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

Base Information

• Chemical Name: (3R,5S)-6-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-hexanoic acid ethyl ester
• CAS No.: 96720-12-6
• Molecular Formula: C₂₆H₃₇BrO₅Si
• Molecular Weight: 537.566
• Mol file: 96720-12-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (3R,5S)-6-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-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: 94.0%

(3R,5S)-6-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-hexanoic acid ethyl ester (96720-11-5) + chloromethyl methyl ether (107-30-2) → (3R,5S)-6-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-hexanoic acid ethyl ester (96720-12-6)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In acetonitrile; at -3 ℃; for 24h;

DOI:10.1016/S0040-4039(00)98429-6

Reference yield:

(E)-ethyl 4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate (96720-07-9) → (3R,5S)-6-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-hexanoic acid ethyl ester (96720-12-6)

Guidance literature:

Multi-step reaction with 5 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

5: 94 percent / i-Pr₂NEt, DMAP / acetonitrile / 24 h / -3 °C

With hydrogenchloride; dmap; dimethylboron bromide; sodium ethanolate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(00)98429-6

Reference yield:

ethyl (S,E)-5,6-dihydroxy-2-hexenoate (96720-08-0) → (3R,5S)-6-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-hexanoic acid ethyl ester (96720-12-6)

Guidance literature:

Multi-step reaction with 4 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

4: 94 percent / i-Pr₂NEt, DMAP / acetonitrile / 24 h / -3 °C

With dmap; dimethylboron bromide; sodium ethanolate; triethylamine; N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)98429-6

upstream raw materials:

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

chloromethyl methyl ether

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

ethyl 6-<(tert-butyldiphenylsilyl)oxy>-5(S,E)-hydroxy-2-hexenoate

Downstream raw materials:

7-(2,4-Dichlorophenyl)-D-erythro-3-hydroxy-5-heptanolide

(3R,5R)-7-(2,4-Dichloro-phenyl)-5-hydroxy-3-methoxymethoxy-heptanoic acid ethyl ester

6(R)-[2-(2,4-dichlorophenyl)ethyl]-4(R)-(methoxymethoxy)tetrahydro-2H-pyran-2-one