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

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-yl}methanol
CAS No.:471269-87-1
Molecular Formula:C₃₁H₄₄O₅Si
Molecular Weight:524.773
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-yl}methanol

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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-1-[(2R*)-tetrahydropyran-2-yloxymethyl]-7-oxabicyclo[2.2.1]heptane-2-yl}methanol

Chemical Property:

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

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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-yl}methanol

There total 15 articles about (1R,2S,4R,5S)-5-{(tert-butyldiphenylsilyloxy)-3,3-dimethyl-1-[(2R*)-tetrahydropyran-2-yloxymethyl]-7-oxabicyclo[2.2.1]heptane-2-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: 95.0%

: 301823-97-2
(1R,2S,4R,5S)-5-(tert-butyldiphenylsilyloxy)-3,3-dimethyl-1-[(2R*)-tetrahydropyran-2-yloxymethyl]-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

: 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

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at 20 ℃; for 0.25h;
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

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

Guidance literature:: Multi-step reaction with 4 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

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

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

Guidance literature:: Multi-step reaction with 3 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

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