Product Name

  • Name

    2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene

  • EINECS
  • CAS No. 172900-69-5
  • Article Data6
  • CAS DataBase
  • Density 1.173 g/cm3
  • Solubility
  • Melting Point 52-53 °C
  • Formula C17H27BrO3
  • Boiling Point 398.8 °C at 760 mmHg
  • Molecular Weight 359.304
  • Flash Point 164.4 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 172900-69-5 (2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene)
  • Hazard Symbols
  • Synonyms Benzene,4-[2-(bromomethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)-, (R)-;
  • PSA 27.69000
  • LogP 4.32010

Synthetic route

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

(R)-2-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutanol

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

Conditions
ConditionsYield
With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 20℃; for 18h;97%
With N-Bromosuccinimide; triphenylphosphine In dichloromethane97%
With phosphorus(V) oxybromide In N,N-dimethyl-formamide at 20℃; for 8h; Temperature; Time; Solvent;79.6%
isovanillin
621-59-0

isovanillin

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 98 percent / K2CO3 / acetonitrile
2: NaBH4 / ethanol
3: PBr3 / CH2Cl2
4: 76 percent / LiHMDS / tetrahydrofuran
5: 81 percent / LiOH; H2O2
6: 95 percent / LAH / tetrahydrofuran
7: 97 percent / PPh3; NBS / CH2Cl2
View Scheme
Multi-step reaction with 8 steps
1.1: 93 percent / K2CO3 / acetonitrile / 19 h / Heating
2.1: 72 percent / NaOMe / methanol / 1.5 h / Heating
3.1: 96 percent / NaBH4 / methanol / 1 h / 20 °C
4.1: 100 percent / Me3SiBr / 0.17 h / 20 °C
5.1: LiHMDS / tetrahydrofuran / 1.25 h / -70 °C
5.2: 86 percent / tetrahydrofuran / 18 h / 0 °C
6.1: 94 percent / H2O2; LiOH / tetrahydrofuran; H2O / 3 h / 20 °C
7.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C
7.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C
8.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / acetonitrile / Reflux
2.1: potassium borohydride / methanol / 20 °C
3.1: phosphorus tribromide / dichloromethane / 2 h / 20 °C
4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.17 h / 70 °C / Inert atmosphere
4.2: 0 - 70 °C / Inert atmosphere
5.1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 0 - 20 °C
6.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere
7.1: phosphorus tribromide / dichloromethane / 0 °C
View Scheme
(R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one
145589-03-3

(R)-4-benzyl-3-(3-methylbutyryl)oxazolidin-2-one

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 76 percent / LiHMDS / tetrahydrofuran
2: 81 percent / LiOH; H2O2
3: 95 percent / LAH / tetrahydrofuran
4: 97 percent / PPh3; NBS / CH2Cl2
View Scheme
Multi-step reaction with 4 steps
1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.17 h / 70 °C / Inert atmosphere
1.2: 0 - 70 °C / Inert atmosphere
2.1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 0 - 20 °C
3.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere
4.1: phosphorus tribromide / dichloromethane / 0 °C
View Scheme
4-methoxy-3-(3-methoxypropoxy)benzaldehyde
172900-75-3

4-methoxy-3-(3-methoxypropoxy)benzaldehyde

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: NaBH4 / ethanol
2: PBr3 / CH2Cl2
3: 76 percent / LiHMDS / tetrahydrofuran
4: 81 percent / LiOH; H2O2
5: 95 percent / LAH / tetrahydrofuran
6: 97 percent / PPh3; NBS / CH2Cl2
View Scheme
Multi-step reaction with 6 steps
1.1: 96 percent / NaBH4 / methanol / 1 h / 20 °C
2.1: 100 percent / Me3SiBr / 0.17 h / 20 °C
3.1: LiHMDS / tetrahydrofuran / 1.25 h / -70 °C
3.2: 86 percent / tetrahydrofuran / 18 h / 0 °C
4.1: 94 percent / H2O2; LiOH / tetrahydrofuran; H2O / 3 h / 20 °C
5.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C
5.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C
6.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °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: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C
View Scheme
(R)-3-[4-methoxy-3-(3-methoxypropoxy)phenyl]-2-(1-methylethyl)propanoic acid
172900-71-9

