(3S,4R)-2-bromo-4-((4-methoxybenzyl)oxy)-3-(oct-2-yn-1-yl)cyclopentanone

Base Information

Chemical Name:(3S,4R)-2-bromo-4-((4-methoxybenzyl)oxy)-3-(oct-2-yn-1-yl)cyclopentanone
CAS No.:1605291-88-0
Molecular Formula:C₂₁H₂₇BrO₃
Molecular Weight:407.348
Hs Code.:

Synonyms:(3S,4R)-2-bromo-4-((4-methoxybenzyl)oxy)-3-(oct-2-yn-1-yl)cyclopentanone

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Chemical Property of (3S,4R)-2-bromo-4-((4-methoxybenzyl)oxy)-3-(oct-2-yn-1-yl)cyclopentanone

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Technology Process of (3S,4R)-2-bromo-4-((4-methoxybenzyl)oxy)-3-(oct-2-yn-1-yl)cyclopentanone

There total 6 articles about (3S,4R)-2-bromo-4-((4-methoxybenzyl)oxy)-3-(oct-2-yn-1-yl)cyclopentanone 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:

: 1605291-83-5
(3S,4R)-2-bromo-4-((4-methoxybenzyl)oxy)-3-(oct-2-yn-1-yl)cyclopentanol

: 1605291-87-9
(3S,4R)-2-bromo-4-((4-methoxybenzyl)oxy)-3-(oct-2-yn-1-yl)cyclopentanone

: 1605291-88-0
(3S,4R)-2-bromo-4-((4-methoxybenzyl)oxy)-3-(oct-2-yn-1-yl)cyclopentanone

Guidance literature:: With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 15h; Overall yield = 93 %; Overall yield = 167 mg; Optical yield = 20 %de;
DOI:10.1021/ol500654g

Reference yield:

: 1605291-78-8
2-((1R,5R)-5-((4-methoxybenzyl)oxy)cyclopent-2-en-1-yl)-N,N-dimethylacetamide

: 1605291-87-9
(3S,4R)-2-bromo-4-((4-methoxybenzyl)oxy)-3-(oct-2-yn-1-yl)cyclopentanone

: 1605291-88-0
(3S,4R)-2-bromo-4-((4-methoxybenzyl)oxy)-3-(oct-2-yn-1-yl)cyclopentanone

Guidance literature:: Multi-step reaction with 6 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -105 °C

2.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

4.2: 2 h / -78 - 20 °C

5.1: N-Bromosuccinimide; sodium hydrogencarbonate / dimethyl sulfoxide; water / 12 h / 0 - 20 °C

6.1: pyridinium chlorochromate / dichloromethane / 15 h / 20 °C

With N-Bromosuccinimide; n-butyllithium; diisobutylaluminium hydride; sodium hydrogencarbonate; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; 2.1: |Corey-Fuchs Alkyne Synthesis;
DOI:10.1021/ol500654g

Reference yield:

: 1605291-79-9
2-((1R,5R)-5-((4-methoxybenzyl)oxy)cyclopent-2-en-1-yl)acetaldehyde

: 1605291-87-9
(3S,4R)-2-bromo-4-((4-methoxybenzyl)oxy)-3-(oct-2-yn-1-yl)cyclopentanone

: 1605291-88-0
(3S,4R)-2-bromo-4-((4-methoxybenzyl)oxy)-3-(oct-2-yn-1-yl)cyclopentanone

Guidance literature:: Multi-step reaction with 5 steps

1.1: triphenylphosphine / dichloromethane / 0.17 h / 0 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: 2 h / -78 - 20 °C

4.1: N-Bromosuccinimide; sodium hydrogencarbonate / dimethyl sulfoxide; water / 12 h / 0 - 20 °C

5.1: pyridinium chlorochromate / dichloromethane / 15 h / 20 °C

With N-Bromosuccinimide; n-butyllithium; sodium hydrogencarbonate; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; 1.1: |Corey-Fuchs Alkyne Synthesis;
DOI:10.1021/ol500654g