(3R,5S)-2-Benzyloxy-3,5-dimethyl-cyclopentanecarboxylic acid tert-butyl ester

Base Information

• Chemical Name: (3R,5S)-2-Benzyloxy-3,5-dimethyl-cyclopentanecarboxylic acid tert-butyl ester
• CAS No.: 143949-32-0
• Molecular Formula: C₁₉H₂₈O₃
• Molecular Weight: 304.43
• Mol file: 143949-32-0.mol

Synonyms:

Chemical Property of (3R,5S)-2-Benzyloxy-3,5-dimethyl-cyclopentanecarboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S)-2-Benzyloxy-3,5-dimethyl-cyclopentanecarboxylic acid tert-butyl ester

There total 7 articles about (3R,5S)-2-Benzyloxy-3,5-dimethyl-cyclopentanecarboxylic acid tert-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(1R,2R,3S,4S)-3-Bromo-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (144016-17-1) → (3R,5S)-2-Benzyloxy-3,5-dimethyl-cyclopentanecarboxylic acid tert-butyl ester (143949-32-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 95percent H₂SO₄ / CH₂Cl₂ / 48 h / Ambient temperature

2: 1.) NaH / 1.) mineral oil, THF, 0 deg C, 20 min, 2.) mineral oil, THF, 0 deg C, 3 h

3: 96 percent / OsO₄, Me₃NO*2H₂O, water / acetone / 15 h / Ambient temperature

4: 0.54 g / NaIO₄ / tetrahydrofuran; H₂O / 1 h / 0 °C

5: BF₃*OEt₂ / CH₂Cl₂ / 18 h / 0 °C

6: 0.124 g / Raney Ni / ethanol; 1,2-dimethoxy-ethane / 2 h / Heating

With sodium periodate; osmium(VIII) oxide; trimethylamine-N-oxide; sulfuric acid; boron trifluoride diethyl etherate; water; nickel; sodium hydride; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; acetone;

DOI:10.1248/cpb.42.854

Reference yield:

(1R,2R,3S,4S)-3-Bromo-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl ester (127658-15-5) → (3R,5S)-2-Benzyloxy-3,5-dimethyl-cyclopentanecarboxylic acid tert-butyl ester (143949-32-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 2.57 g / 2N aq. NaOH / 1,2-dimethoxy-ethane; methanol / 1 h / 0 °C

2: 95percent H₂SO₄ / CH₂Cl₂ / 48 h / Ambient temperature

3: 1.) NaH / 1.) mineral oil, THF, 0 deg C, 20 min, 2.) mineral oil, THF, 0 deg C, 3 h

4: 96 percent / OsO₄, Me₃NO*2H₂O, water / acetone / 15 h / Ambient temperature

5: 0.54 g / NaIO₄ / tetrahydrofuran; H₂O / 1 h / 0 °C

6: BF₃*OEt₂ / CH₂Cl₂ / 18 h / 0 °C

7: 0.124 g / Raney Ni / ethanol; 1,2-dimethoxy-ethane / 2 h / Heating

With sodium hydroxide; sodium periodate; osmium(VIII) oxide; trimethylamine-N-oxide; sulfuric acid; boron trifluoride diethyl etherate; water; nickel; sodium hydride; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; acetone;

DOI:10.1248/cpb.42.854

Reference yield:

tert-butyl <1R-(1α,2ξ,3ξ4α)>-3-benzyloxybicyclo<2.2.1>hept-5-ene-2-carboxylate (143949-29-5) → (3R,5S)-2-Benzyloxy-3,5-dimethyl-cyclopentanecarboxylic acid tert-butyl ester (143949-32-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / OsO₄, Me₃NO*2H₂O, water / acetone / 15 h / Ambient temperature

2: 0.54 g / NaIO₄ / tetrahydrofuran; H₂O / 1 h / 0 °C

3: BF₃*OEt₂ / CH₂Cl₂ / 18 h / 0 °C

4: 0.124 g / Raney Ni / ethanol; 1,2-dimethoxy-ethane / 2 h / Heating

With sodium periodate; osmium(VIII) oxide; trimethylamine-N-oxide; boron trifluoride diethyl etherate; water; nickel; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dichloromethane; water; acetone;

DOI:10.1248/cpb.42.854

upstream raw materials:

tert-butyl (1ξ,2ξ,3R,4S)-2-benzyloxy-3,5-dicyclopentanecarboxylate

(1R,2R,3S,4S)-3-Bromo-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

(1R,2R,3S,4S)-3-Bromo-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid (S)-1-methyl-2,5-dioxo-pyrrolidin-3-yl ester

tert-butyl <1R-(1α,2β,3α,4α)>-3-bromobicyclo<2.2.1>hept-5-ene-2-carboxylate

Downstream raw materials:

methyl (3R,5S)-3,5-dimethyl-1-cyclopentenecarboxylate

(3R,5S)-2-[3-Benzenesulfonyl-2-(1-benzenesulfonyl-1H-pyrrol-3-yl)-2-hydroxy-propyl]-3,5-dimethyl-cyclopentanone