Acetic acid (2S,3S,4aS,5S,6R,8aS)-5-(tert-butyl-diphenyl-silanyloxy)-2,3-diphenyl-2,3,4a,5,6,8a-hexahydro-benzo[1,4]dioxin-6-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,4aS,5S,6R,8aS)-5-(tert-butyl-diphenyl-silanyloxy)-2,3-diphenyl-2,3,4a,5,6,8a-hexahydro-benzo[1,4]dioxin-6-yl ester
• CAS No.: 849596-48-1
• Molecular Formula: C₃₈H₄₀O₅Si
• Molecular Weight: 604.818
• Mol file: 849596-48-1.mol

Synonyms:

Chemical Property of Acetic acid (2S,3S,4aS,5S,6R,8aS)-5-(tert-butyl-diphenyl-silanyloxy)-2,3-diphenyl-2,3,4a,5,6,8a-hexahydro-benzo[1,4]dioxin-6-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3S,4aS,5S,6R,8aS)-5-(tert-butyl-diphenyl-silanyloxy)-2,3-diphenyl-2,3,4a,5,6,8a-hexahydro-benzo[1,4]dioxin-6-yl ester

There total 13 articles about Acetic acid (2S,3S,4aS,5S,6R,8aS)-5-(tert-butyl-diphenyl-silanyloxy)-2,3-diphenyl-2,3,4a,5,6,8a-hexahydro-benzo[1,4]dioxin-6-yl 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)-2-(cyclohex-2'-enyloxy)-1,2-diphenylethanol → Acetic acid (2S,3S,4aS,5S,6R,8aS)-5-(tert-butyl-diphenyl-silanyloxy)-2,3-diphenyl-2,3,4a,5,6,8a-hexahydro-benzo[1,4]dioxin-6-yl ester (849596-48-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 33 percent / AgOTf / CH₂Cl₂ / 0.5 h / -78 °C

2: 90 percent / NaIO₄; NaHCO₃ / methanol; H₂O / 48 h / 90 °C

3: 89 percent / dimethyldioxirane / acetone / 3 h / 0 °C

4: NaBH₄ / ethanol / 4 h / Heating

5: 97 mg / H₂O₂ / ethanol; tetrahydrofuran / Heating

6: 87 percent / imidazole / dimethylformamide / 14 h / 80 °C

7: 51 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 20 h / Heating

8: 83 percent / NaBH₄ / butan-1-ol / 24 h / Heating

9: 90 percent / NaIO₄; NaHCO₃ / methanol; H₂O / 48 h / 90 °C

10: 11 mg / pyridine / 2 h

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; dihydrogen peroxide; silver trifluoromethanesulfonate; 3,3-dimethyldioxirane; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; butan-1-ol;

DOI:10.1016/j.tet.2005.01.003

Reference yield:

(S,S)-hydrobenzoin (2325-10-2) → Acetic acid (2S,3S,4aS,5S,6R,8aS)-5-(tert-butyl-diphenyl-silanyloxy)-2,3-diphenyl-2,3,4a,5,6,8a-hexahydro-benzo[1,4]dioxin-6-yl ester (849596-48-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 55 percent / NaH / dimethylformamide; various solvent(s) / 1 h / 20 °C

2: 33 percent / AgOTf / CH₂Cl₂ / 0.5 h / -78 °C

3: 90 percent / NaIO₄; NaHCO₃ / methanol; H₂O / 48 h / 90 °C

4: 89 percent / dimethyldioxirane / acetone / 3 h / 0 °C

5: NaBH₄ / ethanol / 4 h / Heating

6: 97 mg / H₂O₂ / ethanol; tetrahydrofuran / Heating

7: 87 percent / imidazole / dimethylformamide / 14 h / 80 °C

8: 51 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 20 h / Heating

9: 83 percent / NaBH₄ / butan-1-ol / 24 h / Heating

10: 90 percent / NaIO₄; NaHCO₃ / methanol; H₂O / 48 h / 90 °C

11: 11 mg / pyridine / 2 h

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; dihydrogen peroxide; silver trifluoromethanesulfonate; 3,3-dimethyldioxirane; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; butan-1-ol;

DOI:10.1016/j.tet.2005.01.003

Reference yield:

rac-3-bromocyclohexene (1521-51-3,113667-32-6) → Acetic acid (2S,3S,4aS,5S,6R,8aS)-5-(tert-butyl-diphenyl-silanyloxy)-2,3-diphenyl-2,3,4a,5,6,8a-hexahydro-benzo[1,4]dioxin-6-yl ester (849596-48-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 55 percent / NaH / dimethylformamide; various solvent(s) / 1 h / 20 °C

2: 33 percent / AgOTf / CH₂Cl₂ / 0.5 h / -78 °C

3: 90 percent / NaIO₄; NaHCO₃ / methanol; H₂O / 48 h / 90 °C

4: 89 percent / dimethyldioxirane / acetone / 3 h / 0 °C

5: NaBH₄ / ethanol / 4 h / Heating

6: 97 mg / H₂O₂ / ethanol; tetrahydrofuran / Heating

7: 87 percent / imidazole / dimethylformamide / 14 h / 80 °C

8: 51 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 20 h / Heating

9: 83 percent / NaBH₄ / butan-1-ol / 24 h / Heating

10: 90 percent / NaIO₄; NaHCO₃ / methanol; H₂O / 48 h / 90 °C

11: 11 mg / pyridine / 2 h

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; dihydrogen peroxide; silver trifluoromethanesulfonate; 3,3-dimethyldioxirane; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; butan-1-ol;

DOI:10.1016/j.tet.2005.01.003

upstream raw materials:

acetic anhydride

(1S,3S,4S,6S,7S,8R)-3,4-diphenyl-2,5-dioxa-7-tert-butyldiphenylsilyloxybicyclo[4,4,0]dec-9-en-8-ol

(S,S)-hydrobenzoin

rac-3-bromocyclohexene