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

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / LAH / tetrahydrofuran
2: 97 percent / PPh3; NBS / CH2Cl2
View Scheme
Multi-step reaction with 2 steps
1.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C
1.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C
2.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C
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: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere
2: phosphorus tribromide / dichloromethane / 0 °C
View Scheme
4-(bromomethyl)-1-methoxy-2-(3-methoxypropoxy)-benzene
172900-73-1

4-(bromomethyl)-1-methoxy-2-(3-methoxypropoxy)-benzene

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 76 percent / LiHMDS / tetrahydrofuran
2: 81 percent / LiOH; H2O2
3: 95 percent / LAH / tetrahydrofuran
4: 97 percent / PPh3; NBS / CH2Cl2
View Scheme
Multi-step reaction with 4 steps
1.1: LiHMDS / tetrahydrofuran / 1.25 h / -70 °C
1.2: 86 percent / tetrahydrofuran / 18 h / 0 °C
2.1: 94 percent / H2O2; LiOH / tetrahydrofuran; H2O / 3 h / 20 °C
3.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C
3.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C
4.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C
View Scheme
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: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C
View Scheme
[4-methoxy-3-(3-methoxypropoxy)-phenyl]methanol
172900-74-2

[4-methoxy-3-(3-methoxypropoxy)-phenyl]methanol

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: PBr3 / CH2Cl2
2: 76 percent / LiHMDS / tetrahydrofuran
3: 81 percent / LiOH; H2O2
4: 95 percent / LAH / tetrahydrofuran
5: 97 percent / PPh3; NBS / CH2Cl2
View Scheme
Multi-step reaction with 5 steps
1.1: 100 percent / Me3SiBr / 0.17 h / 20 °C
2.1: LiHMDS / tetrahydrofuran / 1.25 h / -70 °C
2.2: 86 percent / tetrahydrofuran / 18 h / 0 °C
3.1: 94 percent / H2O2; LiOH / tetrahydrofuran; H2O / 3 h / 20 °C
4.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C
4.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C
5.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C
View Scheme
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: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C
View Scheme
(4R)-3-{(2R)-2-{[4-methoxy-3-(methoxypropoxy)phenyl]methyl-3-methyl}-1-oxobutyl}-4-(phenylmethyl)oxazolidin-2-one
172900-72-0

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

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 81 percent / LiOH; H2O2
2: 95 percent / LAH / tetrahydrofuran
3: 97 percent / PPh3; NBS / CH2Cl2
View Scheme
Multi-step reaction with 3 steps
1.1: 94 percent / H2O2; LiOH / tetrahydrofuran; H2O / 3 h / 20 °C
2.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C
2.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C
3.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 0 - 20 °C
2: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere
3: phosphorus tribromide / dichloromethane / 0 °C
View Scheme
3-(3-bromopropoxy)-4-methoxybenzaldehyde
148433-01-6

3-(3-bromopropoxy)-4-methoxybenzaldehyde

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 72 percent / NaOMe / methanol / 1.5 h / Heating
2.1: 96 percent / NaBH4 / methanol / 1 h / 20 °C
3.1: 100 percent / Me3SiBr / 0.17 h / 20 °C
4.1: LiHMDS / tetrahydrofuran / 1.25 h / -70 °C
4.2: 86 percent / tetrahydrofuran / 18 h / 0 °C
5.1: 94 percent / H2O2; LiOH / tetrahydrofuran; H2O / 3 h / 20 °C
6.1: NaBH4 / tetrahydrofuran / 0.75 h / 20 °C
6.2: 90 percent / I2 / tetrahydrofuran / 96 h / 20 °C
7.1: 97 percent / NBS; Ph3P / CH2Cl2 / 18 h / 20 °C
View Scheme
3-methylbutyric acid
503-74-2

3-methylbutyric acid

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

Conditions
ConditionsYield
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: triphenylphosphine; N-Bromosuccinimide / 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: triphenylphosphine; N-Bromosuccinimide / 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: triphenylphosphine; N-Bromosuccinimide / 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: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C
View Scheme
(4'R)-3-methyl-1-(2'-oxo-4'-phenyloxazolidin-3'-yl)butan-1-one

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

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

Conditions
ConditionsYield
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: triphenylphosphine; N-Bromosuccinimide / 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: triphenylphosphine; N-Bromosuccinimide / 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: triphenylphosphine; N-Bromosuccinimide / 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: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C
View Scheme
(R)-3-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoyl)-4-phenyloxazolidin-2-one
1350705-31-5

