(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

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-carboxylic acid ethyl ester
CAS No.:301823-97-2
Molecular Formula:C₃₃H₄₆O₆Si
Molecular Weight:566.81
Hs Code.:

(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

Synonyms:(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

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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-carboxylic acid ethyl ester

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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-carboxylic acid ethyl ester

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-carboxylic acid ethyl 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: 89.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 471269-86-0
(1R,2S,4R,5S)-5-hydroxy-3,3-dimethyl-1-[(2R*)-tetrahydropyran-2-yloxymethyl]-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester

: 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

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 16h;
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

: 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

Guidance literature:: Multi-step reaction with 3 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

With 1H-imidazole; bis-(1,2-dimethylpropyl)borane; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1039/b202020n

Reference yield:

: 110-87-2
3,4-dihydro-2H-pyran

: 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

Guidance literature:: Multi-step reaction with 3 steps

1.1: p-TsOH / CH₂Cl₂

2.1: disiamylborane / tetrahydrofuran

2.2: aq. H₂O₂; NaOH

3.1: imidazole / CH₂Cl₂

With 1H-imidazole; bis-(1,2-dimethylpropyl)borane; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; 1.1: Addition / 2.1: Hydroboration / 2.2: Oxidation / 3.1: Etherification;
DOI:10.1039/b003757p