methyl (2S,4S,6S)-{6-ethyl-2-phenyl[1,3]dioxan-4-yl}acetate

Base Information

• Chemical Name: methyl (2S,4S,6S)-{6-ethyl-2-phenyl[1,3]dioxan-4-yl}acetate
• CAS No.: 1608489-59-3
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• Mol file: 1608489-59-3.mol

Synonyms:methyl (2S,4S,6S)-{6-ethyl-2-phenyl[1,3]dioxan-4-yl}acetate

Chemical Property of methyl (2S,4S,6S)-{6-ethyl-2-phenyl[1,3]dioxan-4-yl}acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S,4S,6S)-{6-ethyl-2-phenyl[1,3]dioxan-4-yl}acetate

There total 7 articles about methyl (2S,4S,6S)-{6-ethyl-2-phenyl[1,3]dioxan-4-yl}acetate 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: 65.0%

methyl (5S)-5-hydroxyhept-2-enoate (1608489-62-8) + benzaldehyde (100-52-7) → methyl (2S,4S,6S)-{6-ethyl-2-phenyl[1,3]dioxan-4-yl}acetate (1608489-59-3)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.1002/ejoc.201301484

Reference yield:

methyl propanoyl acetate (30414-53-0) → methyl (2S,4S,6S)-{6-ethyl-2-phenyl[1,3]dioxan-4-yl}acetate (1608489-59-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: RuBr₂{(S)-2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl}; hydrogen / methanol / 50 °C

2.1: 1H-imidazole / dichloromethane / 20 °C

3.1: diisobutylaluminium hydride / dichloromethane; hexane / 0 °C

4.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 2 h / 20 °C

5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C

5.2: 2 h / 0 °C

6.1: pyridinium p-toluenesulfonate / methanol / 72 h / 50 °C / Inert atmosphere

7.1: potassium tert-butylate / tetrahydrofuran / 0.25 h / 0 °C

With 1H-imidazole; RuBr₂{(S)-2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl}; potassium tert-butylate; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; methanol; hexane; dichloromethane; mineral oil; 5.1: |Horner-Wadsworth-Emmons Olefination / 5.2: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1002/ejoc.201301484

Reference yield:

methyl (S)-3-hydroxyvalerate (42558-50-9) → methyl (2S,4S,6S)-{6-ethyl-2-phenyl[1,3]dioxan-4-yl}acetate (1608489-59-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1H-imidazole / dichloromethane / 20 °C

2.1: diisobutylaluminium hydride / dichloromethane; hexane / 0 °C

3.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 2 h / 20 °C

4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C

4.2: 2 h / 0 °C

5.1: pyridinium p-toluenesulfonate / methanol / 72 h / 50 °C / Inert atmosphere

6.1: potassium tert-butylate / tetrahydrofuran / 0.25 h / 0 °C

With 1H-imidazole; potassium tert-butylate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; methanol; hexane; dichloromethane; mineral oil; 4.1: |Horner-Wadsworth-Emmons Olefination / 4.2: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1002/ejoc.201301484

upstream raw materials:

methyl propanoyl acetate

methyl (S)-3-hydroxyvalerate

methyl (S)-3-(((tert-butyldimethyl)silyl)oxy)pentanoate

(S)-3-(((tert-butyldimethyl)silyl)oxy)pentan-1-ol