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

Base Information

Chemical Name:(+)-(2S,3S,4S,6R)-6-(2-benzyloxyethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyl-2-(2-hydroxyethyl)-tetrahydropyran
CAS No.:858676-38-7
Molecular Formula:C₂₃H₄₀O₄Si
Molecular Weight:408.654
Hs Code.:

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

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

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

There total 5 articles about (+)-(2S,3S,4S,6R)-6-(2-benzyloxyethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyl-2-(2-hydroxyethyl)-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:

: 858676-37-6
(+)-(2S,3R,4S,6R)-6-(2-benzyloxyethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyl-2-ethenyl-tetrahydropyran

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

Guidance literature:: (+)-(2S,3R,4S,6R)-6-(2-benzyloxyethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyl-2-ethenyl-tetrahydropyran; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 20 ℃; for 7h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 20 ℃; for 1h;
DOI:10.1021/ol050840o

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; methanol; dmap; 9-borabicyclo[3.3.1]nonane dimer; potassium carbonate; 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

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

Guidance literature:: Multi-step reaction with 2 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

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