(S)-2-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-propane-1,2-diol

Base Information

• Chemical Name: (S)-2-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-propane-1,2-diol
• CAS No.: 90461-00-0
• Molecular Formula: C₂₆H₃₈O₄Si
• Molecular Weight: 442.671

Synonyms:(S)-2-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-propane-1,2-diol

Chemical Property of (S)-2-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-propane-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (S)-2-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-propane-1,2-diol

There total 12 articles about (S)-2-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-propane-1,2-diol 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: 95.3%

(S)-4-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-4-methyl-[1,3]dioxolan-2-one (90460-99-4) → (S)-2-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-propane-1,2-diol (90461-00-0)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 3h;

DOI:10.1021/jo00188a014

Reference yield:

Acetic acid (1E,3Z,5E)-7-hydroxy-2,6-dimethyl-hepta-1,3,5-trienyl ester → (S)-2-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-propane-1,2-diol (90461-00-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 50 percent / 1.) Ti(O-i-Pr)4, (-)-Diethyl D-tartrate, t-BuOOH, / CH₂Cl₂ / -15 °C

2: 94.7 percent / Et₃N / CH₂Cl₂ / 24 h / Ambient temperature

3: 94 percent / 5percent HClO₄ / acetonitrile / 4 h / Ambient temperature

4: 90 percent / Phosphorus oxychloride / CH₂Cl₂ / 24 h / Ambient temperature

5: 90 percent / K₂CO₃ / methanol / 1 h / 0 °C

6: 83 percent / Dowex H⁺ / methanol / 24 h / Ambient temperature

7: 60 percent / 1.) Ti(O-i-Pr), (-)-Diethyl D-tatrate, t-BuOOH, 2.) Tattratic acid / CH₂Cl₂ / 1.) -23 degC, 30 min. 2.) stirring

8: 82.5 percent / pyridine / 0 °C / overnight

9: NaI / butan-2-one / 3 h / Heating

10: 98.4 percent / Tri-n-butyltin hydride / ethanol / 2 h / Ambient temperature

11: Imidazole / dimethylformamide / 3 h / 60 °C

12: 95.3 percent / LiAlH₄ / diethyl ether / 3 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; perchloric acid; diethyl (2S,3S)-tartrate; Dowex H⁺; Tattratic acid; tri-n-butyl-tin hydride; potassium carbonate; (-)-diethyl tartrate; triethylamine; sodium iodide; trichlorophosphate; In pyridine; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; butanone;

DOI:10.1021/jo00188a014

Reference yield:

(S)-4-((E)-(R)-1,6-Dihydroxy-4-methyl-hex-4-enyl)-4-methyl-[1,3]dioxolan-2-one (90460-97-2) → (S)-2-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-propane-1,2-diol (90461-00-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 60 percent / 1.) Ti(O-i-Pr), (-)-Diethyl D-tatrate, t-BuOOH, 2.) Tattratic acid / CH₂Cl₂ / 1.) -23 degC, 30 min. 2.) stirring

2: 82.5 percent / pyridine / 0 °C / overnight

3: NaI / butan-2-one / 3 h / Heating

4: 98.4 percent / Tri-n-butyltin hydride / ethanol / 2 h / Ambient temperature

5: Imidazole / dimethylformamide / 3 h / 60 °C

6: 95.3 percent / LiAlH₄ / diethyl ether / 3 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; Tattratic acid; tri-n-butyl-tin hydride; (-)-diethyl tartrate; sodium iodide; In pyridine; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; butanone;

DOI:10.1021/jo00188a014

upstream raw materials:

(S)-4-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-4-methyl-[1,3]dioxolan-2-one

(E)-5-((2R,3R)-3-(hydroxymethyl)-3-methyloxiran-2-yl)-3-methylpent-2-en-1-yl acetate

(S)-4-((E)-(R)-1,6-Dihydroxy-4-methyl-hex-4-enyl)-4-methyl-[1,3]dioxolan-2-one

(S)-4-[(2R,5S)-5-((R)-1,2-Dihydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-4-methyl-[1,3]dioxolan-2-one

Downstream raw materials:

Toluene-4-sulfonic acid (S)-2-{(2R,5S)-5-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-2-hydroxy-propyl ester

tert-Butyl-{(R)-1-[(2S,5R)-2-methyl-5-((S)-2-methyl-oxiranyl)-tetrahydro-furan-2-yl]-ethoxy}-diphenyl-silane

(S)-2-{(2R,5S)-5-[(R)-1-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-hex-5-en-2-ol

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