(R)-3-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoyl)-4-phenyloxazolidin-2-one

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

Conditions
ConditionsYield
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: triphenylphosphine; N-Bromosuccinimide / 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: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C
View Scheme
(4R)-3-(2S)-(2-(hydroxy(4-methoxy-3-(3-methoxypropoxy)phenyl)methyl)-3-methylbutanoyl)-4-phenyloxazolidin-2-one
1350705-32-6

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

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

Conditions
ConditionsYield
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: triphenylphosphine; N-Bromosuccinimide / 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: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 5.5 h / -40 - 30 °C
View Scheme
3-hydroxy-4-methoxybenzyl alcohol
4383-06-6

3-hydroxy-4-methoxybenzyl alcohol

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: potassium carbonate / acetonitrile / 10 h / 25 - 35 °C / Reflux
2.1: phosphorus tribromide / dichloromethane / 2 h / 0 - 10 °C
3.1: toluene / 2 h / 85 - 90 °C
4.1: sodium hydroxide; water / ethanol / 72 h / Reflux
4.2: pH 1 - 1.2
4.3: 35 h / 155 °C
5.1: (S)-1-phenyl-ethylamine / ethyl acetate / 4 h / 10 °C
5.2: pH 1 - 1.2
6.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 2 h / 20 °C
6.2: 5 °C
7.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 4 h / 5 - 10 °C
View Scheme
2-isopropyl-3-{2-[3-methoxy(propyloxy)]-4-methoxyphenyl}propionic acid
325154-22-1

2-isopropyl-3-{2-[3-methoxy(propyloxy)]-4-methoxyphenyl}propionic acid

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: (S)-1-phenyl-ethylamine / ethyl acetate / 4 h / 10 °C
1.2: pH 1 - 1.2
2.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 2 h / 20 °C
2.2: 5 °C
3.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 4 h / 5 - 10 °C
View Scheme
dimethyl-2(4-methoxy-3-(3-methoxypropyloxy)-benzyl)-2-isopropyl malonate
1381757-31-8

dimethyl-2(4-methoxy-3-(3-methoxypropyloxy)-benzyl)-2-isopropyl malonate

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydroxide; water / ethanol / 72 h / Reflux
1.2: pH 1 - 1.2
1.3: 35 h / 155 °C
2.1: (S)-1-phenyl-ethylamine / ethyl acetate / 4 h / 10 °C
2.2: pH 1 - 1.2
3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 2 h / 20 °C
3.2: 5 °C
4.1: triphenylphosphine; N-Bromosuccinimide / dichloromethane / 4 h / 5 - 10 °C
View Scheme
isopentanoyl chloride
108-12-3

isopentanoyl chloride

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium hydride / tetrahydrofuran / 0 - 5 °C / Inert atmosphere
2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.17 h / 70 °C / Inert atmosphere
2.2: 0 - 70 °C / Inert atmosphere
3.1: dihydrogen peroxide; lithium hydroxide monohydrate / tetrahydrofuran; water / 0 - 20 °C
4.1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere
5.1: phosphorus tribromide / dichloromethane / 0 °C
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

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

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

Conditions
ConditionsYield
With sodium iodide In acetone at 20℃; for 20h;95%
(2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine
109838-85-9

(2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

(2S,5R)-2,5-dihydro-3,6-dimethoxy-2-{(2S)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-5-(1-methylethyl)pyrazine
656241-17-7

(2S,5R)-2,5-dihydro-3,6-dimethoxy-2-{(2S)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-5-(1-methylethyl)pyrazine

Conditions
ConditionsYield
Stage #1: (2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine With n-butyllithium In hexane at -75℃; for 0.5h;
Stage #2: (R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene In tetrahydrofuran at -75 - -20℃; for 20h;		91%
Stage #1: (2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine With n-butyllithium In tetrahydrofuran at -75℃;
Stage #2: (R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene In tetrahydrofuran at -75 - -18℃;		90%
(S)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine
78342-42-4

(S)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

(2R,5S)-2,5-dihydro-3,6-dimethoxy-2-{(2R)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-5-(1-methylethyl)pyrazine
656241-33-7

(2R,5S)-2,5-dihydro-3,6-dimethoxy-2-{(2R)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-5-(1-methylethyl)pyrazine

