(+)-(4S,6R)-4-[2-(benzyloxy)ethyl]-2,2,6-trimethyl-1,3-dioxane

Base Information

• Chemical Name: (+)-(4S,6R)-4-[2-(benzyloxy)ethyl]-2,2,6-trimethyl-1,3-dioxane
• CAS No.: 944394-26-7
• Molecular Formula: C₁₆H₂₄O₃
• Molecular Weight: 264.365
• Mol file: 944394-26-7.mol

Synonyms:(+)-(4S,6R)-4-[2-(benzyloxy)ethyl]-2,2,6-trimethyl-1,3-dioxane

Chemical Property of (+)-(4S,6R)-4-[2-(benzyloxy)ethyl]-2,2,6-trimethyl-1,3-dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(4S,6R)-4-[2-(benzyloxy)ethyl]-2,2,6-trimethyl-1,3-dioxane

There total 11 articles about (+)-(4S,6R)-4-[2-(benzyloxy)ethyl]-2,2,6-trimethyl-1,3-dioxane 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:

4-benzyloxybutanal (5470-84-8) → (+)-(4S,6R)-4-[2-(benzyloxy)ethyl]-2,2,6-trimethyl-1,3-dioxane (944394-26-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C

1.2: NaBH₄ / acetonitrile; methanol / 0.17 h

1.3: CuSO₄*5H₂O / methanol / 10 h / 0 °C

2.1: triethylamine / CH₂Cl₂ / 0.25 h / 0 °C

3.1: K₂CO₃ / methanol / 1 h / 25 °C

4.1: Mg / tetrahydrofuran / 0 °C

4.2: CuI / tetrahydrofuran / 0.5 h / -40 °C

4.3: tetrahydrofuran / 1 h / -40 °C

5.1: 4-(dimethylamino)pyridine / acetonitrile / 5 h / 25 °C

5.2: imidazole / ethanol / 0.25 h / 25 °C

6.1: N-iodosuccinimide / acetonitrile / -40 - 0 °C

7.1: K₂CO₃; MeOH / 0 - 25 °C

8.1: LiAlH₄ / tetrahydrofuran / 6 h / 50 °C

9.1: camphorsulfonic acid / 4 h / 25 °C

With methanol; dmap; N-iodo-succinimide; lithium aluminium tetrahydride; camphor-10-sulfonic acid; potassium carbonate; magnesium; triethylamine; Nitrosobenzene; D-Prolin; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1016/j.tetasy.2007.04.008

Reference yield:

4-benzyloxy-butan-1-ol (4541-14-4) → (+)-(4S,6R)-4-[2-(benzyloxy)ethyl]-2,2,6-trimethyl-1,3-dioxane (944394-26-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 95.3 percent / IBX / dimethylsulfoxide / 2 h / 25 °C

2.1: nitrosobenzene; D-proline / acetonitrile / 24 h / -20 °C

2.2: NaBH₄ / acetonitrile; methanol / 0.17 h

2.3: CuSO₄*5H₂O / methanol / 10 h / 0 °C

3.1: triethylamine / CH₂Cl₂ / 0.25 h / 0 °C

4.1: K₂CO₃ / methanol / 1 h / 25 °C

5.1: Mg / tetrahydrofuran / 0 °C

5.2: CuI / tetrahydrofuran / 0.5 h / -40 °C

5.3: tetrahydrofuran / 1 h / -40 °C

6.1: 4-(dimethylamino)pyridine / acetonitrile / 5 h / 25 °C

6.2: imidazole / ethanol / 0.25 h / 25 °C

7.1: N-iodosuccinimide / acetonitrile / -40 - 0 °C

8.1: K₂CO₃; MeOH / 0 - 25 °C

9.1: LiAlH₄ / tetrahydrofuran / 6 h / 50 °C

10.1: camphorsulfonic acid / 4 h / 25 °C

With methanol; dmap; N-iodo-succinimide; lithium aluminium tetrahydride; camphor-10-sulfonic acid; potassium carbonate; magnesium; triethylamine; Nitrosobenzene; D-Prolin; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; acetonitrile;

DOI:10.1016/j.tetasy.2007.04.008

Reference yield:

tert-butyl (R)-1-(benzyloxy)hex-5-en-3-yl carbonate (204448-48-6) → (+)-(4S,6R)-4-[2-(benzyloxy)ethyl]-2,2,6-trimethyl-1,3-dioxane (944394-26-7)

Guidance literature:

Multi-step reaction with 4 steps

1: N-iodosuccinimide / acetonitrile / -40 - 0 °C

2: K₂CO₃; MeOH / 0 - 25 °C

3: LiAlH₄ / tetrahydrofuran / 6 h / 50 °C

4: camphorsulfonic acid / 4 h / 25 °C

With methanol; N-iodo-succinimide; lithium aluminium tetrahydride; camphor-10-sulfonic acid; potassium carbonate; In tetrahydrofuran; acetonitrile;

DOI:10.1016/j.tetasy.2007.04.008

upstream raw materials:

(+)-(2R,4S)-6-(benzyloxy)hexane-2,4-diol

2,2-dimethoxy-propane

tert-butyl (R)-1-(benzyloxy)hex-5-en-3-yl carbonate

4-benzyloxy-butan-1-ol

Downstream raw materials:

(R)-1-methyl-2-[(S)-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl 3-(3,4-dihydroxyphenyl)propanoate

(-)-<5(S),7(R)>-7-<5-(oct-2-enolide)-3',4'-bis-(t-butyldimethylsilyloxy)>-dihydrocinnamate