(3aR,4R,6S,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-6-(3-ethenylphenyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole

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Chemical Name:(3aR,4R,6S,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-6-(3-ethenylphenyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole
CAS No.:1360619-11-9
Molecular Formula:C₂₂H₃₅NO₃Si
Molecular Weight:389.61
Hs Code.:

Synonyms:(3aR,4R,6S,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-6-(3-ethenylphenyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole

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Chemical Property of (3aR,4R,6S,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-6-(3-ethenylphenyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole

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Technology Process of (3aR,4R,6S,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-6-(3-ethenylphenyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole

There total 3 articles about (3aR,4R,6S,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-6-(3-ethenylphenyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole 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: 56.0%

: 153172-31-7
(3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole

: (3-ethenylphenyl)magnesium bromide

: 1360619-11-9
(3aR,4R,6S,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-6-(3-ethenylphenyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole

Guidance literature:: (3aR,4R,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole; With N-chloro-succinimide; In pentane; at 20 ℃; for 0.5h;

With 2,2,6,6-tetramethylpiperidinyl-lithium; In tetrahydrofuran; hexane; at -78 ℃; for 5h;

(3-ethenylphenyl)magnesium bromide; In tetrahydrofuran; at -78 - 0 ℃; for 16h;
DOI:10.1002/hlca.201100415

Reference yield:

: 105990-41-8,186759-56-8,187339-50-0
(2R,3R,4S)-2-hydroxymethylpyrrolidine-3,4-diol

: 1360619-11-9
(3aR,4R,6S,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-6-(3-ethenylphenyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole

Guidance literature:: Multi-step reaction with 3 steps

1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 3 h / 20 °C

2.1: 1H-imidazole / dichloromethane / 12 h / 20 °C

3.1: N-chloro-succinimide / pentane / 0.5 h / 20 °C

3.2: 5 h / -78 °C

3.3: 16 h / -78 - 0 °C

With 1H-imidazole; N-chloro-succinimide; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1002/hlca.201100415

Reference yield:

: 117859-48-0
C₈H₁₅NO₃

: 1360619-11-9
(3aR,4R,6S,6aS)-4-({[(tert-butyl)(dimethyl)silyl]oxy}methyl)-6-(3-ethenylphenyl)tetrahydro-2,2-dimethyl-3aH-[1,3]dioxolo[4,5-c]pyrrole

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1H-imidazole / dichloromethane / 12 h / 20 °C

2.1: N-chloro-succinimide / pentane / 0.5 h / 20 °C

2.2: 5 h / -78 °C

2.3: 16 h / -78 - 0 °C

With 1H-imidazole; N-chloro-succinimide; In dichloromethane; pentane;
DOI:10.1002/hlca.201100415