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

Base Information

Chemical Name:(3S,4R)-2-bromo-4-((4-methoxybenzyl)oxy)-3-(oct-2-yn-1-yl)cyclopentanol
CAS No.:1605291-83-5
Molecular Formula:C₂₁H₂₉BrO₃
Molecular Weight:409.363
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

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

There total 13 articles about (3S,4R)-2-bromo-4-((4-methoxybenzyl)oxy)-3-(oct-2-yn-1-yl)cyclopentanol 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:

: 1605291-82-4
1-methoxy-4-((((1R,2R)-2-(oct-2-yn-1-yl)cyclopent-3-en-1-yl)oxy)methyl)benzene

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

: 1605291-84-6
C₂₁H₂₉BrO₃

: 123-11-5
4-methoxy-benzaldehyde

Guidance literature:: With N-Bromosuccinimide; sodium hydrogencarbonate; In water; dimethyl sulfoxide; at 0 - 20 ℃; for 12h; regioselective reaction;
DOI:10.1021/ol500654g

Reference yield:

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

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

: 1605291-84-6
C₂₁H₂₉BrO₃

: 123-11-5
4-methoxy-benzaldehyde

Guidance literature:: Multi-step reaction with 5 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

With N-Bromosuccinimide; n-butyllithium; diisobutylaluminium hydride; sodium hydrogencarbonate; triphenylphosphine; 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

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

: 1605291-84-6
C₂₁H₂₉BrO₃

: 123-11-5
4-methoxy-benzaldehyde

Guidance literature:: Multi-step reaction with 4 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

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