(+)-(2S,3S,4S,6R)-6-(2-benzyloxyethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyl-2-(2-oxoethyl)-tetrahydropyran

Base Information

Chemical Name:(+)-(2S,3S,4S,6R)-6-(2-benzyloxyethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyl-2-(2-oxoethyl)-tetrahydropyran
CAS No.:858676-39-8
Molecular Formula:C₂₃H₃₈O₄Si
Molecular Weight:406.638
Hs Code.:

Synonyms:(+)-(2S,3S,4S,6R)-6-(2-benzyloxyethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyl-2-(2-oxoethyl)-tetrahydropyran

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Chemical Property of (+)-(2S,3S,4S,6R)-6-(2-benzyloxyethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyl-2-(2-oxoethyl)-tetrahydropyran

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Technology Process of (+)-(2S,3S,4S,6R)-6-(2-benzyloxyethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyl-2-(2-oxoethyl)-tetrahydropyran

There total 6 articles about (+)-(2S,3S,4S,6R)-6-(2-benzyloxyethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyl-2-(2-oxoethyl)-tetrahydropyran 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:

: 858676-38-7
(+)-(2S,3S,4S,6R)-6-(2-benzyloxyethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyl-2-(2-hydroxyethyl)-tetrahydropyran

: 858676-39-8
(+)-(2S,3S,4S,6R)-6-(2-benzyloxyethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyl-2-(2-oxoethyl)-tetrahydropyran

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/ol050840o

Reference yield:

: 853193-61-0
(-)-(3S,5E)-1-benzyloxyhept-5-en-3-ol

: 858676-39-8
(+)-(2S,3S,4S,6R)-6-(2-benzyloxyethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyl-2-(2-oxoethyl)-tetrahydropyran

Guidance literature:: Multi-step reaction with 5 steps

1.1: CH₂Cl₂ / 3.5 h / 20 °C

2.1: potassium carbonate; methanol / 1 h

3.1: imidazole; DMAP / dimethylformamide / 7 h / 20 °C

4.1: 9-BBN / tetrahydrofuran / 7 h / 20 °C

4.2: hydrogen peroxide; NaOH / tetrahydrofuran; H₂O / 1 h / 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; methanol; dmap; 9-borabicyclo[3.3.1]nonane dimer; potassium carbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Prins cyclization;
DOI:10.1021/ol050840o

Reference yield:

: 858676-36-5
(+)-(2S,3R,4S,6R)-6-(2-benzyloxyethyl)-4-hydroxy-3-methyl-2-ethenyltetrahydropyran

: 858676-39-8
(+)-(2S,3S,4S,6R)-6-(2-benzyloxyethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyl-2-(2-oxoethyl)-tetrahydropyran

Guidance literature:: Multi-step reaction with 3 steps

1.1: imidazole; DMAP / dimethylformamide / 7 h / 20 °C

2.1: 9-BBN / tetrahydrofuran / 7 h / 20 °C

2.2: hydrogen peroxide; NaOH / tetrahydrofuran; H₂O / 1 h / 20 °C

3.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With 1H-imidazole; dmap; 9-borabicyclo[3.3.1]nonane dimer; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol050840o