(1E,2-endo,3-exo,6-endo)-6-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-2-(4,5-dihydro-2-furanyl)-1-<2-(4-methoxyphenoxy)ethenyl>-3-methyl-3-(phenylthio)-7-oxabicyclo<2.2.1>heptan-2-ol

Base Information

• Chemical Name: (1E,2-endo,3-exo,6-endo)-6-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-2-(4,5-dihydro-2-furanyl)-1-<2-(4-methoxyphenoxy)ethenyl>-3-methyl-3-(phenylthio)-7-oxabicyclo<2.2.1>heptan-2-ol
• CAS No.: 142041-48-3
• Molecular Formula: C₄₂H₄₆O₆SSi
• Molecular Weight: 706.975

Synonyms:

Chemical Property of (1E,2-endo,3-exo,6-endo)-6-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-2-(4,5-dihydro-2-furanyl)-1-<2-(4-methoxyphenoxy)ethenyl>-3-methyl-3-(phenylthio)-7-oxabicyclo<2.2.1>heptan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (1E,2-endo,3-exo,6-endo)-6-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-2-(4,5-dihydro-2-furanyl)-1-<2-(4-methoxyphenoxy)ethenyl>-3-methyl-3-(phenylthio)-7-oxabicyclo<2.2.1>heptan-2-ol

There total 8 articles about (1E,2-endo,3-exo,6-endo)-6-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-2-(4,5-dihydro-2-furanyl)-1-<2-(4-methoxyphenoxy)ethenyl>-3-methyl-3-(phenylthio)-7-oxabicyclo<2.2.1>heptan-2-ol 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: 53.0%

(1E,2-endo,3-exo,6-endo)-2-(4,5-dihydro-2-furanyl)-1-<2-(4-methoxyphenoxy)ethenyl>-3-methyl-3-(phenylthio)-7-oxabicyclo<2.2.1>heptane-2,6-diol (142041-47-2,142129-68-8) + tert-butylchlorodiphenylsilane (58479-61-1) → (1E,2-endo,3-exo,6-endo)-6-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-2-(4,5-dihydro-2-furanyl)-1-<2-(4-methoxyphenoxy)ethenyl>-3-methyl-3-(phenylthio)-7-oxabicyclo<2.2.1>heptan-2-ol (142041-48-3,142184-12-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 20h; Ambient temperature;

DOI:10.1021/jo00042a036

Reference yield: 30.0%

(1Z,2-endo,3-exo,6-endo)-2-(4,5-dihydro-2-furanyl)-1-<2-(4-methoxyphenoxy)ethenyl>-3-methyl-3-(phenylthio)-7-oxabicyclo<2.2.1>heptane-2,6-diol (142041-47-2,142129-68-8) + tert-butylchlorodiphenylsilane (58479-61-1) → (1Z,2-endo,3-exo,6-endo)-6-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-2-(4,5-dihydro-2-furanyl)-1-<2-(4-methoxyphenoxy)ethenyl>-3-methyl-3-(phenylthio)-7-oxabicyclo<2.2.1>heptan-2-ol (142041-48-3,142184-12-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 16h; Ambient temperature;

DOI:10.1021/jo00042a036

Reference yield:

(1Z,3-endo,6-endo)-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-<2-(4-methoxyphenoxy)ethenyl>-3-methyl-7-oxabicyclo<2.2.1>heptan-2-one (142041-45-0,142129-65-5) → (1Z,2-endo,3-exo,6-endo)-6-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-2-(4,5-dihydro-2-furanyl)-1-<2-(4-methoxyphenoxy)ethenyl>-3-methyl-3-(phenylthio)-7-oxabicyclo<2.2.1>heptan-2-ol (142041-48-3,142184-12-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) potassium hexamethyldisilazide / 1) toluene, THF, -78 deg C, 5 min, 2) THF, -78 deg C, 1 h, then 0 deg C, 2 h

2: 1) tert-butyllithium / 1) THF, -78 deg C, 20 min, then 0 deg C, 20 min, 2) THF, TMEDA, 0 deg C, 3 h

3: 30 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

With 1H-imidazole; tert.-butyl lithium; potassium hexamethylsilazane; In N,N-dimethyl-formamide;

DOI:10.1021/jo00042a036

upstream raw materials:

(1Z,2-endo,3-exo,6-endo)-2-(4,5-dihydro-2-furanyl)-1-<2-(4-methoxyphenoxy)ethenyl>-3-methyl-3-(phenylthio)-7-oxabicyclo<2.2.1>heptane-2,6-diol

tert-butylchlorodiphenylsilane

(1Z,3-endo,6-endo)-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-<2-(4-methoxyphenoxy)ethenyl>-3-methyl-7-oxabicyclo<2.2.1>heptan-2-one

(1Z,3-exo,6-endo)-6-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-<2-(4-methoxyphenoxy)ethenyl>-3-methyl-3-(phenylthio)-7-oxabicyclo<2.2.1>heptan-2-one

Downstream raw materials:

(3aα,4α,7β,9α,10α,11aβ)-7-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-2,3,3a,4,7,8,9,10,11,11a-decahydro-4-(4-methoxyphenoxy)-10-methyl-10-(phenylthio)-6,9-epoxycyclodecafuran-11-one

(3aα,4β,7β,9α,10α,11aβ)-7-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-2,3,3a,4,7,8,9,10,11,11a-decahydro-4-(4-methoxyphenoxy)-10-methyl-10-(phenylthio)-6,9-epoxycyclodecafuran-11-one

(3α,4β,7β,9α,10α,11aα)-7-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-2,3,3a,4,7,8,9,10,11,11a-decahydro-4-(4-methoxyphenoxy)-10-methyl-10-(phenylthio)-6,9-epoxycyclodecafuran-11-one

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