(4S,5S)-5-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Base Information

Chemical Name:(4S,5S)-5-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde
CAS No.:338385-71-0
Molecular Formula:C₁₉H₃₀O₄Si
Molecular Weight:350.53
Hs Code.:

Synonyms:(4S,5S)-5-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

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Chemical Property of (4S,5S)-5-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

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Technology Process of (4S,5S)-5-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

There total 5 articles about (4S,5S)-5-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 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:

: phenylmagnesium bromide

: 338385-71-0
(4S,5S)-5-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 35 percent / tetrahydrofuran / -78 - 20 °C

2: 85.4 percent / imidazole / dimethylformamide / 24 h / 20 °C

3: 97 percent / H₂ / Pd/C / ethyl acetate / 6 h / 45 °C / 760 Torr

4: Dess-Martin periodinane / CH₂Cl₂ / 1 h

With 1H-imidazole; hydrogen; Dess-Martin periodane; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: Grignard reaction / 4: Dess-Martin oxidation;
DOI:10.1016/S0040-4020(01)00050-3

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 338385-71-0
(4S,5S)-5-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 85.4 percent / imidazole / dimethylformamide / 24 h / 20 °C

2: 97 percent / H₂ / Pd/C / ethyl acetate / 6 h / 45 °C / 760 Torr

3: Dess-Martin periodinane / CH₂Cl₂ / 1 h

With 1H-imidazole; hydrogen; Dess-Martin periodane; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 3: Dess-Martin oxidation;
DOI:10.1016/S0040-4020(01)00050-3

Reference yield:

: 338385-67-4
(4R)-4-hydroxy-4-phenyl-2S,3S-O-isopropylidene-butyl benzyl ether

: 338385-71-0
(4S,5S)-5-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 85.4 percent / imidazole / dimethylformamide / 24 h / 20 °C

2: 97 percent / H₂ / Pd/C / ethyl acetate / 6 h / 45 °C / 760 Torr

3: Dess-Martin periodinane / CH₂Cl₂ / 1 h

With 1H-imidazole; hydrogen; Dess-Martin periodane; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 3: Dess-Martin oxidation;
DOI:10.1016/S0040-4020(01)00050-3