9,27-Dioxabicyclo[24.1.0]heptacosa-2,6,20-triene-8,15-dione,13,14,17,19-tetrahydroxy-7,10,12,19,20,24-hexamethyl-22-methylene-, (1S,3E,7E,10S,12R,13S,14R,15E,17R,19R,24R,26S)-

Base Information

Chemical Name:9,27-Dioxabicyclo[24.1.0]heptacosa-2,6,20-triene-8,15-dione,13,14,17,19-tetrahydroxy-7,10,12,19,20,24-hexamethyl-22-methylene-, (1S,3E,7E,10S,12R,13S,14R,15E,17R,19R,24R,26S)-
CAS No.:155683-56-0
Molecular Formula:C₃₂H₅₀O₈
Molecular Weight:562.744
Hs Code.:

9,27-Dioxabicyclo[24.1.0]heptacosa-2,6,20-triene-8,15-dione,13,14,17,19-tetrahydroxy-7,10,12,19,20,24-hexamethyl-22-methylene-, (1S,3E,7E,10S,12R,13S,14R,15E,17R,19R,24R,26S)-

Synonyms:9,27-Dioxabicyclo[24.1.0]heptacosa-2,6,20-triene-8,15-dione,13,14,17,19-tetrahydroxy-7,10,12,19,20,24-hexamethyl-22-methylene-,(1S,2E,6E,10S,12R,13S,14R,17R,19R,20E,24R,26S)- (9CI); 9,27-Dioxabicyclo[24.1.0]heptacosa-2,6,20-triene-8,15-dione,13,14,17,19-tetrahydroxy-7,10,12,19,20,24-hexamethyl-22-methylene-,[1S-(1R*,2E,6E,10R*,12S*,13R*,14S*,17S*,19S*,20E,24S*,26R*)]-; Amphidinolide B2

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Chemical Property of 9,27-Dioxabicyclo[24.1.0]heptacosa-2,6,20-triene-8,15-dione,13,14,17,19-tetrahydroxy-7,10,12,19,20,24-hexamethyl-22-methylene-, (1S,3E,7E,10S,12R,13S,14R,15E,17R,19R,24R,26S)-

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Technology Process of 9,27-Dioxabicyclo[24.1.0]heptacosa-2,6,20-triene-8,15-dione,13,14,17,19-tetrahydroxy-7,10,12,19,20,24-hexamethyl-22-methylene-, (1S,3E,7E,10S,12R,13S,14R,15E,17R,19R,24R,26S)-

There total 38 articles about 9,27-Dioxabicyclo[24.1.0]heptacosa-2,6,20-triene-8,15-dione,13,14,17,19-tetrahydroxy-7,10,12,19,20,24-hexamethyl-22-methylene-, (1S,3E,7E,10S,12R,13S,14R,15E,17R,19R,24R,26S)- 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: 68.0%

: 1033588-21-4
C₃₈H₅₅NO₁₀Se

: 155683-56-0
C₃₂H₅₀O₈

Guidance literature:: With bis-trimethylsilanyl peroxide; sodium hydrogencarbonate; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1021/ja803012n

Reference yield:

: C₂₉H₄₈O₅Si

: 155683-56-0
C₃₂H₅₀O₈

Guidance literature:: Multi-step reaction with 12 steps

1.1: water; sodium periodate / tetrahydrofuran; diethyl ether / 2 h / 20 °C

2.1: lithium diisopropyl amide / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

2.2: -78 - -40 °C / Inert atmosphere

2.3: 0.5 h / -40 °C / Inert atmosphere

3.1: dmap / dichloromethane / 3 h / 20 °C / Inert atmosphere

4.1: water; acetic acid / tetrahydrofuran / 5 h / -20 °C

5.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 12 h / 20 °C / Inert atmosphere

5.2: 19 h / 20 °C / Inert atmosphere

6.1: methanol; barium hydroxide octahydrate / 0.33 h / 20 °C

7.1: tetrapropylammonium perruthennate / dichloromethane / 0.5 h / 20 °C

7.2: 24 h / 20 °C

8.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran; dichloromethane; toluene / 0.75 h / -20 °C / Inert atmosphere

9.1: titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane; decane / 5 h / -20 °C / Molecular sieve; Inert atmosphere

10.1: tributylphosphine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere

11.1: tris(dimethylamino)sulfonium trimethylsilyldifluoride; water / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 0 - 20 °C

12.1: sodium hydrogencarbonate; bis-trimethylsilanyl peroxide / dichloromethane / 1.5 h / 20 °C

With titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; dmap; sodium periodate; tetrapropylammonium perruthennate; barium hydroxide octahydrate; tributylphosphine; bis-trimethylsilanyl peroxide; dimethylsulfide borane complex; 2,4,6-trichlorobenzoyl chloride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; water; sodium hydrogencarbonate; acetic acid; triethylamine; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; decane; dichloromethane; N,N-dimethyl-formamide; toluene; 9.1: |Sharpless Asymmetric Epoxidation;
DOI:10.1021/jo3026077

Reference yield:

: 1033588-06-5
C₂₂H₄₀O₄Si

: 155683-56-0
C₃₂H₅₀O₈

Guidance literature:: Multi-step reaction with 11 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

1.2: -78 - -40 °C / Inert atmosphere

1.3: 0.5 h / -40 °C / Inert atmosphere

2.1: dmap / dichloromethane / 3 h / 20 °C / Inert atmosphere

3.1: water; acetic acid / tetrahydrofuran / 5 h / -20 °C

4.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 12 h / 20 °C / Inert atmosphere

4.2: 19 h / 20 °C / Inert atmosphere

5.1: methanol; barium hydroxide octahydrate / 0.33 h / 20 °C

6.1: tetrapropylammonium perruthennate / dichloromethane / 0.5 h / 20 °C

6.2: 24 h / 20 °C

7.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran; dichloromethane; toluene / 0.75 h / -20 °C / Inert atmosphere

8.1: titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane; decane / 5 h / -20 °C / Molecular sieve; Inert atmosphere

9.1: tributylphosphine / tetrahydrofuran / 5 h / 20 °C / Inert atmosphere

10.1: tris(dimethylamino)sulfonium trimethylsilyldifluoride; water / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 0 - 20 °C

11.1: sodium hydrogencarbonate; bis-trimethylsilanyl peroxide / dichloromethane / 1.5 h / 20 °C

With titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; dmap; tetrapropylammonium perruthennate; barium hydroxide octahydrate; tributylphosphine; bis-trimethylsilanyl peroxide; dimethylsulfide borane complex; 2,4,6-trichlorobenzoyl chloride; tris(dimethylamino)sulfonium trimethylsilyldifluoride; water; sodium hydrogencarbonate; acetic acid; triethylamine; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; lithium diisopropyl amide; In tetrahydrofuran; decane; dichloromethane; N,N-dimethyl-formamide; toluene; 8.1: |Sharpless Asymmetric Epoxidation;
DOI:10.1021/jo3026077