(2S,3S,4S,6R)-[6-(2-benzyloxy-ethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyltetrahydropyran-2-yl]-acetic acid

Base Information

• Chemical Name: (2S,3S,4S,6R)-[6-(2-benzyloxy-ethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyltetrahydropyran-2-yl]-acetic acid
• CAS No.: 858676-40-1
• Molecular Formula: C₂₃H₃₈O₅Si
• Molecular Weight: 422.637
• Mol file: 858676-40-1.mol

Synonyms:(2S,3S,4S,6R)-[6-(2-benzyloxy-ethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyltetrahydropyran-2-yl]-acetic acid

Chemical Property of (2S,3S,4S,6R)-[6-(2-benzyloxy-ethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyltetrahydropyran-2-yl]-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,6R)-[6-(2-benzyloxy-ethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyltetrahydropyran-2-yl]-acetic acid

There total 7 articles about (2S,3S,4S,6R)-[6-(2-benzyloxy-ethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyltetrahydropyran-2-yl]-acetic acid 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:

(+)-(2S,3S,4S,6R)-6-(2-benzyloxyethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyl-2-(2-oxoethyl)-tetrahydropyran (858676-39-8) + methanol (67-56-1) → (+)-methyl (2S,3S,4S,6R)-[6-(2-benzyloxy-ethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyl-tetrahydropyran-2-yl]-acetate (858676-41-2) + (2S,3S,4S,6R)-[6-(2-benzyloxy-ethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyltetrahydropyran-2-yl]-acetic acid (858676-40-1)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; at 20 ℃; for 26h;

DOI:10.1021/ol050840o

Reference yield:

(-)-(3S,5E)-1-benzyloxyhept-5-en-3-ol (853193-61-0) → (2S,3S,4S,6R)-[6-(2-benzyloxy-ethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyltetrahydropyran-2-yl]-acetic acid (858676-40-1)

Guidance literature:

Multi-step reaction with 6 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

6.1: pyridinium dichromate / dimethylformamide / 26 h / 20 °C

With 1H-imidazole; methanol; dmap; dipyridinium dichromate; 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:

(+)-(2S,3R,4S,6R)-6-(2-benzyloxyethyl)-4-hydroxy-3-methyl-2-ethenyltetrahydropyran (858676-36-5) → (2S,3S,4S,6R)-[6-(2-benzyloxy-ethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyltetrahydropyran-2-yl]-acetic acid (858676-40-1)

Guidance literature:

Multi-step reaction with 4 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

4.1: pyridinium dichromate / dimethylformamide / 26 h / 20 °C

With 1H-imidazole; dmap; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol050840o

upstream raw materials:

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

methanol

(-)-(3S,5E)-1-benzyloxyhept-5-en-3-ol

(+)-(2S,3R,4S,6R)-6-(2-benzyloxyethyl)-4-hydroxy-3-methyl-2-ethenyltetrahydropyran

Downstream raw materials:

(+)-methyl (2S,3S,4S,6R)-[6-(2-benzyloxy-ethyl)-4-(tert-butyldimethylsilanyloxy)-3-methyl-tetrahydropyran-2-yl]-acetate