<3aS-<3aα,4α,7aα,7α(3E,2S^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-α(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-7-ethanol<<(1,1-dimethylethyl)dimethylsilyl>oxy>acetate

Base Information

• Chemical Name: <3aS-<3aα,4α,7aα,7α(3E,2S^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-α(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-7-ethanol<<(1,1-dimethylethyl)dimethylsilyl>oxy>acetate
• CAS No.: 115118-87-1
• Molecular Formula: C₃₉H₆₀O₇Si₂
• Molecular Weight: 697.072
• Mol file: 115118-87-1.mol

Synonyms:<3aS-<3aα,4α,7aα,7α(3E,2S^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-α(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-7-ethanol<<(1,1-dimethylethyl)dimethylsilyl>oxy>acetate

Chemical Property of <3aS-<3aα,4α,7aα,7α(3E,2S^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-α(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-7-ethanol<<(1,1-dimethylethyl)dimethylsilyl>oxy>acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3aS-<3aα,4α,7aα,7α(3E,2S^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-α(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-7-ethanol<<(1,1-dimethylethyl)dimethylsilyl>oxy>acetate

There total 17 articles about <3aS-<3aα,4α,7aα,7α(3E,2S^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-α(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-7-ethanol<<(1,1-dimethylethyl)dimethylsilyl>oxy>acetate 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: 81.0%

{[tert-butyl(dimethyl)silyl]oxy}acetic acid (105459-05-0) + <3aS-<3aα,4α,7aα,7α(3E,2S*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-α-(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-7-ethanol (107148-26-5) → <3aS-<3aα,4α,7aα,7α(3E,2S*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-α(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-7-ethanol<<(1,1-dimethylethyl)dimethylsilyl>oxy>acetate (115118-87-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; Ambient temperature;

DOI:10.1021/jo00253a021

Reference yield:

2-<(tert-butyldimethylsilyl)oxy>acetic acid benzyl ester (115118-86-0) → <3aS-<3aα,4α,7aα,7α(3E,2S*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-α(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-7-ethanol<<(1,1-dimethylethyl)dimethylsilyl>oxy>acetate (115118-87-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / H₂ / 10percent Pd/C / ethyl acetate / 3 h

2: 81 percent / dicyclohexylcarbodiimide (DCC), (dimethylamino)pyridine (DMAP) / CH₂Cl₂ / Ambient temperature

With dmap; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1021/jo00253a021

Reference yield:

(5S-cis)-5,6-dihydro-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-ol (107148-23-2) → <3aS-<3aα,4α,7aα,7α(3E,2S*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-α(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-7-ethanol<<(1,1-dimethylethyl)dimethylsilyl>oxy>acetate (115118-87-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / xylene

2: 90 percent / OsO₄, NMO

3: 90 percent / p-TsOH

4: 80 percent / DIBAL / -78 °C

5: ZnBr₂ / tetrahydrofuran / -78 °C

6: 81 percent / DCC, DMPA

With osmium(VIII) oxide; N-methyl-2-indolinone; 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; diisobutylaluminium hydride; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; zinc dibromide; In tetrahydrofuran; xylene;

DOI:10.1021/jo00383a046

upstream raw materials:

{[tert-butyl(dimethyl)silyl]oxy}acetic acid

<3aS-<3aα,4α,7aα,7α(3E,2S^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-α-(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-7-ethanol

(5S-cis)-5,6-dihydro-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-ol

<3aR-(3aα,4α,7α,7aα)>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-acetaldehyde

Downstream raw materials:

(E)-(2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-6-{(3aS,4S,7S,7aR)-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-3-methyl-hex-4-en-1-ol

(3aS,4S,7S,7aR)-7-[(E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-6-iodo-4-methyl-hex-2-enyl]-4-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

<3aS-<3aα,4α,7aα,7α(2E,4S^*,5R^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-7-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-4-methyl-2-hexenyl>-4H-1,3-dioxolo<4,5-c>pyran

<3aS-<3aα,4α,7aα,7α(3E,2R^*)>>-6-oxy>ethyl>-4H-1,3-dioxolo<4,5-c>pyran-7-yl>-2-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methyl-4-hexenoic acid methyl ester