Conditions
ConditionsYield
Stage #1: (S)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine With n-butyllithium In hexane at -75℃; for 2h;
Stage #2: (R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene In tetrahydrofuran at -20℃; for 16h;		68%
(2R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine
110117-71-0

(2R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

(2R,5S)-3,6-diethoxy-2-isopropyl-5-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-2,5-dihydropyrazine
866030-33-3

(2R,5S)-3,6-diethoxy-2-isopropyl-5-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-2,5-dihydropyrazine

Conditions
ConditionsYield
With n-butyllithium68%
Stage #1: (2R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine With n-butyllithium In tetrahydrofuran at -78℃; for 0.833333h;
Stage #2: (R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene In tetrahydrofuran for 168h;
(S)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine
78342-42-4

(S)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

A

(2S,5S)-2,5-dihydro-3,6-dimethoxy-2-{(2S)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-5-(1-methylethyl)pyrazine

(2S,5S)-2,5-dihydro-3,6-dimethoxy-2-{(2S)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-5-(1-methylethyl)pyrazine

B

(2R,5S)-2,5-dihydro-3,6-dimethoxy-2-{(2S)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-5-(1-methylethyl)pyrazine
656241-32-6

(2R,5S)-2,5-dihydro-3,6-dimethoxy-2-{(2S)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-5-(1-methylethyl)pyrazine

Conditions
ConditionsYield
Stage #1: (S)-2-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine With n-butyllithium In hexane at -75℃; for 0.5h;
Stage #2: (R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene In tetrahydrofuran at -75 - -20℃; for 50h;		A 26%
B 28%
...Expand
(2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine
109838-85-9

(2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

A

(2S,5R)-2,5-dihydro-3,6-dimethoxy-2-{(2R)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-5-(1-methylethyl)pyrazine

(2S,5R)-2,5-dihydro-3,6-dimethoxy-2-{(2R)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-5-(1-methylethyl)pyrazine

B

(2R,5R)-2-Isopropyl-3,6-dimethoxy-5-{(R)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyl}-2,5-dihydro-pyrazine

(2R,5R)-2-Isopropyl-3,6-dimethoxy-5-{(R)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyl}-2,5-dihydro-pyrazine

Conditions
ConditionsYield
Stage #1: (2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine With n-butyllithium In hexane at -75℃; for 2h;
Stage #2: (R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene In tetrahydrofuran at -20℃; for 16h;		A 20%
B 22%
...Expand
3,6-Diethoxy-2,5-dihydropyridazin
38629-19-5

3,6-Diethoxy-2,5-dihydropyridazin

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

A

(2R)-3,6-diethoxy-2,5-dihydro-2-{(2S)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-pyrazine

(2R)-3,6-diethoxy-2,5-dihydro-2-{(2S)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-pyrazine

B

(2S)-3,6-diethoxy-2,5-dihydro-2-{(2S)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-pyrazine
172900-68-4

(2S)-3,6-diethoxy-2,5-dihydro-2-{(2S)-2-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-3-methylbutyl}-pyrazine

Conditions
ConditionsYield
Stage #1: 3,6-Diethoxy-2,5-dihydropyridazin With n-butyllithium In tetrahydrofuran; hexane at -40℃; for 0.25h;
Stage #2: (R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene In tetrahydrofuran at -20℃; for 16h;
...Expand
sodium cyanide
143-33-9

sodium cyanide

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

(S)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentanenitrile
960124-88-3

(S)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentanenitrile

Conditions
ConditionsYield
In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone at 50℃; for 2h;
In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone at 50℃; for 2h;
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

tert-butyl {(1S,3S)-1-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate
866030-35-5

tert-butyl {(1S,3S)-1-((2S,4S)-4-isopropyl-5-oxotetrahydrofuran-2-yl)-3-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methylpentyl}carbamate

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 39 mg / H2 / Pd/C / ethanol / 48 h
10.1: 63 percent / Et3N / tetrahydrofuran / 18 h / 20 °C
View Scheme
Multi-step reaction with 11 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C
10.1: 94 percent / H2 / Pd/C / ethanol / 18 h
11.1: 63 percent / Et3N / tetrahydrofuran / 18 h / 20 °C
View Scheme
Multi-step reaction with 8 steps
1: 68 percent / n-BuLi
2: HCl / acetonitrile
3: Et3N
4: NaBH4 / ethanol
5: 89 percent / DMSO; ClC(O)C(O)Cl; Et3N / CH2Cl2
6: Mg
7: 23 percent / H2 / Pd(OH)2/C
8: 38 percent / TPAP; NMMO
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

