(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-1-[(2R*)-tetrahydropyran-2-yloxymethyl]-7-oxabicyclo[2.2.1]heptane-2-carbaldehyde

Base Information

Chemical Name:(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-1-[(2R*)-tetrahydropyran-2-yloxymethyl]-7-oxabicyclo[2.2.1]heptane-2-carbaldehyde
CAS No.:471269-88-2
Molecular Formula:C₃₁H₄₂O₅Si
Molecular Weight:522.757
Hs Code.:

Synonyms:(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-1-[(2R*)-tetrahydropyran-2-yloxymethyl]-7-oxabicyclo[2.2.1]heptane-2-carbaldehyde

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Chemical Property of (1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-1-[(2R*)-tetrahydropyran-2-yloxymethyl]-7-oxabicyclo[2.2.1]heptane-2-carbaldehyde

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Technology Process of (1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-1-[(2R*)-tetrahydropyran-2-yloxymethyl]-7-oxabicyclo[2.2.1]heptane-2-carbaldehyde

There total 17 articles about (1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-1-[(2R*)-tetrahydropyran-2-yloxymethyl]-7-oxabicyclo[2.2.1]heptane-2-carbaldehyde 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: 88.0%

: 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

: 471269-88-2
(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-1-[(2R*)-tetrahydropyran-2-yloxymethyl]-7-oxabicyclo[2.2.1]heptane-2-carbaldehyde

Guidance literature:: With N-methyl-2-indolinone; tetrapropylammonium perruthennate; In acetone; for 2h;
DOI:10.1039/b202020n

Reference yield:

: 470690-19-8
(1R,2S,4S)-1-hydroxymethyl-3,3-dimethyl-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid ethyl ester

: 471269-88-2
(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-1-[(2R*)-tetrahydropyran-2-yloxymethyl]-7-oxabicyclo[2.2.1]heptane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: 91 percent / p-TsOH*H₂O / 16 h / 20 °C

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

2.2: 76 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 3 h

3.1: 89 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

4.1: 95 percent / LiAlH₄ / diethyl ether / 0.25 h / 20 °C

5.1: 88 percent / NMO / TPAP / acetone / 2 h

With 1H-imidazole; lithium aluminium tetrahydride; N-methyl-2-indolinone; bis-(1,2-dimethylpropyl)borane; toluene-4-sulfonic acid; tetrapropylammonium perruthennate; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;
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

: 471269-88-2
(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-1-[(2R*)-tetrahydropyran-2-yloxymethyl]-7-oxabicyclo[2.2.1]heptane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 4 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

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