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

Base Information

Chemical Name:(+)-(1R,2S,4R,5S)-[5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-2-vinyl-7-oxabicyclo[2.2.1]heptan-1-yl]methanol
CAS No.:471269-89-3
Molecular Formula:C₂₇H₃₆O₃Si
Molecular Weight:436.667
Hs Code.:

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

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

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

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

: 471269-82-6
(1R,2S,4R,5S)-tert-butyl{6,6-dimethyl-4-[(2R*)-tetrahydropyran-2-yloxymethyl]-5-vinyl-7-oxabicyclo[2.2.1]heptan-2-yloxy}diphenylsilane

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

Guidance literature:: With acetic acid; In tetrahydrofuran; at 60 ℃; for 16h;
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

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

Guidance literature:: Multi-step reaction with 3 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

With n-butyllithium; N-methyl-2-indolinone; acetic acid; tetrapropylammonium perruthennate; In tetrahydrofuran; hexane; 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

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

Guidance literature:: Multi-step reaction with 6 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

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