(S)-(E)-tert-butyl 3-(tert-butyldiphenylsilyl)oxy-6-iodo-hex-5-enoate

Base Information

• Chemical Name: (S)-(E)-tert-butyl 3-(tert-butyldiphenylsilyl)oxy-6-iodo-hex-5-enoate
• CAS No.: 262279-26-5
• Molecular Formula: C₂₆H₃₅IO₃Si
• Molecular Weight: 550.552
• Mol file: 262279-26-5.mol

Synonyms:(S)-(E)-tert-butyl 3-(tert-butyldiphenylsilyl)oxy-6-iodo-hex-5-enoate

Chemical Property of (S)-(E)-tert-butyl 3-(tert-butyldiphenylsilyl)oxy-6-iodo-hex-5-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(E)-tert-butyl 3-(tert-butyldiphenylsilyl)oxy-6-iodo-hex-5-enoate

There total 5 articles about (S)-(E)-tert-butyl 3-(tert-butyldiphenylsilyl)oxy-6-iodo-hex-5-enoate 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: 100.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (R)-tert-butyl 3,4-epoxybutanoate (108100-50-1) → (S)-(E)-tert-butyl 3-(tert-butyldiphenylsilyl)oxy-6-iodo-hex-5-enoate (262279-26-5)

Guidance literature:

(R)-tert-butyl 3,4-epoxybutanoate; Bu₃Sn-[(E)-CH=CH]-Cu(Th)CNLi₂; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1.5h;

tert-butylchlorodiphenylsilane; With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;

With iodine; In tetrahydrofuran; at 0 ℃; for 0.5h; Further stages.;

DOI:10.1021/ja002377a

Reference yield: 98.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (E)-(S)-3-Hydroxy-6-iodo-hex-5-enoic acid tert-butyl ester (262279-29-8) → (S)-(E)-tert-butyl 3-(tert-butyldiphenylsilyl)oxy-6-iodo-hex-5-enoate (262279-26-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/ja994003r

Reference yield:

t-butyl vinylacetate (14036-55-6) → (S)-(E)-tert-butyl 3-(tert-butyldiphenylsilyl)oxy-6-iodo-hex-5-enoate (262279-26-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 28.4 g / m-CPBA / CHCl₃ / 20 °C

2.1: 94 percent / AcOH; water / (R,R)-salen-Co / 12 h / 20 °C

3.1: tetrahydrofuran; diethyl ether / 1.5 h / -78 °C

3.2: imidazole / dimethylformamide / 20 °C

3.3: 100 percent / iodine / tetrahydrofuran / 0.5 h / 0 °C

With water; acetic acid; 3-chloro-benzenecarboperoxoic acid; (R,R)-Salen-Co; In tetrahydrofuran; diethyl ether; chloroform;

DOI:10.1021/ja002377a

upstream raw materials:

tert-butylchlorodiphenylsilane

(E)-(S)-3-Hydroxy-6-iodo-hex-5-enoic acid tert-butyl ester

(R)-tert-butyl 3,4-epoxybutanoate

t-butyl vinylacetate

Downstream raw materials:

(3S,8S,9S)-(E)-tert-butyl 3-(tert-butyldiphenylsiloxy)-7-hydroxy-8-methyl-9-methoxy-9-(tert-butyldiphenylsiloxymethyl-2,4'-trisoxazole-4'-yl)-non-5-enoate

(3S,8R,9S)-(E)-3-(tert-butyldiphenylsiloxy)-7-oxo-8-methyl-9-methoxy-9-(2-bromomethyl-2,4'-trisoxazole-4'-yl)-non-5-enoic acid

(3S,8R,9S)-(E)-tert-butyl 3-(tert-butyldiphenylsiloxy)-7-oxo-8-methyl-9-methoxy-9-(2-bromomethyl-2,4'-trisoxazole-4'-yl)-non-5-enoate

(3S,8R,9S)-(E)-tert-butyl 3-(tert-butyldiphenylsiloxy)-7-oxo-8-methyl-9-methoxy-9-(2-hydroxymethyl-2,4'-trisoxazole-4'-yl)-non-5-enoate