tert-butyl (2S,3R,4R)-3-{[(tert-butyl)dimethylsilyl]oxy}-4-hydroxy-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate

Base Information

Chemical Name:tert-butyl (2S,3R,4R)-3-{[(tert-butyl)dimethylsilyl]oxy}-4-hydroxy-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate
CAS No.:865814-21-7
Molecular Formula:C₂₃H₃₉NO₅Si
Molecular Weight:437.652
Hs Code.:

Synonyms:tert-butyl (2S,3R,4R)-3-{[(tert-butyl)dimethylsilyl]oxy}-4-hydroxy-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate

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Chemical Property of tert-butyl (2S,3R,4R)-3-{[(tert-butyl)dimethylsilyl]oxy}-4-hydroxy-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate

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Technology Process of tert-butyl (2S,3R,4R)-3-{[(tert-butyl)dimethylsilyl]oxy}-4-hydroxy-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate

There total 4 articles about tert-butyl (2S,3R,4R)-3-{[(tert-butyl)dimethylsilyl]oxy}-4-hydroxy-2-(4-methoxybenzyl)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:

: 865814-16-0
tert-butyl (2S)-2-(4-methoxybenzyl)-3-oxopyrrolidine-1-carboxylate

: 865814-21-7
tert-butyl (2S,3R,4R)-3-{[(tert-butyl)dimethylsilyl]oxy}-4-hydroxy-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: BuLi; iPr₂NH / hexane; tetrahydrofuran / 0.33 h / -78 °C

1.2: 56 percent / DMPU / hexane; tetrahydrofuran / -78 - 20 °C

2.1: BH₃*THF / tetrahydrofuran / -30 - 20 °C

2.2: 81 percent / NaOH; aq. H₂O₂ / tetrahydrofuran / 16 h / 20 °C

With n-butyllithium; borane-THF; diisopropylamine; In tetrahydrofuran; hexane;
DOI:10.1002/hlca.200590143

Reference yield:

: 865814-13-7
(2S)-3-O-{[1-(tert-butoxy)carbonyl]-2,5-dihydro-2-(4-methoxybenzyl)-1H-pyrrol-3-yl}-1,2:4,5-di-O-isopropylidene-β-D-fructopyranose

: 865814-21-7
tert-butyl (2S,3R,4R)-3-{[(tert-butyl)dimethylsilyl]oxy}-4-hydroxy-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 66 percent / aq. HCl / tetrahydrofuran / 20 °C

2.1: BuLi; iPr₂NH / hexane; tetrahydrofuran / 0.33 h / -78 °C

2.2: 56 percent / DMPU / hexane; tetrahydrofuran / -78 - 20 °C

3.1: BH₃*THF / tetrahydrofuran / -30 - 20 °C

3.2: 81 percent / NaOH; aq. H₂O₂ / tetrahydrofuran / 16 h / 20 °C

With hydrogenchloride; n-butyllithium; borane-THF; diisopropylamine; In tetrahydrofuran; hexane;
DOI:10.1002/hlca.200590143

Reference yield:

: 3-O-{2-{[(tert-butoxy)carbonyl]amino}-1-ethenylidene-3-(4-methoxyphenyl)propyl}-1,2:4,5-di-O-isopropylidene-β-D-fructopyranose

: 865814-21-7
tert-butyl (2S,3R,4R)-3-{[(tert-butyl)dimethylsilyl]oxy}-4-hydroxy-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 14 percent / t-BuOK / dimethylsulfoxide / 16 h / 50 °C

2.1: 66 percent / aq. HCl / tetrahydrofuran / 20 °C

3.1: BuLi; iPr₂NH / hexane; tetrahydrofuran / 0.33 h / -78 °C

3.2: 56 percent / DMPU / hexane; tetrahydrofuran / -78 - 20 °C

4.1: BH₃*THF / tetrahydrofuran / -30 - 20 °C

4.2: 81 percent / NaOH; aq. H₂O₂ / tetrahydrofuran / 16 h / 20 °C

With hydrogenchloride; n-butyllithium; borane-THF; potassium tert-butylate; diisopropylamine; In tetrahydrofuran; hexane; dimethyl sulfoxide;
DOI:10.1002/hlca.200590143