<3aS-<3aα,4α,7aα,7α(2Z,4S^*,5R^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-7-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-methyl-2-hexenyl>-4H-1,3-dioxolo<4,5-c>pyran

Base Information

• Chemical Name: <3aS-<3aα,4α,7aα,7α(2Z,4S^*,5R^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-7-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-methyl-2-hexenyl>-4H-1,3-dioxolo<4,5-c>pyran
• CAS No.: 115183-66-9
• Molecular Formula: C₃₉H₆₂O₅Si₂
• Molecular Weight: 667.089

Synonyms:

Chemical Property of <3aS-<3aα,4α,7aα,7α(2Z,4S^*,5R^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-7-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-methyl-2-hexenyl>-4H-1,3-dioxolo<4,5-c>pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3aS-<3aα,4α,7aα,7α(2Z,4S^*,5R^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-7-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-methyl-2-hexenyl>-4H-1,3-dioxolo<4,5-c>pyran

There total 17 articles about <3aS-<3aα,4α,7aα,7α(2Z,4S^*,5R^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-7-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-methyl-2-hexenyl>-4H-1,3-dioxolo<4,5-c>pyran 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:

(+)-(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl butanol (85576-59-6) → <3aS-<3aα,4α,7aα,7α(2Z,4S*,5R*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-7-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-methyl-2-hexenyl>-4H-1,3-dioxolo<4,5-c>pyran (115183-66-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / pyridine / Ambient temperature

2: 90 percent / NaI / butan-2-one / 1.5 h / Heating

3: 81 percent / hexamethylphosphoric acid triamide / 0.5 h / Ambient temperature

With pyridine; sodium iodide; In N,N,N,N,N,N-hexamethylphosphoric triamide; butanone;

DOI:10.1021/jo00253a021

Reference yield:

(2S,3S)-2-(2-Hydroxy-ethyl)-3,6-dihydro-2H-pyran-3-ol → <3aS-<3aα,4α,7aα,7α(2Z,4S*,5R*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-7-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-methyl-2-hexenyl>-4H-1,3-dioxolo<4,5-c>pyran (115183-66-9)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / 2 h / 0 - 20 °C

2: 100 percent / xylene / 12 h / Heating

3: 90 percent / N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O / 24 h / Ambient temperature

4: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature

5: 74 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.5 h / -90 °C

With pyridine; osmium(VIII) oxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; copper(II) sulfate; 4-methylmorpholine N-oxide; In diethyl ether; hexane; water; acetone; xylene;

DOI:10.1021/jo00253a021

Reference yield:

2-{(3S,4R,5R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,5-dihydroxy-tetrahydro-pyran-3-yl}-N,N-dimethyl-acetamide (115118-80-4) → <3aS-<3aα,4α,7aα,7α(2Z,4S*,5R*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-7-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-methyl-2-hexenyl>-4H-1,3-dioxolo<4,5-c>pyran (115183-66-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / cupric sulfate, p-toluenesulfonic acid / 24 h / Ambient temperature

2: 74 percent / diisobutylaluminium hydride / diethyl ether; hexane / 0.5 h / -90 °C

With diisobutylaluminium hydride; toluene-4-sulfonic acid; copper(II) sulfate; In diethyl ether; hexane;

DOI:10.1021/jo00253a021

upstream raw materials:

(2S,3S)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methyl-1-(phenylsulfonyl)butane

<3aR-(3aα,4α,7α,7aα)>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetaldehyde

(+)-(2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl butanol

2-{(3S,4R,5R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,5-dihydroxy-tetrahydro-pyran-3-yl}-N,N-dimethyl-acetamide

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