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

Base Information

Chemical Name:(+)-(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptancarboxaldehyde
CAS No.:301823-94-9
Molecular Formula:C₂₇H₃₄O₃Si
Molecular Weight:434.651
Hs Code.:

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

Suppliers and Price of (+)-(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptancarboxaldehyde

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (+)-(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptancarboxaldehyde

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

Safty Information:

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Hazard Codes:

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Technology Process of (+)-(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptancarboxaldehyde

There total 16 articles about (+)-(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptancarboxaldehyde 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: 83.0%

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

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

Guidance literature:: With pyridine-SO₃ complex; dimethyl sulfoxide; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1039/b202020n

Reference yield:

: 471269-87-1
(1R,2S,4R,5S)-5-{(tert-butyldiphenylsilyloxy)-3,3-dimethyl-1-[(2R*)-tetrahydropyran-2-yloxymethyl]-7-oxabicyclo[2.2.1]heptane-2-yl}methanol

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

Guidance literature:: Multi-step reaction with 4 steps

1.1: 88 percent / NMO / TPAP / acetone / 2 h

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

2.2: 89 percent / tetrahydrofuran / 2 h / 20 °C

3.1: 96 percent / aq. HOAc / tetrahydrofuran / 16 h / 60 °C

4.1: 83 percent / SO₃*pyridine; DMSO / CH₂Cl₂ / 3 h / 20 °C

With n-butyllithium; N-methyl-2-indolinone; pyridine-SO₃ complex; acetic acid; dimethyl sulfoxide; tetrapropylammonium perruthennate; In tetrahydrofuran; hexane; dichloromethane; acetone; 2.2: Wittig olefination;
DOI:10.1039/b202020n

Reference yield:

: 301823-96-1
(1R,2S,4S)-3,3-dimethyl-1-[(2R*)-tetrahydropyran-2-yloxymethyl]-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester

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

Guidance literature:: Multi-step reaction with 7 steps

1.1: disiamylborane / tetrahydrofuran / 16 h / -20 °C

1.2: 76 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 3 h

2.1: 89 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

3.1: 95 percent / LiAlH₄ / diethyl ether / 0.25 h / 20 °C

4.1: 88 percent / NMO / TPAP / acetone / 2 h

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

5.2: 89 percent / tetrahydrofuran / 2 h / 20 °C

6.1: 96 percent / aq. HOAc / tetrahydrofuran / 16 h / 60 °C

7.1: 83 percent / SO₃*pyridine; DMSO / CH₂Cl₂ / 3 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; pyridine-SO₃ complex; bis-(1,2-dimethylpropyl)borane; acetic acid; dimethyl sulfoxide; tetrapropylammonium perruthennate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetone; 5.2: Wittig olefination;
DOI:10.1039/b202020n