(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(3aR,4R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]-1-phenyl-ethanol

Base Information

• Chemical Name: (R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(3aR,4R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]-1-phenyl-ethanol
• CAS No.: 864444-88-2
• Molecular Formula: C₂₉H₅₂O₆Si₂
• Molecular Weight: 552.899

Synonyms:(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(3aR,4R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]-1-phenyl-ethanol

Chemical Property of (R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(3aR,4R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]-1-phenyl-ethanol

Chemical Property:

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Technology Process of (R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(3aR,4R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]-1-phenyl-ethanol

There total 5 articles about (R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(3aR,4R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]-1-phenyl-ethanol 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: 93.0%

(R)-1-((3aR,4R,6S,7S,7aS)-7-Hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-1-phenyl-ethane-1,2-diol (864444-85-9) + tert-butyldimethylsilyl chloride (18162-48-6) → (R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(3aR,4R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]-1-phenyl-ethanol (864444-88-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1021/ol050975u

Reference yield:

tributyl-(2,2,4-trimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)-stannane → (R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(3aR,4R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]-1-phenyl-ethanol (864444-88-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 66 percent / CsF / Pd(PPh₃)4; CuI / dimethylformamide / 24 h / 45 °C

2.1: 49 percent / AD-mix α / 2-methyl-propan-2-ol; H2O / 24 h / 20 °C

3.1: BH₃*THF / tetrahydrofuran / 27 h / 0 - 20 °C

3.2: 75 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 0 - 20 °C

4.1: 93 percent / imidazole / dimethylformamide / 24 h / 20 °C

With 1H-imidazole; AD-mix-α; borane-THF; cesium fluoride; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Stille cross-coupling;

DOI:10.1021/ol050975u

Reference yield:

1-phenyl-1-iodoethylene (51246-20-9) → (R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(3aR,4R,6S,7S,7aR)-7-(tert-butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]-1-phenyl-ethanol (864444-88-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 66 percent / CsF / Pd(PPh₃)4; CuI / dimethylformamide / 24 h / 45 °C

2.1: 49 percent / AD-mix α / 2-methyl-propan-2-ol; H2O / 24 h / 20 °C

3.1: BH₃*THF / tetrahydrofuran / 27 h / 0 - 20 °C

3.2: 75 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 0 - 20 °C

4.1: 93 percent / imidazole / dimethylformamide / 24 h / 20 °C

With 1H-imidazole; AD-mix-α; borane-THF; cesium fluoride; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Stille cross-coupling;

DOI:10.1021/ol050975u

upstream raw materials:

(R)-1-((3aR,4R,6S,7S,7aS)-7-Hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl)-1-phenyl-ethane-1,2-diol

tert-butyldimethylsilyl chloride

2,2,4-trimethyl-6-(1-phenyl-vinyl)-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran

(R)-1-Phenyl-1-((3aR,4R,7aS)-2,2,4-trimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran-6-yl)-ethane-1,2-diol

Downstream raw materials:

(2S)-methyl 3,7-anhydro-2-phenyl-5-O-methyl-8-deoxy-α-D-altro-octitolate

(S)-[(3aR,4R,6S,7S,7aR)-7-(tert-Butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]-hydroxy-phenyl-acetic acid methyl ester

(S)-[(2S,3S,4R,5S,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-4,5-dihydroxy-6-methyl-tetrahydro-pyran-2-yl]-hydroxy-phenyl-acetic acid methyl ester

(S)-[(3aR,4R,6S,7S,7aR)-7-(tert-Butyl-dimethyl-silanyloxy)-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]-hydroxy-phenyl-acetaldehyde

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