(2E,2'R,4'S,5'R) methyl 3-[5'-acetyloxy-2'-phenyl-1',3'-dioxan-4'-yl]-2-propenoate

Base Information

• Chemical Name: (2E,2'R,4'S,5'R) methyl 3-[5'-acetyloxy-2'-phenyl-1',3'-dioxan-4'-yl]-2-propenoate
• CAS No.: 653565-49-2
• Molecular Formula: C₁₆H₁₈O₆
• Molecular Weight: 306.315

Synonyms:(2E,2'R,4'S,5'R) methyl 3-[5'-acetyloxy-2'-phenyl-1',3'-dioxan-4'-yl]-2-propenoate

Chemical Property of (2E,2'R,4'S,5'R) methyl 3-[5'-acetyloxy-2'-phenyl-1',3'-dioxan-4'-yl]-2-propenoate

Chemical Property:

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Technology Process of (2E,2'R,4'S,5'R) methyl 3-[5'-acetyloxy-2'-phenyl-1',3'-dioxan-4'-yl]-2-propenoate

There total 2 articles about (2E,2'R,4'S,5'R) methyl 3-[5'-acetyloxy-2'-phenyl-1',3'-dioxan-4'-yl]-2-propenoate 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: 100.0%

acetic anhydride (108-24-7) + methyl 3-((2′R,4′S,5′R)-5′-hydroxy-2′-phenyl-1′,3′-dioxan-4′-yl)acrylate (653565-47-0) → (2E,2'R,4'S,5'R) methyl 3-[5'-acetyloxy-2'-phenyl-1',3'-dioxan-4'-yl]-2-propenoate (653565-49-2)

Guidance literature:

With pyridine; at 20 ℃; for 2h;

DOI:10.1021/jo035223x

Reference yield:

[2R,4R,5R]-5-hydroxy-2-phenyl-[1,3]dioxane-4-carbaldehyde (81577-69-7) → (2E,2'R,4'S,5'R) methyl 3-[5'-acetyloxy-2'-phenyl-1',3'-dioxan-4'-yl]-2-propenoate (653565-49-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LiHMDS / tetrahydrofuran / 0.25 h / 0 °C

1.2: 80.7 percent / tetrahydrofuran / 0.37 h / 0 °C

2.1: 100 percent / pyridine / 2 h / 20 °C

With pyridine; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1021/jo035223x

Reference yield: 61.0%

(2E,2'R,4'S,5'R) methyl 3-[5'-acetyloxy-2'-phenyl-1',3'-dioxan-4'-yl]-2-propenoate (653565-49-2) → (2R,3R,4E)-2-(acetyloxy)-3-bromo-6-methoxy-6-oxo-4-hexenyl benzoate

Guidance literature:

With N-Bromosuccinimide; dibenzoyl peroxide; In chlorobenzene; at 70 ℃; for 3h;

DOI:10.1021/jo035223x

upstream raw materials:

acetic anhydride

methyl 3-((2′R,4′S,5′R)-5′-hydroxy-2′-phenyl-1′,3′-dioxan-4′-yl)acrylate

[2R,4R,5R]-5-hydroxy-2-phenyl-[1,3]dioxane-4-carbaldehyde

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