(4R,6S,7S)-7-(benzyloxy)-4,6-dimethylnonan-3-one

Base Information

• Chemical Name: (4R,6S,7S)-7-(benzyloxy)-4,6-dimethylnonan-3-one
• CAS No.: 1360170-65-5
• Molecular Formula: C₁₈H₂₈O₂
• Molecular Weight: 276.419
• Mol file: 1360170-65-5.mol

Synonyms:(4R,6S,7S)-7-(benzyloxy)-4,6-dimethylnonan-3-one

Chemical Property of (4R,6S,7S)-7-(benzyloxy)-4,6-dimethylnonan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,6S,7S)-7-(benzyloxy)-4,6-dimethylnonan-3-one

There total 18 articles about (4R,6S,7S)-7-(benzyloxy)-4,6-dimethylnonan-3-one 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: 92.0%

C18H30O2 (1360170-70-2) → (4R,6S,7S)-7-(benzyloxy)-4,6-dimethylnonan-3-one (1360170-65-5)

Guidance literature:

With dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; at 0 - 20 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.11.013

Reference yield:

(2S,3S,4R)-3-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxan-4-yl)-2-methylpentan-1-ol → (4R,6S,7S)-7-(benzyloxy)-4,6-dimethylnonan-3-one (1360170-65-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

2.1: ammonia; lithium / tetrahydrofuran / 0.17 h / -33 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

3.2: 0.5 h / 0 °C / Inert atmosphere

3.3: 0 - 20 °C / Inert atmosphere

4.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 2 h / Inert atmosphere; Reflux

5.1: methanol; pyridinium p-toluenesulfonate / 3 h / 0 - 20 °C / Inert atmosphere

6.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

7.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere; Reflux

7.2: 0 °C

8.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere; Reflux

8.2: 4 h / Inert atmosphere; Reflux

9.1: methanol; toluene-4-sulfonic acid / 6 h / 0 - 20 °C / Inert atmosphere

10.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

11.1: magnesium / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

11.2: 0 - 20 °C / Inert atmosphere

11.3: 20 °C

12.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

With methanol; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); ammonia; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; lithium; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; magnesium; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; toluene; mineral oil; 4.1: Barton-McCombie deoxygenation / 11.2: Grignard reaction;

DOI:10.1016/j.tetasy.2011.11.013

Reference yield:

(4S,5S)-4-ethyl-5-methyl-2-phenyl-1,3-dioxane (1360170-47-3) → (4R,6S,7S)-7-(benzyloxy)-4,6-dimethylnonan-3-one (1360170-65-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -15 °C / Inert atmosphere

1.2: 2 h / 20 °C

2.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

3.1: titanium tetrachloride / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

3.2: 0.5 h / -78 °C / Inert atmosphere

4.1: methanol; sodium tetrahydroborate / 1 h / 0 °C / Inert atmosphere

5.1: 1H-imidazole / dichloromethane / 2 h / 0 °C / Inert atmosphere

6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

6.2: 0.5 h / 0 °C / Inert atmosphere

6.3: 0 - 20 °C / Inert atmosphere

7.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 2 h / Inert atmosphere; Reflux

8.1: methanol; toluene-4-sulfonic acid / 0.5 h / 0 - 20 °C / Inert atmosphere

9.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

10.1: magnesium / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

10.2: 0 - 20 °C / Inert atmosphere

10.3: 20 °C

11.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; methanol; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; magnesium; dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; toluene; mineral oil; 7.1: Barton-McCombie deoxygenation / 10.2: Grignard reaction;

DOI:10.1016/j.tetasy.2011.11.013

upstream raw materials:

(4S,5S)-4-ethyl-5-methyl-2-phenyl-1,3-dioxane

(2S,3S)-3-(benzyloxy)-2-methylpentan-1-ol

[S-(R*,R*)]-2-methyl-3-(phenylmethoxy)pentanal

(2R,3S,4S,5S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-5-(benzyloxy)-3-hydroxy-2,4-dimethylheptan-1-one

Downstream raw materials:

(4R,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone

(4R,6S,7S)-7-acetoxy-4,6-dimethyl-3-nonanone

Refernces