[6-(6-{5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-4-oxo-1-triethylsilanyloxy-hex-2-enyl)-7,8-bis-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid methyl ester

Base Information

• Chemical Name: [6-(6-{5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-4-oxo-1-triethylsilanyloxy-hex-2-enyl)-7,8-bis-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid methyl ester
• CAS No.: 870700-32-6
• Molecular Formula: C₅₈H₉₆O₁₀Si₄
• Molecular Weight: 1065.74

Synonyms:[6-(6-{5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-4-oxo-1-triethylsilanyloxy-hex-2-enyl)-7,8-bis-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid methyl ester

Chemical Property of [6-(6-{5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-4-oxo-1-triethylsilanyloxy-hex-2-enyl)-7,8-bis-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of [6-(6-{5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-4-oxo-1-triethylsilanyloxy-hex-2-enyl)-7,8-bis-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid methyl ester

There total 22 articles about [6-(6-{5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-4-oxo-1-triethylsilanyloxy-hex-2-enyl)-7,8-bis-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid methyl ester 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:

(1S,2S)-1-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-2-[(4R,5S)-2,2-diethyl-5-((S)-1-hydroxy-allyl)-[1,3]dioxolan-4-yl]-ethane-1,2-diol (870700-52-0) → [6-(6-{5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-4-oxo-1-triethylsilanyloxy-hex-2-enyl)-7,8-bis-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid methyl ester (870700-32-6)

Guidance literature:

Multi-step reaction with 14 steps

1.1: ozone / CH₂Cl₂ / -78 °C

1.2: triphenylphosphine / CH₂Cl₂ / 0.58 h / -78 - 20 °C

2.1: 0.956 g / pyridine / 20 °C

3.1: 70 percent / BF₃*OEt₂ / acetonitrile / 4.5 h / 0 - 20 °C

4.1: 83 percent / benzyltrimethylammonium methoxide / benzene; methanol / 5 - 20 °C

5.1: 4-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH₂Cl₂ / 5 h / 20 °C

6.1: 0.4024 g / zinc borohydride / pentane; diethyl ether / 0.17 h / 0 °C

7.1: 98 percent / imidazole / dimethylformamide / 20 °C

8.1: 90 percent / FeCl₃*5H₂O/silica gel / CHCl₃ / 20 °C

9.1: 94 percent / toluene / 20 °C

10.1: 87 percent / P(OMe)3 / 16 h / Heating

11.1: 70 percent / DOWEX 50WX₄-400 resin; H₂O / methanol / 6 h / Heating

12.1: 100 percent / imidazole / dimethylformamide / 20 °C

13.1: ozone / CH₂Cl₂ / 0.08 h / -78 °C

13.2: triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

14.1: KHMDS / 1,2-dimethoxy-ethane / 0.5 h / 0 °C

14.2: 1,2-dimethoxy-ethane / 10 h / Heating

With pyridine; 1H-imidazole; DOWEX 50WX₄-400 resin; zinc borohydride; boron trifluoride diethyl etherate; water; silica gel; iron(III) chloride; potassium hexamethylsilazane; benzyltrismethylammonium methoxide; ozone; 4-methylmorpholine N-oxide; phosphorous acid trimethyl ester; tetrapropylammonium perruthennate; In methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; acetonitrile; pentane; benzene; 4.1: Michael addition / 14.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/jo051479m

Reference yield:

(3aR,4S,7R,7aS)-4-[(R)-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2,2-diethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6,7-diol → [6-(6-{5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-4-oxo-1-triethylsilanyloxy-hex-2-enyl)-7,8-bis-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid methyl ester (870700-32-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 0.956 g / pyridine / 20 °C

2.1: 70 percent / BF₃*OEt₂ / acetonitrile / 4.5 h / 0 - 20 °C

3.1: 83 percent / benzyltrimethylammonium methoxide / benzene; methanol / 5 - 20 °C