(5S)-dihydro-5-[(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-aminopentyl]-3-(1-methylethyl)-2(3H)-furanone

(5S)-dihydro-5-[(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-aminopentyl]-3-(1-methylethyl)-2(3H)-furanone

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 39 mg / H2 / Pd/C / ethanol / 48 h
View Scheme
Multi-step reaction with 10 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C
10.1: 94 percent / H2 / Pd/C / ethanol / 18 h
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

methyl (2S,4S)-2-[[(phenylmethoxy)carbonyl]amino]-4-methoxy-3-(3-methoxypropoxy)-γ-(1-methylethyl)benzenepentanoate
900811-40-7

methyl (2S,4S)-2-[[(phenylmethoxy)carbonyl]amino]-4-methoxy-3-(3-methoxypropoxy)-γ-(1-methylethyl)benzenepentanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

(S)-3-Isopropyl-5-((1S,3S)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-1-{[1-phenyl-meth-(E)-ylidene]-amino}-pentyl)-dihydro-furan-2-one

(S)-3-Isopropyl-5-((1S,3S)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-1-{[1-phenyl-meth-(E)-ylidene]-amino}-pentyl)-dihydro-furan-2-one

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 39 mg / H2 / Pd/C / ethanol / 48 h
10.1: ethanol / 1.5 h / 0 °C
View Scheme
Multi-step reaction with 11 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C
10.1: 94 percent / H2 / Pd/C / ethanol / 18 h
11.1: ethanol / 1.5 h / 0 °C
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

(2S,4S)-2-[[(phenylmethoxy)carbonyl]amino]-4-methoxy-3-(3-methoxypropoxy)-γ-(1-methylethyl)benzenepentanoic acid
900811-41-8

(2S,4S)-2-[[(phenylmethoxy)carbonyl]amino]-4-methoxy-3-(3-methoxypropoxy)-γ-(1-methylethyl)benzenepentanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

(2S,4S)-2-Amino-4-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-5-methyl-hexanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

(2S,4S)-2-Amino-4-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-5-methyl-hexanoic acid ((1R,2R)-2-hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / NaI / acetone / 20 h / 20 °C
2: LiHMDS; LiCl / tetrahydrofuran / 0 - 20 °C
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

(3R,5S)-dihydro-5-[(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(phenylmethyl)amino]pentyl]-3-(1-methylethyl)-2(3H)-furanone

(3R,5S)-dihydro-5-[(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(phenylmethyl)amino]pentyl]-3-(1-methylethyl)-2(3H)-furanone

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 39 mg / H2 / Pd/C / ethanol / 48 h
10.1: ethanol / 1.5 h / 0 °C
11.1: 6 mg / NaBH4 / ethanol / 0.67 h / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C
10.1: 94 percent / H2 / Pd/C / ethanol / 18 h
11.1: ethanol / 1.5 h / 0 °C
12.1: 6 mg / NaBH4 / ethanol / 0.67 h / 20 °C
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

(3S,5S)-dihydro-5-[(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(phenylmethyl)amino]pentyl]-3-(1-methylethyl)-2(3H)-furanone
361460-40-4

(3S,5S)-dihydro-5-[(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(phenylmethyl)amino]pentyl]-3-(1-methylethyl)-2(3H)-furanone

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 39 mg / H2 / Pd/C / ethanol / 48 h
10.1: ethanol / 1.5 h / 0 °C
11.1: 24 mg / NaBH4 / ethanol / 0.67 h / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C
10.1: 94 percent / H2 / Pd/C / ethanol / 18 h
11.1: ethanol / 1.5 h / 0 °C
12.1: 24 mg / NaBH4 / ethanol / 0.67 h / 20 °C
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

1,1-dimethylethyl [(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2S,4R)-tetrahydro-4-(1-methylethyl)-5-oxo-2-furanyl]pentyl]carbamate
900811-52-1

1,1-dimethylethyl [(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2S,4R)-tetrahydro-4-(1-methylethyl)-5-oxo-2-furanyl]pentyl]carbamate

