(S)-9-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-hydroxy-8-methyl-3-((R)-toluene-4-sulfinyl)-nonan-4-one

Base Information

• Chemical Name: (S)-9-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-hydroxy-8-methyl-3-((R)-toluene-4-sulfinyl)-nonan-4-one
• CAS No.: 880344-52-5
• Molecular Formula: C₄₉H₇₄O₈SSi₂
• Molecular Weight: 879.359

Synonyms:(S)-9-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-hydroxy-8-methyl-3-((R)-toluene-4-sulfinyl)-nonan-4-one

Chemical Property of (S)-9-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-hydroxy-8-methyl-3-((R)-toluene-4-sulfinyl)-nonan-4-one

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Technology Process of (S)-9-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-hydroxy-8-methyl-3-((R)-toluene-4-sulfinyl)-nonan-4-one

There total 18 articles about (S)-9-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-hydroxy-8-methyl-3-((R)-toluene-4-sulfinyl)-nonan-4-one 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: 87.0%

(S)-2,2-Dimethyl-4-[3-((R)-toluene-4-sulfinyl)-propyl]-[1,3]dioxolane (82430-64-6) + 5-{(S)-2-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl}-dihydro-furan-2-one (392663-13-7) → (S)-9-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-hydroxy-8-methyl-3-((R)-toluene-4-sulfinyl)-nonan-4-one (880344-52-5)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.25h;

DOI:10.1002/1521-3773(20011105)40

Reference yield:

(4R)-4,5-isopropylidenedioxy-1-(dimethoxyphosphoryl)-2-pentanone (157240-43-2) → (S)-9-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-hydroxy-8-methyl-3-((R)-toluene-4-sulfinyl)-nonan-4-one (880344-52-5)

Guidance literature:

Multi-step reaction with 13 steps

1.1: LiCl; N,N-diisopropylethylamine / acetonitrile / 2 h / 25 °C

1.2: 86 percent / acetonitrile / 15 h / 25 °C

2.1: 98 percent / LiI; LiAlH₄ / diethyl ether / -100 - 0 °C

3.1: 97 percent / AcOH / H₂O / 5 h / 40 °C

4.1: 70 percent / NaHCO₃; N-iodosuccinimide / tetrahydrofuran / 36 h / 0 °C

5.1: 99 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 10 h / 25 °C

6.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

7.1: 99 percent / H₂; Raney-Ni catalyst / ethanol / 1 h / 25 °C

8.1: 88 percent / H₂ / Pd(OH)2/C / ethanol / 3 h / 25 °C

9.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 - 25 °C

10.1: Mg / tetrahydrofuran / 2 h / 25 °C

10.2: tetrahydrofuran / 2 h / -78 - 0 °C

11.1: N-methylmorpholine-N-oxide; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 12 h / 25 °C

11.2: NaIO₄; saline solution buffer / 2-methyl-propan-2-ol; tetrahydrofuran / 5 h / 25 °C / pH 7

12.1: N-idosuccinimide; tetra-n-butylammonium iodide / CH₂Cl₂ / 1 h / 25 °C

13.1: lithium diisopropylamide / tetrahydrofuran / 0.42 h / -78 °C

13.2: tetrahydrofuran / 0.67 h / -78 - 0 °C

With 2,6-dimethylpyridine; dmap; N-iodo-succinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; Raney-Ni catalyst; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; Dess-Martin periodane; magnesium; acetic acid; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; lithium iodide; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja0547477

Reference yield:

(E)-(2R,4S,7S)-8-Benzyloxy-7-methyl-oct-5-ene-1,2,4-triol (392663-03-5) → (S)-9-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-7-hydroxy-8-methyl-3-((R)-toluene-4-sulfinyl)-nonan-4-one (880344-52-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 70 percent / NaHCO₃; N-iodosuccinimide / tetrahydrofuran / 36 h / 0 °C

2.1: 99 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 10 h / 25 °C

3.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 99 percent / H₂; Raney-Ni catalyst / ethanol / 1 h / 25 °C

5.1: 88 percent / H₂ / Pd(OH)2/C / ethanol / 3 h / 25 °C

6.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 - 25 °C

7.1: Mg / tetrahydrofuran / 2 h / 25 °C

7.2: tetrahydrofuran / 2 h / -78 - 0 °C

8.1: N-methylmorpholine-N-oxide; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 12 h / 25 °C

8.2: NaIO₄; saline solution buffer / 2-methyl-propan-2-ol; tetrahydrofuran / 5 h / 25 °C / pH 7

9.1: N-idosuccinimide; tetra-n-butylammonium iodide / CH₂Cl₂ / 1 h / 25 °C

10.1: lithium diisopropylamide / tetrahydrofuran / 0.42 h / -78 °C

10.2: tetrahydrofuran / 0.67 h / -78 - 0 °C

With 2,6-dimethylpyridine; dmap; N-iodo-succinimide; osmium(VIII) oxide; Raney-Ni catalyst; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; Dess-Martin periodane; magnesium; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/ja0547477

upstream raw materials:

(S)-2,2-Dimethyl-4-[3-((R)-toluene-4-sulfinyl)-propyl]-[1,3]dioxolane

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

(R)-methyl p-tolyl sulfoxide

(4S)-4-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane

Downstream raw materials:

C₄₀H₅₂O₇SSi

C₄₇H₅₆O₈SSi

(S)-1-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-9-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-7-((R)-toluene-4-sulfinyl)-nonane-3,6-dione

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