tert-butyl (3aR,4R,6aS)-4-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate

Base Information

Chemical Name:tert-butyl (3aR,4R,6aS)-4-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate
CAS No.:933055-19-7
Molecular Formula:C₂₉H₄₁NO₅Si
Molecular Weight:511.734
Hs Code.:

Synonyms:tert-butyl (3aR,4R,6aS)-4-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate

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Chemical Property of tert-butyl (3aR,4R,6aS)-4-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate

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Technology Process of tert-butyl (3aR,4R,6aS)-4-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate

There total 12 articles about tert-butyl (3aR,4R,6aS)-4-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-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: 91.0%

: 852616-66-1
tert-butyl (2R,3R,4S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-3,4-dihydroxypyrrolidine-1-carboxylate

: 77-76-9
2,2-dimethoxy-propane

: 933055-19-7
tert-butyl (3aR,4R,6aS)-4-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate

Guidance literature:: With toluene-4-sulfonic acid; In acetone; at 20 ℃;
DOI:10.3390/molecules24050873

Reference yield:

: 852616-64-9
tert-butyl (S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,5-dihydro-1H-pyrrole-1-carboxylate

: 933055-19-7
tert-butyl (3aR,4R,6aS)-4-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / OsO₄; 4-methylmorpholine N-oxide monohydrate / acetone; H₂O; 2-methyl-propan-2-ol / 48 h

2: 85 percent / p-toluenesulfonic acid / acetone / 4 h

With osmium(VIII) oxide; toluene-4-sulfonic acid; 4-methylmorpholine 4-oxide monohydrate; In water; acetone; tert-butyl alcohol;
DOI:10.1016/j.tetasy.2006.12.023

Reference yield:

: 920009-47-8
(2S,3S)-3-(N-allyl-N-tert-butoxycarbonyl)amino-4-pentene-1,2-diol

: 933055-19-7
tert-butyl (3aR,4R,6aS)-4-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-5H-[1,3]dioxolo[4,5-c]pyrrole-5-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / Grubbs first generation catalyst / CH₂Cl₂ / 4 h / 40 °C

2.1: NaIO₄ / tetrahydrofuran; H₂O / 2 h

2.2: 30 percent / LiBH₄ / methanol; diethyl ether / 4 h

3.1: 94 percent / imidazole / dimethylformamide / 24 h

4.1: 80 percent / OsO₄; 4-methylmorpholine N-oxide monohydrate / acetone; H₂O; 2-methyl-propan-2-ol / 48 h

5.1: 85 percent / p-toluenesulfonic acid / acetone / 4 h

With 1H-imidazole; sodium periodate; osmium(VIII) oxide; toluene-4-sulfonic acid; 4-methylmorpholine 4-oxide monohydrate; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 1.1: olefin metathesis;
DOI:10.1016/j.tetasy.2006.12.023