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 39 mg / H2 / Pd/C / ethanol / 48 h
10.1: Et3N / tetrahydrofuran / 18 h / 20 °C
View Scheme
Multi-step reaction with 10 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 39 mg / H2 / Pd/C / ethanol / 48 h
10.1: 81 percent / Et3N / tetrahydrofuran / 18 h / 20 °C
View Scheme
Multi-step reaction with 11 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C
10.1: 94 percent / H2 / Pd/C / ethanol / 18 h
11.1: Et3N / tetrahydrofuran / 18 h / 20 °C
View Scheme
Multi-step reaction with 11 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C
10.1: 94 percent / H2 / Pd/C / ethanol / 18 h
11.1: 81 percent / Et3N / tetrahydrofuran / 18 h / 20 °C
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

phenylmethyl [(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]pentyl]carbamate
900811-45-2

phenylmethyl [(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]pentyl]carbamate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

phenylmethyl [(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2R)-tetrahydro-5-oxo-2-furanyl]pentyl]carbamate

phenylmethyl [(1S,3S)-3-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-4-methyl-1-[(2R)-tetrahydro-5-oxo-2-furanyl]pentyl]carbamate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 21 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

(5S,7S)-5-Benzyloxycarbonylamino-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-4-oxo-nonanoic acid methyl ester
900811-43-0

(5S,7S)-5-Benzyloxycarbonylamino-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-4-oxo-nonanoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

pyridin-4-yl (2S,4S)-2-[[(phenylmethoxy)carbonyl]amino]-4-methoxy-3-(3-methoxypropoxy)-γ-(1-methylethyl)benzenepentanethioate
900811-42-9

pyridin-4-yl (2S,4S)-2-[[(phenylmethoxy)carbonyl]amino]-4-methoxy-3-(3-methoxypropoxy)-γ-(1-methylethyl)benzenepentanethioate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

{(1S,3S)-1-((S)-4-Isopropylidene-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid benzyl ester
900811-49-6

{(1S,3S)-1-((S)-4-Isopropylidene-5-oxo-tetrahydro-furan-2-yl)-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid benzyl ester

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

{(1S,3S)-1-[(S)-4-(1-Hydroxy-1-methyl-ethyl)-5-oxo-tetrahydro-furan-2-yl]-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid benzyl ester

{(1S,3S)-1-[(S)-4-(1-Hydroxy-1-methyl-ethyl)-5-oxo-tetrahydro-furan-2-yl]-3-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentyl}-carbamic acid benzyl ester

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

(5S,7S)-5-Benzyloxycarbonylamino-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-4-oxo-nonanoic acid butyl ester

(5S,7S)-5-Benzyloxycarbonylamino-7-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-8-methyl-4-oxo-nonanoic acid butyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 60 percent / t-BuOH; SmI2 / tetrahydrofuran / 72 h / -78 °C
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

((1S,2S,4R)-4-Butylcarbamoyl-2-hydroxy-1-{(S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyl}-5-methyl-hexyl)-carbamic acid tert-butyl ester

((1S,2S,4R)-4-Butylcarbamoyl-2-hydroxy-1-{(S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyl}-5-methyl-hexyl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 39 mg / H2 / Pd/C / ethanol / 48 h
10.1: Et3N / tetrahydrofuran / 18 h / 20 °C
11.1: 48 percent / trimethylaluminum / CH2Cl2; toluene / 48 h / 20 °C
View Scheme
Multi-step reaction with 11 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 39 mg / H2 / Pd/C / ethanol / 48 h
10.1: 81 percent / Et3N / tetrahydrofuran / 18 h / 20 °C
11.1: 48 percent / trimethylaluminum / CH2Cl2; toluene / 48 h / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C
10.1: 94 percent / H2 / Pd/C / ethanol / 18 h
11.1: Et3N / tetrahydrofuran / 18 h / 20 °C
12.1: 48 percent / trimethylaluminum / CH2Cl2; toluene / 48 h / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C
10.1: 94 percent / H2 / Pd/C / ethanol / 18 h
11.1: 81 percent / Et3N / tetrahydrofuran / 18 h / 20 °C
12.1: 48 percent / trimethylaluminum / CH2Cl2; toluene / 48 h / 20 °C
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

(1S,2S,4S,2'S)-(4-butylcarbamoyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl}-5-methylhexyl)carbamic acid tert-butyl ester
173337-63-8