4.1: 4-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH₂Cl₂ / 5 h / 20 °C

5.1: 0.4024 g / zinc borohydride / pentane; diethyl ether / 0.17 h / 0 °C

6.1: 98 percent / imidazole / dimethylformamide / 20 °C

7.1: 90 percent / FeCl₃*5H₂O/silica gel / CHCl₃ / 20 °C

8.1: 94 percent / toluene / 20 °C

9.1: 87 percent / P(OMe)3 / 16 h / Heating

10.1: 70 percent / DOWEX 50WX₄-400 resin; H₂O / methanol / 6 h / Heating

11.1: 100 percent / imidazole / dimethylformamide / 20 °C

12.1: ozone / CH₂Cl₂ / 0.08 h / -78 °C

12.2: triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

13.1: KHMDS / 1,2-dimethoxy-ethane / 0.5 h / 0 °C

13.2: 1,2-dimethoxy-ethane / 10 h / Heating

With pyridine; 1H-imidazole; DOWEX 50WX₄-400 resin; zinc borohydride; boron trifluoride diethyl etherate; water; silica gel; iron(III) chloride; potassium hexamethylsilazane; benzyltrismethylammonium methoxide; ozone; 4-methylmorpholine N-oxide; phosphorous acid trimethyl ester; tetrapropylammonium perruthennate; In methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; acetonitrile; pentane; benzene; 3.1: Michael addition / 13.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/jo051479m

Reference yield:

(4R,5R)-5-[(1R,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-2-((R)-2,2-diethyl-[1,3]dioxolan-4-yl)-1-hydroxy-ethyl]-2,2-diethyl-[1,3]dioxolane-4-carbaldehyde → [6-(6-{5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-4-oxo-1-triethylsilanyloxy-hex-2-enyl)-7,8-bis-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid methyl ester (870700-32-6)

Guidance literature:

Multi-step reaction with 16 steps

1.1: tetrahydrofuran / 12.5 h / 0 - 20 °C

2.1: 3.80 g / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C

3.1: ozone / CH₂Cl₂ / -78 °C

3.2: triphenylphosphine / CH₂Cl₂ / 0.58 h / -78 - 20 °C

4.1: 0.956 g / pyridine / 20 °C

5.1: 70 percent / BF₃*OEt₂ / acetonitrile / 4.5 h / 0 - 20 °C

6.1: 83 percent / benzyltrimethylammonium methoxide / benzene; methanol / 5 - 20 °C

7.1: 4-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH₂Cl₂ / 5 h / 20 °C

8.1: 0.4024 g / zinc borohydride / pentane; diethyl ether / 0.17 h / 0 °C

9.1: 98 percent / imidazole / dimethylformamide / 20 °C

10.1: 90 percent / FeCl₃*5H₂O/silica gel / CHCl₃ / 20 °C

11.1: 94 percent / toluene / 20 °C

12.1: 87 percent / P(OMe)3 / 16 h / Heating

13.1: 70 percent / DOWEX 50WX₄-400 resin; H₂O / methanol / 6 h / Heating

14.1: 100 percent / imidazole / dimethylformamide / 20 °C

15.1: ozone / CH₂Cl₂ / 0.08 h / -78 °C

15.2: triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

16.1: KHMDS / 1,2-dimethoxy-ethane / 0.5 h / 0 °C

16.2: 1,2-dimethoxy-ethane / 10 h / Heating

With pyridine; 1H-imidazole; DOWEX 50WX₄-400 resin; zinc borohydride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; silica gel; iron(III) chloride; potassium hexamethylsilazane; benzyltrismethylammonium methoxide; ozone; 4-methylmorpholine N-oxide; phosphorous acid trimethyl ester; tetrapropylammonium perruthennate; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; acetonitrile; pentane; benzene; 6.1: Michael addition / 16.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/jo051479m

upstream raw materials:

(4-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-2-oxo-butyl)-phosphonic acid dimethyl ester

[(2R,4aS,6R,7R,8S,8aS)-6-((R)-2-Oxo-1-triethylsilanyloxy-ethyl)-7,8-bis-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid methyl ester

[(2R,4aS,6S,7S,8R,8aR)-7,8-Dihydroxy-6-((S)-1-hydroxy-allyl)-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid methyl ester

(1S,2S)-1-((R)-2,2-Diethyl-[1,3]dioxolan-4-yl)-2-[(4R,5S)-2,2-diethyl-5-((S)-1-hydroxy-allyl)-[1,3]dioxolan-4-yl]-ethane-1,2-diol

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