benzyl (2S,3S)-2-(3-hydroxy-4-(toluene-4-sulfonyloxy)butyl)-3-[(R)-1-(2,4,6-triisopropylphenyl)ethoxy]pyrrolidine-1-carboxylate

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Chemical Name:benzyl (2S,3S)-2-(3-hydroxy-4-(toluene-4-sulfonyloxy)butyl)-3-[(R)-1-(2,4,6-triisopropylphenyl)ethoxy]pyrrolidine-1-carboxylate
CAS No.:306739-95-7
Molecular Formula:C₄₀H₅₅NO₇S
Molecular Weight:693.945
Hs Code.:

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

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

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

There total 7 articles about benzyl (2S,3S)-2-(3-hydroxy-4-(toluene-4-sulfonyloxy)butyl)-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: 94.0%

: 98-59-9
p-toluenesulfonyl chloride

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

: 306739-95-7
benzyl (2S,3S)-2-(3-hydroxy-4-(toluene-4-sulfonyloxy)butyl)-3-[(R)-1-(2,4,6-triisopropylphenyl)ethoxy]pyrrolidine-1-carboxylate

Guidance literature:: benzyl (2S,3S)-2-(3,4-dihydroxybutyl)-3-[(R)-1-(2,4,6-triisopropylphenyl)ethoxy]pyrrolidine-1-carboxylate; With di(n-butyl)tin oxide; In methanol; for 0.75h; Heating;

p-toluenesulfonyl chloride; With triethylamine; for 0.166667h; Further stages.;
DOI:10.1021/jo0005621

Reference yield:

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

: 306739-95-7
benzyl (2S,3S)-2-(3-hydroxy-4-(toluene-4-sulfonyloxy)butyl)-3-[(R)-1-(2,4,6-triisopropylphenyl)ethoxy]pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 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

5.1: dibutyltin oxide / methanol / 0.75 h / Heating

5.2: 94 percent / Et₃N / 0.17 h

With osmium(VIII) oxide; n-butyllithium; trimethylamine-N-oxide; boron trifluoride diethyl etherate; di(n-butyl)tin oxide; lithium triethylborohydride; In tetrahydrofuran; methanol; hexane; dichloromethane; tert-butyl alcohol; 1.1: Metallation / 1.2: Acylation / 2.1: Reduction / 3.1: dehydroxylation / 4.1: dihydroxylation / 5.1: stannylation / 5.2: Tosylation;
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

: 306739-95-7
benzyl (2S,3S)-2-(3-hydroxy-4-(toluene-4-sulfonyloxy)butyl)-3-[(R)-1-(2,4,6-triisopropylphenyl)ethoxy]pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 5 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

5.1: dibutyltin oxide / methanol / 0.75 h / Heating

5.2: 94 percent / Et₃N / 0.17 h

With osmium(VIII) oxide; n-butyllithium; trimethylamine-N-oxide; boron trifluoride diethyl etherate; di(n-butyl)tin oxide; lithium triethylborohydride; In tetrahydrofuran; methanol; hexane; dichloromethane; tert-butyl alcohol; 1.1: Metallation / 1.2: Acylation / 2.1: Reduction / 3.1: dehydroxylation / 4.1: dihydroxylation / 5.1: stannylation / 5.2: Tosylation;
DOI:10.1021/jo0005621