spiro[4.4]nonane-7-carbaldehyde

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

A: 324763-45-3
(3S,5S)-5-{(1R,3S)-1-Hydroxy-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-3-isopropyl-dihydro-furan-2-one

B: 325740-67-8
(3S,5S)-dihydro-5-{(1S,3S)-1-hydroxy-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-4-methylpentyl}-3-(1-methylethyl)furan-2(3H)-one

Conditions

Conditions	Yield
Multistep reaction;	A 51% B n/a

...Expand

: 105-53-3
diethyl malonate

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: 1322077-28-0
C24H38O7

Conditions

Conditions	Yield
With sodium ethanolate; sodium iodide In ethanol	37%

: 54848-33-8
(S)-tetrahydro-5-oxo-2-furancarbonyl chloride

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: 325740-63-4
(S)-5-{(S)-3-[4-Methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentanoyl}-dihydro-furan-2-one

Conditions

Conditions	Yield
With magnesium; ethylene dibromide In tetrahydrofuran at 20℃;

: 325740-60-1
tetrahydro-4-isopropyl-5-oxofuran-2-carbonyl chloride

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: 325740-64-5
(3S,5S)-3-Isopropyl-5-{(S)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentanoyl}-dihydro-furan-2-one

Conditions

Conditions	Yield
With magnesium; ethylene dibromide In tetrahydrofuran at 20℃;
Stage #1: (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane With magnesium; iodine In tetrahydrofuran; 1,2-dibromomethane for 5h; Inert atmosphere; Heating; Reflux; Stage #2: tetrahydro-4-isopropyl-5-oxofuran-2-carbonyl chloride In tetrahydrofuran at 22℃; for 0.5h; Cooling with ice/water bath; Stage #3: With water In tetrahydrofuran Cooling with ice;

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: 437656-17-2, 361460-37-9
C25H32N2O3

A: 361460-39-1
N-Benzyl-N-{(1S,3S)-1-((2S,3S,5S,7S,9S)-9-isopropyl-3,4-dimethyl-2-phenyl-1,6-dioxa-4-aza-spiro[4.4]non-7-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-hydroxylamine

B: 361460-38-0
N-Benzyl-N-{(1R,3S)-1-((2S,3S,5S,7S,9S)-9-isopropyl-3,4-dimethyl-2-phenyl-1,6-dioxa-4-aza-spiro[4.4]non-7-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-hydroxylamine

Conditions

Conditions	Yield
Stage #1: (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane With magnesium; ethylene dibromide In tetrahydrofuran at 45℃; for 1h; Stage #2: C25H32N2O3 In tetrahydrofuran at -40℃; for 15h;
Stage #1: (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane With magnesium; ethylene dibromide In tetrahydrofuran at 45℃; for 1h; Stage #2: C25H32N2O3 With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone In tetrahydrofuran at -10℃; for 15h;
Stage #1: (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane With magnesium; iodine; ethylene dibromide In tetrahydrofuran at 75℃; for 2.25h; Stage #2: C25H32N2O3 In tetrahydrofuran at -10℃; for 15h;	A n/a B n/a
Stage #1: (R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane With cerium(III) chloride Stage #2: C25H32N2O3	A n/a B n/a

...Expand

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: 325740-66-7
(S)-5-{(1S,3S)-1-Hydroxy-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-dihydro-furan-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: K-Selectride / tetrahydrofuran / -78 - 0 °C View Scheme

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: 325740-65-6
(S)-5-{(1R,3S)-1-Hydroxy-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-dihydro-furan-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: K-Selectride / tetrahydrofuran / -78 - 0 °C View Scheme

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: 324763-45-3
(3S,5S)-5-{(1R,3S)-1-Hydroxy-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-3-isopropyl-dihydro-furan-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr View Scheme

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: 325740-67-8
(3S,5S)-dihydro-5-{(1S,3S)-1-hydroxy-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-4-methylpentyl}-3-(1-methylethyl)furan-2(3H)-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr View Scheme

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: 325740-70-3
(3S,5S)-5-((1S,3S)-1-azido-3-(4-methoxy-3-(3-methoxypropoxy)benzyl)-4-methylpentyl)-3-isopropyldihydrofuran-2(3H)-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 3: NEt3 / CH2Cl2 4: 85 percent / NaN3; 15-crown-6; DMPU View Scheme
Multi-step reaction with 5 steps 1.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 1.2: 12.5 h / 0 - 5 °C 2.1: water; lithium hydroxide / tetrahydrofuran; methanol / 26 h / 65 - 70 °C 2.2: 0.5 h / 0 - 5 °C 3.1: hydrogenchloride / 1,1-dichloroethane; water / 0 - 5 °C / pH 2.5 3.2: 14.25 h / 0 - 30 °C 4.1: N-Bromosuccinimide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C 5.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C View Scheme
Multi-step reaction with 2 steps 1.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 1.2: 1 h / 0 - 5 °C 1.3: 0.75 h / 0 - 5 °C 2.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C View Scheme

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: 324763-46-4
(3S,5S)-5-{(1S,3S)-1-azido-3-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-4-methylpentyl}-dihydro-3-(1-methylethyl)furan-2(3H)-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 3: NEt3 / CH2Cl2 4: 85 percent / NaN3; 15-crown-6; DMPU View Scheme
Multi-step reaction with 3 steps 1: 51 percent 2: DMAP / CH2Cl2 / 20 °C 3: NaN3; NMP / 60 °C View Scheme
Multi-step reaction with 3 steps 1.1: magnesium; ethylene dibromide / 2-methyltetrahydrofuran / 60 - 65 °C 1.2: 0.25 h / 10 °C 2.1: N-Bromosuccinimide; phosphoric acid / water; tetrahydrofuran / 5 °C 3.1: sodium azide; Aliquat 336 / water / 48 h / 75 - 80 °C View Scheme
Multi-step reaction with 3 steps 1.1: magnesium; ethylene dibromide / tetrahydrofuran / 65 °C / Inert atmosphere 1.2: -5 - 20 °C 2.1: N-Bromosuccinimide; phosphoric acid / tetrahydrofuran; water / 2 h / 0 - 10 °C / Inert atmosphere 3.1: sodium azide / 2,2'-[1,2-ethanediylbis(oxy)]bisethanol / 72 h / 90 °C / Inert atmosphere View Scheme

