(1R,6S,7S,8R)-3,4-dibromo-7-(tert-butyldiphenylsilyloxy)methyl-8-methyl-9-oxabicyclo[4.2.1]nonane

Base Information

• Chemical Name: (1R,6S,7S,8R)-3,4-dibromo-7-(tert-butyldiphenylsilyloxy)methyl-8-methyl-9-oxabicyclo[4.2.1]nonane
• CAS No.: 817201-17-5
• Molecular Formula: C₂₆H₃₄Br₂O₂Si
• Molecular Weight: 566.448
• Mol file: 817201-17-5.mol

Synonyms:(1R,6S,7S,8R)-3,4-dibromo-7-(tert-butyldiphenylsilyloxy)methyl-8-methyl-9-oxabicyclo[4.2.1]nonane

Chemical Property of (1R,6S,7S,8R)-3,4-dibromo-7-(tert-butyldiphenylsilyloxy)methyl-8-methyl-9-oxabicyclo[4.2.1]nonane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,6S,7S,8R)-3,4-dibromo-7-(tert-butyldiphenylsilyloxy)methyl-8-methyl-9-oxabicyclo[4.2.1]nonane

There total 19 articles about (1R,6S,7S,8R)-3,4-dibromo-7-(tert-butyldiphenylsilyloxy)methyl-8-methyl-9-oxabicyclo[4.2.1]nonane 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: 96.0%

(1R,6S,7S,8R)-7-(tert-butyldiphenylsilyloxy)methyl-8-methyl-9-oxabicyclo[4.2.1]non-3-ene (817201-02-8) → (1R,6S,7S,8R)-3,4-dibromo-7-(tert-butyldiphenylsilyloxy)methyl-8-methyl-9-oxabicyclo[4.2.1]nonane (817201-17-5)

Guidance literature:

With bromine; In diethyl ether; at -78 ℃; for 1h;

DOI:10.1021/jo048566j

Reference yield:

exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride (6118-51-0) → (1R,6S,7S,8R)-3,4-dibromo-7-(tert-butyldiphenylsilyloxy)methyl-8-methyl-9-oxabicyclo[4.2.1]nonane (817201-17-5)

Guidance literature:

Multi-step reaction with 15 steps

1: LiAlH₄ / tetrahydrofuran / 20 h / 0 °C

2: 2.92 g / pyridine / 17 h / 20 °C

3: lipase PS (Amano); H₂O / tetrahydrofuran / 480 h / 20 °C

4: imidazole / dimethylformamide / 23 h / 0 °C

5: 1.90 g / NaOMe / methanol / 2 h / 20 °C

6: 96 percent / NaH / tetrahydrofuran / 2 h / 0 °C

7: 85 percent / OsO₄; H₂O; Me₃NO*2H₂O / acetone; 2-methyl-propan-2-ol / 20 h / 0 °C

8: 89 percent / n-Bu₃SnH; AIBN / toluene / 1 h / Heating

9: Pb(OAc)4 / benzene / 0.75 h / 20 °C

10: 2.04 g / NaBH₄ / methanol / 1 h / 20 °C

11: 79 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

12: 96 percent / NaI / butan-2-one / 12 h / Heating

13: 89 percent / benzene; tetrahydrofuran / 20 h / 20 °C

14: 86 percent / [1,3-dimesitylimidazolidin-2-yl]Cl₂(PCy₃)Ru=CHPh / benzene / 6 h / Heating

15: 96 percent / Br₂ / diethyl ether / 1 h / -78 °C

With pyridine; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lead(IV) acetate; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; 2,2'-azobis(isobutyronitrile); trimethylamine-N-oxide; Lipase PS (Amano); water; bromine; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; hexane; N,N-dimethyl-formamide; acetone; toluene; butanone; tert-butyl alcohol; benzene;

DOI:10.1021/jo048566j

Reference yield:

exo-2,3-bis(hydroxymethyl)-7-oxabicyclo[2.2.1]hept-5-ene (106137-27-3,817201-06-2) → (1R,6S,7S,8R)-3,4-dibromo-7-(tert-butyldiphenylsilyloxy)methyl-8-methyl-9-oxabicyclo[4.2.1]nonane (817201-17-5)

Guidance literature:

Multi-step reaction with 14 steps

1: 2.92 g / pyridine / 17 h / 20 °C

2: lipase PS (Amano); H₂O / tetrahydrofuran / 480 h / 20 °C

3: imidazole / dimethylformamide / 23 h / 0 °C

4: 1.90 g / NaOMe / methanol / 2 h / 20 °C

5: 96 percent / NaH / tetrahydrofuran / 2 h / 0 °C

6: 85 percent / OsO₄; H₂O; Me₃NO*2H₂O / acetone; 2-methyl-propan-2-ol / 20 h / 0 °C

7: 89 percent / n-Bu₃SnH; AIBN / toluene / 1 h / Heating

8: Pb(OAc)4 / benzene / 0.75 h / 20 °C

9: 2.04 g / NaBH₄ / methanol / 1 h / 20 °C

10: 79 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

11: 96 percent / NaI / butan-2-one / 12 h / Heating

12: 89 percent / benzene; tetrahydrofuran / 20 h / 20 °C

13: 86 percent / [1,3-dimesitylimidazolidin-2-yl]Cl₂(PCy₃)Ru=CHPh / benzene / 6 h / Heating

14: 96 percent / Br₂ / diethyl ether / 1 h / -78 °C

With pyridine; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lead(IV) acetate; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; 2,2'-azobis(isobutyronitrile); trimethylamine-N-oxide; Lipase PS (Amano); water; bromine; tri-n-butyl-tin hydride; sodium methylate; sodium hydride; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; hexane; N,N-dimethyl-formamide; acetone; toluene; butanone; tert-butyl alcohol; benzene;

DOI:10.1021/jo048566j

upstream raw materials:

(1R,6S,7S,8R)-7-(tert-butyldiphenylsilyloxy)methyl-8-methyl-9-oxabicyclo[4.2.1]non-3-ene

(1R,2R,3S,4S)-2-(1-ethoxyethoxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene

(1S,2S,3R,4R)-2-acetoxymethyl-3-(1-ethoxyethoxy)methyl-7-oxabicyclo[2.2.1]hept-5-ene

(2R,3S,4S,5S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methyl-tetrahydro-furan-2,5-dicarbaldehyde

Downstream raw materials:

(1R,6S,7R,8S)-7-(furan-2-carbonyl)-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-diene

(1R,6S,7S,8R)-7-(tert-butyldiphenylsilyloxy)methyl-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-diene