2-[(2R,4R,6R)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]acetaldehyde

Base Information

• Chemical Name: 2-[(2R,4R,6R)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]acetaldehyde
• CAS No.: 1222190-41-1
• Molecular Formula: C₃₀H₄₀O₅
• Molecular Weight: 480.645

Synonyms:2-[(2R,4R,6R)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]acetaldehyde

Chemical Property of 2-[(2R,4R,6R)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]acetaldehyde

Chemical Property:

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Technology Process of 2-[(2R,4R,6R)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]acetaldehyde

There total 12 articles about 2-[(2R,4R,6R)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]acetaldehyde 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: 83.0%

2-[(2R,4R,6R)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]-N-methoxy-N-methylacetamide (1222190-51-3) → 2-[(2R,4R,6R)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]acetaldehyde (1222190-41-1)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2010.02.070

Reference yield:

Octanal (124-13-0) → 2-[(2R,4R,6R)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]acetaldehyde (1222190-41-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol / toluene / 36 h / -15 °C / Molecular sieve

2.1: ozone / dichloromethane / 0.08 h / -78 °C

2.2: 18 h / 20 °C

3.1: potassium tert-butylate / tetrahydrofuran / 4 h / 0 °C

4.1: magnesium / tetrahydrofuran; ethylene dibromide / 2 h / 20 °C

5.1: lithium aluminium tetrahydride; lithium iodide / 0.5 h / -100 - -40 °C

6.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 4 h / 20 °C

7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.5 h / 20 °C

7.2: 24 h / 20 °C

8.1: potassium tert-butylate / tetrahydrofuran / 6 h / 4 °C

9.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

With 2,6-dimethylpyridine; titanium(IV) isopropylate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; potassium tert-butylate; (S)-[1,1']-binaphthalenyl-2,2'-diol; diisobutylaluminium hydride; ozone; magnesium; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; lithium iodide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethylene dibromide; toluene; acetonitrile; 1.1: Keck allylation / 2.2: Wittig-Horner reaction / 7.1: Wittig-Horner reaction / 7.2: Wittig-Horner reaction / 8.1: Michael condensation;

DOI:10.1002/ejoc.201100888

Reference yield:

1-[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-one (1222190-49-9) → 2-[(2R,4R,6R)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]acetaldehyde (1222190-41-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium aluminium tetrahydride; lithium iodide / 0.5 h / -100 - -40 °C

2.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 4 h / 20 °C

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.5 h / 20 °C

3.2: 24 h / 20 °C

4.1: potassium tert-butylate / tetrahydrofuran / 6 h / 4 °C

5.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 0.5 h / -78 °C / Inert atmosphere

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; potassium tert-butylate; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; lithium iodide; In tetrahydrofuran; 1,4-dioxane; water; toluene; acetonitrile; 3.1: Wittig-Horner reaction / 3.2: Wittig-Horner reaction / 4.1: Michael condensation;

DOI:10.1002/ejoc.201100888

upstream raw materials:

2-[(2R,4R,6R)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]-N-methoxy-N-methylacetamide

1-[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-one

(S)-1-((2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-ol

(S,E)-6-[(2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]-5-hydroxy-N-methoxy-N-methylhex-2-enamide

Downstream raw materials:

(Z)-methyl 4-((2S,4S,6S)-6-(((2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)but-2-enoate

ethyl (Z)-4-[(2S,4S,6S)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]but-2-enoate

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