ethyl 7R-t-butyldimethylsilyloxy-7-phenyl-5S,6S-O-isopropylidene-4S-hydroxy-heptyn-2-oate

Base Information

Chemical Name:ethyl 7R-t-butyldimethylsilyloxy-7-phenyl-5S,6S-O-isopropylidene-4S-hydroxy-heptyn-2-oate
CAS No.:338385-74-3
Molecular Formula:C₂₄H₃₆O₆Si
Molecular Weight:448.632
Hs Code.:

Synonyms:ethyl 7R-t-butyldimethylsilyloxy-7-phenyl-5S,6S-O-isopropylidene-4S-hydroxy-heptyn-2-oate

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Chemical Property of ethyl 7R-t-butyldimethylsilyloxy-7-phenyl-5S,6S-O-isopropylidene-4S-hydroxy-heptyn-2-oate

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Technology Process of ethyl 7R-t-butyldimethylsilyloxy-7-phenyl-5S,6S-O-isopropylidene-4S-hydroxy-heptyn-2-oate

There total 6 articles about ethyl 7R-t-butyldimethylsilyloxy-7-phenyl-5S,6S-O-isopropylidene-4S-hydroxy-heptyn-2-oate 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: 79.0%

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

: 623-47-2
propynoic acid ethyl ester

: (R)-4-{(4R,5S)-5-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-hydroxy-but-2-ynoic acid ethyl ester

: 338385-74-3
ethyl 7R-t-butyldimethylsilyloxy-7-phenyl-5S,6S-O-isopropylidene-4S-hydroxy-heptyn-2-oate

Guidance literature:: propynoic acid ethyl ester; With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 1 ℃;

(4S,5S)-5-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde; In tetrahydrofuran; at -78 ℃; for 12h; Title compound not separated from byproducts;
DOI:10.1016/S0040-4020(01)00050-3

Reference yield:

: phenylmagnesium bromide

: 338385-74-3
ethyl 7R-t-butyldimethylsilyloxy-7-phenyl-5S,6S-O-isopropylidene-4S-hydroxy-heptyn-2-oate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 35 percent / tetrahydrofuran / -78 - 20 °C

2.1: 85.4 percent / imidazole / dimethylformamide / 24 h / 20 °C

3.1: 97 percent / H₂ / Pd/C / ethyl acetate / 6 h / 45 °C / 760 Torr

4.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

5.1: lithium diisopropylamide / tetrahydrofuran / -78 - 1 °C

5.2: 79 percent / tetrahydrofuran / 12 h / -78 °C

With 1H-imidazole; hydrogen; Dess-Martin periodane; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1.1: Grignard reaction / 4.1: Dess-Martin oxidation;
DOI:10.1016/S0040-4020(01)00050-3

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 338385-74-3
ethyl 7R-t-butyldimethylsilyloxy-7-phenyl-5S,6S-O-isopropylidene-4S-hydroxy-heptyn-2-oate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 85.4 percent / imidazole / dimethylformamide / 24 h / 20 °C

2.1: 97 percent / H₂ / Pd/C / ethyl acetate / 6 h / 45 °C / 760 Torr

3.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

4.1: lithium diisopropylamide / tetrahydrofuran / -78 - 1 °C

4.2: 79 percent / tetrahydrofuran / 12 h / -78 °C

With 1H-imidazole; hydrogen; Dess-Martin periodane; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 3.1: Dess-Martin oxidation;
DOI:10.1016/S0040-4020(01)00050-3