benzyl (2S,3S)-2-(3,4-dihydroxybutyl)-3-[(R)-1-(2,4,6-triisopropylphenyl)ethoxy]pyrrolidine-1-carboxylate

Base Information

Chemical Name:benzyl (2S,3S)-2-(3,4-dihydroxybutyl)-3-[(R)-1-(2,4,6-triisopropylphenyl)ethoxy]pyrrolidine-1-carboxylate
CAS No.:306739-93-5
Molecular Formula:C₃₃H₄₉NO₅
Molecular Weight:539.756
Hs Code.:

Synonyms:benzyl (2S,3S)-2-(3,4-dihydroxybutyl)-3-[(R)-1-(2,4,6-triisopropylphenyl)ethoxy]pyrrolidine-1-carboxylate

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Chemical Property of benzyl (2S,3S)-2-(3,4-dihydroxybutyl)-3-[(R)-1-(2,4,6-triisopropylphenyl)ethoxy]pyrrolidine-1-carboxylate

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Technology Process of benzyl (2S,3S)-2-(3,4-dihydroxybutyl)-3-[(R)-1-(2,4,6-triisopropylphenyl)ethoxy]pyrrolidine-1-carboxylate

There total 6 articles about benzyl (2S,3S)-2-(3,4-dihydroxybutyl)-3-[(R)-1-(2,4,6-triisopropylphenyl)ethoxy]pyrrolidine-1-carboxylate 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: 67.0%

: 306739-82-2
benzyl (2S,3S)-2-but-3-enyl-3-[(R)-1-(2,4,6-triisopropylphenyl)ethoxy]pyrrolidine-1-carboxylate

: 306739-93-5
benzyl (2S,3S)-2-(3,4-dihydroxybutyl)-3-[(R)-1-(2,4,6-triisopropylphenyl)ethoxy]pyrrolidine-1-carboxylate

Guidance literature:: With osmium(VIII) oxide; trimethylamine-N-oxide; In tert-butyl alcohol; for 12h; Heating;
DOI:10.1021/jo0005621

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 306739-93-5
benzyl (2S,3S)-2-(3,4-dihydroxybutyl)-3-[(R)-1-(2,4,6-triisopropylphenyl)ethoxy]pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 92 percent / tetrahydrofuran / 1 h / 0 °C

2.1: 2.06 g / LiBEt₃H / tetrahydrofuran / 0.5 h / -78 °C

3.1: 1.50 g / BF₃*OEt₂ / CH₂Cl₂ / 2 h / -78 °C

4.1: 67 percent / OsO₄; Me₃NO*2H₂O / 2-methyl-propan-2-ol / 12 h / Heating

With osmium(VIII) oxide; n-butyllithium; trimethylamine-N-oxide; boron trifluoride diethyl etherate; lithium triethylborohydride; In tetrahydrofuran; hexane; dichloromethane; tert-butyl alcohol; 1.1: Metallation / 1.2: Acylation / 2.1: Reduction / 3.1: dehydroxylation / 4.1: dihydroxylation;
DOI:10.1021/jo0005621

Reference yield:

: 306739-88-8
(4S,5S)-5-but-3-enyl-4-[(R)-1-(2,4,6-triisopropylphenyl)ethoxy]pyrrolidin-2-one

: 306739-93-5
benzyl (2S,3S)-2-(3,4-dihydroxybutyl)-3-[(R)-1-(2,4,6-triisopropylphenyl)ethoxy]pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 92 percent / tetrahydrofuran / 1 h / 0 °C

2.1: 2.06 g / LiBEt₃H / tetrahydrofuran / 0.5 h / -78 °C

3.1: 1.50 g / BF₃*OEt₂ / CH₂Cl₂ / 2 h / -78 °C

4.1: 67 percent / OsO₄; Me₃NO*2H₂O / 2-methyl-propan-2-ol / 12 h / Heating

With osmium(VIII) oxide; n-butyllithium; trimethylamine-N-oxide; boron trifluoride diethyl etherate; lithium triethylborohydride; In tetrahydrofuran; hexane; dichloromethane; tert-butyl alcohol; 1.1: Metallation / 1.2: Acylation / 2.1: Reduction / 3.1: dehydroxylation / 4.1: dihydroxylation;
DOI:10.1021/jo0005621