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: (3S,5S)-5-{(S)-1-[(Z)-Hydroxyimino]-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-3-isopropyl-dihydro-furan-2-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: 89 percent / NaHCO3 3: 74 percent / H2 / Pd/C / methanol View Scheme
Multi-step reaction with 2 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: 81 percent / NH2OH*HCl; NaHCO3 / methanol / 20 °C View Scheme

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: Methanesulfonic acid (1R,3S)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-1-((S)-5-oxo-tetrahydro-furan-2-yl)-pentyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: K-Selectride / tetrahydrofuran / -78 - 0 °C 3: NEt3 / CH2Cl2 View Scheme

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: Methanesulfonic acid (1S,3S)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-1-((S)-5-oxo-tetrahydro-furan-2-yl)-pentyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: K-Selectride / tetrahydrofuran / -78 - 0 °C 3: NEt3 / CH2Cl2 View Scheme

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: 325740-68-9
Methanesulfonic acid (1R,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 3: NEt3 / CH2Cl2 View Scheme

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: 325740-69-0
Methanesulfonic acid (1S,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 3: NEt3 / CH2Cl2 View Scheme

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: 325740-72-5
(3S,5S)-5-{(S)-1-[(Z)-Benzyloxyimino]-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-3-isopropyl-dihydro-furan-2-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: 89 percent / NaHCO3 View Scheme

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: 387353-75-5
4-Bromo-benzenesulfonic acid (1R,3S)-1-((2S,4S)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 51 percent 2: DMAP / CH2Cl2 / 20 °C View Scheme

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: 325154-32-3
(2S,4S,5R,7S)-5-amino-N-(2-carbamoyl-2-methylpropyl)-4-hydroxy-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methyl-2-isopropylnonanamide

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 3: NEt3 / CH2Cl2 4: 85 percent / NaN3; 15-crown-6; DMPU 5: 59 percent / 2-OH-pyridine; NEt3 6: H2; aq. HCl / Pd/C / methanol View Scheme

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: 173334-57-1
(2S,4S,5S,7S)-5-Amino-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 3: NEt3 / CH2Cl2 4: 85 percent / NaN3; 15-crown-6; DMPU 5: 59 percent / 2-OH-pyridine; NEt3 6: H2; aq. HCl / Pd/C / methanol View Scheme
Multi-step reaction with 13 steps 1.1: sodium ethanolate; sodium iodide / ethanol 2.1: potassium acetate / water; dimethyl sulfoxide 3.1: sodium hydroxide 4.1: thionyl chloride 5.1: pyridine / 12 h / 40 °C 6.1: dicyclohexyl(trifluoromethylsulfonyloxy)borane; triethylamine / -78 - 0 °C 7.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 0.25 h 7.2: Acidic aq. solution 8.1: water; lithium hydroxide / 1,4-dioxane / 120 h / 40 °C 9.1: diphenyl phosphoryl azide; triethylamine / toluene / 0.33 h / 20 °C 10.1: diphenyl phosphoryl azide; triethylamine / toluene / 1 h / 65 °C 11.1: 1.5 h / 65 °C 12.1: 2-hydroxypyridin / tert-butyl methyl ether / 65 °C 13.1: 10% palladium on activated charcoal; hydrogen View Scheme
Multi-step reaction with 7 steps 1.1: magnesium; ethylene dibromide / tetrahydrofuran / 4.17 h / 63 - 68 °C / Inert atmosphere 1.2: 12.5 h / 0 - 5 °C 2.1: water; lithium hydroxide / tetrahydrofuran; methanol / 26 h / 65 - 70 °C 2.2: 0.5 h / 0 - 5 °C 3.1: hydrogenchloride / 1,1-dichloroethane; water / 0 - 5 °C / pH 2.5 3.2: 14.25 h / 0 - 30 °C 4.1: N-Bromosuccinimide; phosphoric acid / water; tetrahydrofuran / 1.25 h / 0 - 5 °C 5.1: sodium azide / ethylene glycol / 20 h / 80 - 85 °C 6.1: triethylamine; 2-hydroxypyridin / 16 h / 85 - 90 °C 7.1: hydrogen; ethanolamine / palladium 10% on activated carbon / isopropyl alcohol / 3 h View Scheme

: 324763-39-5
(R)-2-[4-methoxy-3-(3-methoxypropoxyl)]phenylmethyl-3-methyl-1-chlorobutane

: 325154-31-2
(2S,4S,5R,7S)-5-Azido-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-nonanoic acid (2-carbamoyl-2-methyl-propyl)-amide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: Mg; BrCH2CH2Br / tetrahydrofuran / 20 °C 2: H2 / [Ru2Cl4((S)-BINAP)]NEt3 / methanol / 40 h / 40 °C / 37503 Torr 3: NEt3 / CH2Cl2 4: 85 percent / NaN3; 15-crown-6; DMPU 5: 59 percent / 2-OH-pyridine; NEt3 View Scheme

Product Name

Benzene, 4-[(2R)-2-(chloromethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)-

Synthetic route

4-[(2R)-2-(Chloromethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)benzene Chemical Properties

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