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

Base Information

• Chemical Name: tert-butyl (1ξ,2ξ,3R,4S)-2-benzyloxy-3,5-dicyclopentanecarboxylate
• CAS No.: 143949-31-9
• Molecular Formula: C₂₇H₄₄O₃S₄
• Molecular Weight: 544.909
• Mol file: 143949-31-9.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about tert-butyl (1ξ,2ξ,3R,4S)-2-benzyloxy-3,5-dicyclopentanecarboxylate 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) → tert-butyl (1ξ,2ξ,3R,4S)-2-benzyloxy-3,5-dicyclopentanecarboxylate (143949-31-9)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1248/cpb.42.854

Reference yield:

tert-butyl <1R-(1α,2β,3α,4α)>-3-bromobicyclo<2.2.1>hept-5-ene-2-carboxylate (143949-28-4) → tert-butyl (1ξ,2ξ,3R,4S)-2-benzyloxy-3,5-dicyclopentanecarboxylate (143949-31-9)

Guidance literature:

Multi-step reaction with 4 steps

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

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

3: 0.54 g / NaIO₄ / tetrahydrofuran; H₂O / 1 h / 0 °C

4: BF₃*OEt₂ / CH₂Cl₂ / 18 h / 0 °C

With sodium periodate; osmium(VIII) oxide; trimethylamine-N-oxide; boron trifluoride diethyl etherate; water; sodium hydride; In tetrahydrofuran; 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) → tert-butyl (1ξ,2ξ,3R,4S)-2-benzyloxy-3,5-dicyclopentanecarboxylate (143949-31-9)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1248/cpb.42.854

upstream raw materials:

ethanethiol

(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:

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

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