3-ethyl 1,2-dimethyl (1S,2S,3R,4R,5R,10R,11R)-10-benzyloxy-4,5-(diethylmethylenedioxy)-1,2-(dimethylmethylenedioxy)-11-methyl-6-oxo-12-phenyl-3-(trimethylsilyloxy)dodecane-1,2,3-tricarboxylate

Base Information

• Chemical Name: 3-ethyl 1,2-dimethyl (1S,2S,3R,4R,5R,10R,11R)-10-benzyloxy-4,5-(diethylmethylenedioxy)-1,2-(dimethylmethylenedioxy)-11-methyl-6-oxo-12-phenyl-3-(trimethylsilyloxy)dodecane-1,2,3-tricarboxylate
• CAS No.: 191935-33-8
• Molecular Formula: C₄₄H₆₄O₁₃Si
• Molecular Weight: 829.07
• Mol file: 191935-33-8.mol

Synonyms:3-ethyl 1,2-dimethyl (1S,2S,3R,4R,5R,10R,11R)-10-benzyloxy-4,5-(diethylmethylenedioxy)-1,2-(dimethylmethylenedioxy)-11-methyl-6-oxo-12-phenyl-3-(trimethylsilyloxy)dodecane-1,2,3-tricarboxylate

Chemical Property of 3-ethyl 1,2-dimethyl (1S,2S,3R,4R,5R,10R,11R)-10-benzyloxy-4,5-(diethylmethylenedioxy)-1,2-(dimethylmethylenedioxy)-11-methyl-6-oxo-12-phenyl-3-(trimethylsilyloxy)dodecane-1,2,3-tricarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-ethyl 1,2-dimethyl (1S,2S,3R,4R,5R,10R,11R)-10-benzyloxy-4,5-(diethylmethylenedioxy)-1,2-(dimethylmethylenedioxy)-11-methyl-6-oxo-12-phenyl-3-(trimethylsilyloxy)dodecane-1,2,3-tricarboxylate

There total 32 articles about 3-ethyl 1,2-dimethyl (1S,2S,3R,4R,5R,10R,11R)-10-benzyloxy-4,5-(diethylmethylenedioxy)-1,2-(dimethylmethylenedioxy)-11-methyl-6-oxo-12-phenyl-3-(trimethylsilyloxy)dodecane-1,2,3-tricarboxylate 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%

3-ethyl 1,2-dimethyl (1S,2S,3R,4R,5R,10R,11R)-10-benzyloxy-4,5-(diethylmethylenedioxy)-1,2-(dimethylmethylenedioxy)-11-methyl-6-oxo-12-phenyl-3-(trimethylsilyloxy)-7-dodecyne-1,2,3-tricarboxylate (191935-32-7) → 3-ethyl 1,2-dimethyl (1S,2S,3R,4R,5R,10R,11R)-10-benzyloxy-4,5-(diethylmethylenedioxy)-1,2-(dimethylmethylenedioxy)-11-methyl-6-oxo-12-phenyl-3-(trimethylsilyloxy)dodecane-1,2,3-tricarboxylate (191935-33-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 0.166667h; under 760 Torr;

DOI:10.1016/j.tet.2005.09.030

Reference yield:

4-O-benzyl-2,3-O-isopropylidene-D-threose (81801-09-4) → 3-ethyl 1,2-dimethyl (1S,2S,3R,4R,5R,10R,11R)-10-benzyloxy-4,5-(diethylmethylenedioxy)-1,2-(dimethylmethylenedioxy)-11-methyl-6-oxo-12-phenyl-3-(trimethylsilyloxy)dodecane-1,2,3-tricarboxylate (191935-33-8)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 95 percent / 2-methyl-2-butene; NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 18 h / 20 °C

2.1: oxalyl chloride; DMF / CH₂Cl₂ / 1.5 h / 20 °C

3.1: 77 percent / n-Bu₄NI / CH₂Cl₂; H₂O / 0.17 h / 0 °C

4.1: butyllithium; 1,1,1,3,3,3-hexamethyldisilazane / hexane; tetrahydrofuran / 0.5 h / -78 °C

4.2: 95 percent / tetrahydrofuran; hexane / -78 - 20 °C

5.1: 32 percent / Sn(OTf)2 / various solvent(s) / 1.5 h / -70 °C

6.1: 23 percent / KHMDS / toluene; tetrahydrofuran / -78 - -23 °C

7.1: 87 percent / Hg(OCOCF₃)2 / methanol / 10 h / Heating

8.1: 2.47 g / hydrogen / palladium hydroxide on carbon / ethyl acetate / 10 h / 760 Torr

9.1: 2.14 g / Dess-Martin periodinane / CH₂Cl₂ / 8 h / 20 °C

10.1: 2.31 g / NaH₂PO₄; 2-methyl-2-butene; NaClO₂ / H₂O; 2-methyl-propan-2-ol / 2.5 h / 20 °C

11.1: 1.81 g / diethyl ether / 0.17 h / 0 °C

12.1: 94 percent / sodium iodide; chlorotrimethylsilane / acetonitrile / 2 h / -23 °C

