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

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]-N-methoxy-N-methylacetamide
• CAS No.: 1222190-51-3
• Molecular Formula: C₃₂H₄₅NO₆
• Molecular Weight: 539.712
• Mol file: 1222190-51-3.mol

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]-N-methoxy-N-methylacetamide

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]-N-methoxy-N-methylacetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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]-N-methoxy-N-methylacetamide

There total 11 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]-N-methoxy-N-methylacetamide 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: 86.0%

(S,E)-6-[(2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]-5-hydroxy-N-methoxy-N-methylhex-2-enamide (1222190-50-2) + benzaldehyde (100-52-7) → 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)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 4h; diastereoselective reaction;

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]-N-methoxy-N-methylacetamide (1222190-51-3)

Guidance literature:

Multi-step reaction with 8 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

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; 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]-N-methoxy-N-methylacetamide (1222190-51-3)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1002/ejoc.201100888

upstream raw materials:

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

benzaldehyde

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

Downstream 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]acetaldehyde

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

(S)-1-[(2S,4S,6S)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-ol

C₃₆H₄₈O₆