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

Base Information

Chemical Name:ethyl 7S-t-butyldimethylsilyloxy-7-phenyl-5S,6S-O-isopropylidene-4S-hydroxy-heptyn-2-oate
CAS No.:338385-72-1
Molecular Formula:C₂₄H₃₆O₆Si
Molecular Weight:448.632
Hs Code.:

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

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

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

There total 7 articles about ethyl 7S-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: 31.6%

: 338385-70-9
(4S,5S)-5-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

: 623-47-2
propynoic acid ethyl ester

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

: 338385-72-1
ethyl 7S-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-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde; In tetrahydrofuran; at -78 ℃; for 12h;
DOI:10.1016/S0040-4020(01)00050-3

Reference yield:

: 81801-09-4
4-O-benzyl-2,3-O-isopropylidene-D-threose

: 338385-72-1
ethyl 7S-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: 88 percent / imidazole / dimethylformamide / 24 h / 20 °C

3.1: 91 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: 31.6 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

: 338385-72-1
ethyl 7S-t-butyldimethylsilyloxy-7-phenyl-5S,6S-O-isopropylidene-4S-hydroxy-heptyn-2-oate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 88 percent / imidazole / dimethylformamide / 24 h / 20 °C

2.1: 91 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: 31.6 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