(-)-(S)-acetic acid [(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptan-1-yl](2-vinylcyclohex-1-enyl)methyl ester

Base Information

Chemical Name:(-)-(S)-acetic acid [(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptan-1-yl](2-vinylcyclohex-1-enyl)methyl ester
CAS No.:301823-92-7
Molecular Formula:C₃₇H₄₈O₄Si
Molecular Weight:584.871
Hs Code.:

(-)-(S)-acetic acid [(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptan-1-yl](2-vinylcyclohex-1-enyl)methyl ester

Synonyms:(-)-(S)-acetic acid [(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptan-1-yl](2-vinylcyclohex-1-enyl)methyl ester

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Chemical Property of (-)-(S)-acetic acid [(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptan-1-yl](2-vinylcyclohex-1-enyl)methyl ester

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Technology Process of (-)-(S)-acetic acid [(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptan-1-yl](2-vinylcyclohex-1-enyl)methyl ester

There total 21 articles about (-)-(S)-acetic acid [(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptan-1-yl](2-vinylcyclohex-1-enyl)methyl 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: 92.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 471270-09-4
(-)-(S)-acetic acid [(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptan-1-yl](2-formylcyclohex-1-enyl)methyl ester

: 301823-92-7
(-)-(S)-acetic acid [(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptan-1-yl](2-vinylcyclohex-1-enyl)methyl ester

Guidance literature:: Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 1h;

(-)-(S)-acetic acid [(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptan-1-yl](2-formylcyclohex-1-enyl)methyl ester; In tetrahydrofuran; for 0.75h;
DOI:10.1039/b202020n

Reference yield:

: 301823-94-9
(+)-(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptancarboxaldehyde

: 301823-92-7
(-)-(S)-acetic acid [(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptan-1-yl](2-vinylcyclohex-1-enyl)methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 64 percent / CrCl₂ / NiCl₂ / dimethylformamide / 18 h / 50 °C

2.1: 93 percent / LiAlH₄ / diethyl ether / 0.5 h / 20 °C

3.1: 89 percent / imidazole / dimethylformamide / 16 h / 20 °C

4.1: 92 percent / pyridine / 16 h / 20 °C

5.1: 100 percent / CSA / 2 h / 0 °C

6.1: 97 percent / NMO / TPAP / acetone / 2 h

7.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C

7.2: 92 percent / tetrahydrofuran / 0.75 h

With pyridine; 1H-imidazole; chromium dichloride; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; camphor-10-sulfonic acid; tetrapropylammonium perruthennate; nickel dichloride; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide; acetone; 7.2: Wittig olefination;
DOI:10.1039/b202020n

Reference yield:

: 471269-89-3
(+)-(1R,2S,4R,5S)-[5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptan-1-yl]methanol

: 301823-92-7
(-)-(S)-acetic acid [(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptan-1-yl](2-vinylcyclohex-1-enyl)methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 83 percent / SO₃*pyridine; DMSO / CH₂Cl₂ / 3 h / 20 °C

2.1: 64 percent / CrCl₂ / NiCl₂ / dimethylformamide / 18 h / 50 °C

3.1: 93 percent / LiAlH₄ / diethyl ether / 0.5 h / 20 °C

4.1: 89 percent / imidazole / dimethylformamide / 16 h / 20 °C

5.1: 92 percent / pyridine / 16 h / 20 °C

6.1: 100 percent / CSA / 2 h / 0 °C

7.1: 97 percent / NMO / TPAP / acetone / 2 h

8.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C

8.2: 92 percent / tetrahydrofuran / 0.75 h

With pyridine; 1H-imidazole; chromium dichloride; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; pyridine-SO₃ complex; camphor-10-sulfonic acid; dimethyl sulfoxide; tetrapropylammonium perruthennate; nickel dichloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; 8.2: Wittig olefination;
DOI:10.1039/b202020n