(1S,2S,4S,2'S)-(4-butylcarbamoyl-2-hydroxy-1-{2'-[4-methoxy-3-(3-methoxypropoxy)benzyl]-3-methylbutyl}-5-methylhexyl)carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 39 mg / H2 / Pd/C / ethanol / 48 h
10.1: 63 percent / Et3N / tetrahydrofuran / 18 h / 20 °C
11.1: 58 percent / trimethylaluminum / CH2Cl2; toluene / 20 h / 20 °C
View Scheme
Multi-step reaction with 12 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
3.1: 89 percent / pyridine / CH2Cl2 / 2 h / 20 °C
4.1: aq. NaOH / tetrahydrofuran; methanol / 3.5 h / 20 °C
5.1: 94 percent / EDCI / CH2Cl2 / 3.5 h / 0 °C
6.1: 67 percent / t-BuOH; SmI2 / tetrahydrofuran / 144 h / -78 °C
7.1: 85 mg / (S)-Alpine Hydride / tetrahydrofuran / 24 h / -78 °C
8.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C
8.2: 91 percent / tetrahydrofuran; hexane / 2 h / -78 °C
9.1: PCl5 / CH2Cl2 / 2.5 h / 0 °C
9.2: 32 mg / 2-hydroxypyridine; Et3N / acetonitrile / 48 h / 80 °C
10.1: 94 percent / H2 / Pd/C / ethanol / 18 h
11.1: 63 percent / Et3N / tetrahydrofuran / 18 h / 20 °C
12.1: 58 percent / trimethylaluminum / CH2Cl2; toluene / 20 h / 20 °C
View Scheme
(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene
172900-69-5

(R)-4-(2-(bromomethyl)-3-methylbutyl)-1-methoxy-2-(3-methoxypropoxy)benzene

methyl (2S,4S)-2-amino-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate
656241-36-0

methyl (2S,4S)-2-amino-4-[4-methoxy-3-(3-methoxypropoxy)benzyl]-5-methylhexanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: n-BuLi / tetrahydrofuran / -75 °C
1.2: 90 percent / tetrahydrofuran / -75 - -18 °C
2.1: 99 percent / HCl / H2O; acetonitrile
View Scheme
Multi-step reaction with 2 steps
1.1: BuLi / hexane / 0.5 h / -75 °C
1.2: 91 percent / tetrahydrofuran / 20 h / -75 - -20 °C
2.1: 90 percent / 1N HCl / acetonitrile / 1.5 h / 20 °C
View Scheme

2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene Specification

The 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene, with the CAS registry number 172900-69-5, is also known as Benzene, 4-[(2R)-2-(bromomethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)-. This chemical's molecular formula is C17H27BrO3 and molecular weight is 359.2985. Its systematic name is called 4-[(2R)-2-(bromomethyl)-3-methylbutyl]-1-methoxy-2-(3-methoxypropoxy)benzene.

Physical properties of 2-(3-Methoxypropoxy)-4-((R)-2-(bromomethyl)-3-methylbutyl)-1-methoxybenzene: (1)ACD/LogP: 4.72; (2)ACD/LogD (pH 5.5): 4.72; (3)ACD/LogD (pH 7.4): 4.72; (4)ACD/BCF (pH 5.5): 2258.19; (5)ACD/BCF (pH 7.4): 2258.19; (6)ACD/KOC (pH 5.5): 8754.22; (7)ACD/KOC (pH 7.4): 8754.22; (8)#H bond acceptors: 3; (9)#Freely Rotating Bonds: 10; (10)Index of Refraction: 1.506; (11)Molar Refractivity: 90.98 cm3; (12)Molar Volume: 306 cm3; (13)Surface Tension: 34.5 dyne/cm; (14)Density: 1.173 g/cm3; (15)Flash Point: 164.4 °C; (16)Enthalpy of Vaporization: 62.42 kJ/mol; (17)Boiling Point: 398.8 °C at 760 mmHg; (18)Vapour Pressure: 3.29E-06 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: BrC[C@@H](C(C)C)Cc1cc(OCCCOC)c(OC)cc1
(2)InChI: InChI=1/C17H27BrO3/c1-13(2)15(12-18)10-14-6-7-16(20-4)17(11-14)21-9-5-8-19-3/h6-7,11,13,15H,5,8-10,12H2,1-4H3/t15-/m0/s1
(3)InChIKey: ICJBMWOVLFPLFP-HNNXBMFYBP

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