(3R,5S)-6-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-hexanoic acid ethyl ester

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Chemical Name:(3R,5S)-6-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-hexanoic acid ethyl ester
CAS No.:96720-11-5
Molecular Formula:C₂₄H₃₃BrO₄Si
Molecular Weight:493.513
Hs Code.:

Synonyms:(3R,5S)-6-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-hexanoic acid ethyl ester

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Chemical Property of (3R,5S)-6-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-hexanoic acid ethyl ester

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Technology Process of (3R,5S)-6-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-hexanoic acid ethyl ester

There total 5 articles about (3R,5S)-6-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-hexanoic acid ethyl ester 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: 82.0%

: 96720-10-4
[(2R,4S)-4-(tert-Butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-yl]-acetic acid ethyl ester

: 96720-11-5
(3R,5S)-6-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-hexanoic acid ethyl ester

Guidance literature:: With dimethylboron bromide; In dichloromethane; 0 deg C 10 min, then RT, 2 h;
DOI:10.1016/S0040-4039(00)98429-6

Reference yield:

: 96720-07-9
(E)-ethyl 4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate

: 96720-11-5
(3R,5S)-6-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-hexanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: HCl / H₂O; tetrahydrofuran / 18 h / Ambient temperature

2: Et₃N, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

3: NaOEt / ethanol / Heating; RT, 2 h, then reflux 4 h

4: 82 percent / dimethylboron bromide / CH₂Cl₂ / 0 deg C 10 min, then RT, 2 h

With hydrogenchloride; dmap; dimethylboron bromide; sodium ethanolate; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water;
DOI:10.1016/S0040-4039(00)98429-6

Reference yield:

: 96720-08-0
ethyl (S,E)-5,6-dihydroxy-2-hexenoate

: 96720-11-5
(3R,5S)-6-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-hexanoic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: Et₃N, DMAP / CH₂Cl₂ / 18 h / Ambient temperature

2: NaOEt / ethanol / Heating; RT, 2 h, then reflux 4 h

3: 82 percent / dimethylboron bromide / CH₂Cl₂ / 0 deg C 10 min, then RT, 2 h

With dmap; dimethylboron bromide; sodium ethanolate; triethylamine; In ethanol; dichloromethane;
DOI:10.1016/S0040-4039(00)98429-6