13.1: 1.42 g / 3 h / 90 °C

14.1: 87 percent / HCl / diethyl ether; H₂O / 1.5 h / 20 °C

15.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 3.5 h / 20 °C

16.1: butyllithium / hexane; tetrahydrofuran / 0.75 h / -78 °C

16.2: 97 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

17.1: 82 percent / Dess-Martin periodinane / CH₂Cl₂ / 11 h / 20 °C

18.1: 93 percent / hydrogen / palladium on carbon / ethyl acetate / 0.17 h / 760 Torr

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; n-butyllithium; chloro-trimethyl-silane; 2-methyl-but-2-ene; oxalyl dichloride; hydrogen; mercury(II) trifluoroacetate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; Dess-Martin periodane; N,N-dimethyl-formamide; 1,1,1,3,3,3-hexamethyl-disilazane; sodium iodide; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; toluene; acetonitrile; tert-butyl alcohol; 6.1: aldol coupling;

DOI:10.1016/j.tet.2005.09.030

Reference yield:

S-methyl (2S,3R)-4-benzyloxy-2,3-(dimethylmethylenedioxy)butanethioate (871514-33-9) → 3-ethyl 1,2-dimethyl (1S,2S,3R,4R,5R,10R,11R)-10-benzyloxy-4,5-(diethylmethylenedioxy)-1,2-(dimethylmethylenedioxy)-11-methyl-6-oxo-12-phenyl-3-(trimethylsilyloxy)dodecane-1,2,3-tricarboxylate (191935-33-8)

Guidance literature:

Multi-step reaction with 15 steps

1.1: butyllithium; 1,1,1,3,3,3-hexamethyldisilazane / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: 95 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 32 percent / Sn(OTf)2 / various solvent(s) / 1.5 h / -70 °C

3.1: 23 percent / KHMDS / toluene; tetrahydrofuran / -78 - -23 °C

4.1: 87 percent / Hg(OCOCF₃)2 / methanol / 10 h / Heating

5.1: 2.47 g / hydrogen / palladium hydroxide on carbon / ethyl acetate / 10 h / 760 Torr

6.1: 2.14 g / Dess-Martin periodinane / CH₂Cl₂ / 8 h / 20 °C

7.1: 2.31 g / NaH₂PO₄; 2-methyl-2-butene; NaClO₂ / H₂O; 2-methyl-propan-2-ol / 2.5 h / 20 °C

8.1: 1.81 g / diethyl ether / 0.17 h / 0 °C

9.1: 94 percent / sodium iodide; chlorotrimethylsilane / acetonitrile / 2 h / -23 °C

10.1: 1.42 g / 3 h / 90 °C

11.1: 87 percent / HCl / diethyl ether; H₂O / 1.5 h / 20 °C

12.1: 91 percent / Dess-Martin periodinane / CH₂Cl₂ / 3.5 h / 20 °C

13.1: butyllithium / hexane; tetrahydrofuran / 0.75 h / -78 °C

13.2: 97 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

14.1: 82 percent / Dess-Martin periodinane / CH₂Cl₂ / 11 h / 20 °C

15.1: 93 percent / hydrogen / palladium on carbon / ethyl acetate / 0.17 h / 760 Torr

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; n-butyllithium; chloro-trimethyl-silane; 2-methyl-but-2-ene; hydrogen; mercury(II) trifluoroacetate; potassium hexamethylsilazane; Dess-Martin periodane; 1,1,1,3,3,3-hexamethyl-disilazane; sodium iodide; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; toluene; acetonitrile; tert-butyl alcohol; 3.1: aldol coupling;

DOI:10.1016/j.tet.2005.09.030

upstream raw materials:

3-ethyl 1,2-dimethyl (1S,2S,3R,4R,5R,10R,11R)-10-benzyloxy-4,5-(diethylmethylenedioxy)-1,2-(dimethylmethylenedioxy)-11-methyl-6-oxo-12-phenyl-3-(trimethylsilyloxy)-7-dodecyne-1,2,3-tricarboxylate

(4R,5S)-2,2-Diethyl-5-(2-methoxy-ethoxymethoxymethyl)-[1,3]dioxolane-4-carbaldehyde

(2S,3S)-2,3-diethylmethylenedioxy-4-[(2-methoxyethoxy)methoxy]-1-butanol

(2R,3S)-2,3-diethylmethylenedioxy-4-[(2-methoxyethoxy)methoxy]butyric acid

Downstream raw materials:

5-ethyl 3,4-dimethyl [1S,1(4R,5R),3S,4S,5R,6R,7R]-1-(4-benzyloxy-5-methyl-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,7R]-1-(4-benzyloxy-5-methyl-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,7R]-4,6,7-trihydroxy-1-(4-hydroxy-5-methyl-6-phenylhexyl)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,6(4E,6R),7R]-1-(4-acetoxy-5-methyl-6-phenylhexyl)-7-(tert-butoxycarbonyloxy)-4-hydroxy-6-(6-methyl-9-phenyl-4-nonenoyl)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate