ethyl 2-((2S,4S,6S)-6-(((2S,4S,6S)-6-(2-hydroxyethyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)acetate

Base Information

• Chemical Name: ethyl 2-((2S,4S,6S)-6-(((2S,4S,6S)-6-(2-hydroxyethyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)acetate
• CAS No.: 1443040-60-5
• Molecular Formula: C₂₇H₃₄O₇
• Molecular Weight: 470.563
• Mol file: 1443040-60-5.mol

Synonyms:ethyl 2-((2S,4S,6S)-6-(((2S,4S,6S)-6-(2-hydroxyethyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)acetate

Chemical Property of ethyl 2-((2S,4S,6S)-6-(((2S,4S,6S)-6-(2-hydroxyethyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-((2S,4S,6S)-6-(((2S,4S,6S)-6-(2-hydroxyethyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)acetate

There total 17 articles about ethyl 2-((2S,4S,6S)-6-(((2S,4S,6S)-6-(2-hydroxyethyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-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: 92.0%

ethyl 2-((2S,4S,6S)-6-(((2S,4S,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)acetate (1443040-59-2) → ethyl 2-((2S,4S,6S)-6-(((2S,4S,6S)-6-(2-hydroxyethyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)acetate (1443040-60-5)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ja404401f

Reference yield:

methyl 2-((2S,4S,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetate (1443040-52-5) → ethyl 2-((2S,4S,6S)-6-(((2S,4S,6S)-6-(2-hydroxyethyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)acetate (1443040-60-5)

Guidance literature:

Multi-step reaction with 5 steps

1: diisobutylaluminium hydride / hexane / -78 °C / Inert atmosphere

2: (3aS,7aS)-1,3-bis[(4-bromophenyl)methyl]-2-chlorooctahydro-2-(2-propenyl)-1H-1,3,2-benzodiazasilole; scandium tris(trifluoromethanesulfonate) / dichloromethane / 12 h / -10 °C / Inert atmosphere

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 3 h / 20 °C / Inert atmosphere

4: potassium tert-butylate / tetrahydrofuran / 0 °C / Inert atmosphere

5: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2 h / 0 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; potassium tert-butylate; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; scandium tris(trifluoromethanesulfonate); (3aS,7aS)-1,3-bis[(4-bromophenyl)methyl]-2-chlorooctahydro-2-(2-propenyl)-1H-1,3,2-benzodiazasilole; In tetrahydrofuran; hexane; dichloromethane; water;

DOI:10.1021/ja404401f

Reference yield:

(R)-1-((2S,4R,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-ol (1443040-54-7) → ethyl 2-((2S,4S,6S)-6-(((2S,4S,6S)-6-(2-hydroxyethyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)acetate (1443040-60-5)

Guidance literature:

Multi-step reaction with 3 steps

1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 3 h / 20 °C / Inert atmosphere

2: potassium tert-butylate / tetrahydrofuran / 0 °C / Inert atmosphere

3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2 h / 0 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; potassium tert-butylate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ja404401f

upstream raw materials:

ethyl 2-((2S,4S,6S)-6-(((2S,4S,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)acetate

1-[(hex-5-yn-1-yloxy)methyl]-4-methoxybenzene

methyl 7-((4-methoxybenzyl)oxy)hept-2-ynoate

(2E,4E)-methyl 7-((4-methoxybenzyl)oxy)hepta-2,4-dienoate

Downstream raw materials:

ethyl 2-((2S,4S,6S)-6-(((2R,4R,6R)-6-(2-oxoheptadec-3-yn-1-yl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)acetate

ethyl 2-((2S,4S,6S)-6-(((2S,4S,6S)-6-((S)-2-hydroxyheptadec-3-yn-1-yl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)acetate

(R)-1-((2R,4R,6S)-6-(((2R,4R,6R)-6-((R)-2-hydroxypent-4-en-1-yl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)heptadecan-2-yl acetate