Acetic acid (3aS,4R,5S,6aR)-4-acetoxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

Base Information

• Chemical Name: Acetic acid (3aS,4R,5S,6aR)-4-acetoxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester
• CAS No.: 107796-38-3
• Molecular Formula: C₁₂H₁₆O₆
• Molecular Weight: 256.255

Synonyms:Acetic acid (3aS,4R,5S,6aR)-4-acetoxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

Chemical Property of Acetic acid (3aS,4R,5S,6aR)-4-acetoxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

Chemical Property:

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SDS file from LookChem

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Technology Process of Acetic acid (3aS,4R,5S,6aR)-4-acetoxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester

There total 1 articles about Acetic acid (3aS,4R,5S,6aR)-4-acetoxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 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: 63.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one (34638-25-0,38110-77-9,43119-28-4,54483-22-6,26054-46-6) + acetic anhydride (108-24-7) → Acetic acid (3aS,4R,5S,6aR)-4-acetoxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (107796-38-3)

Guidance literature:

formaldehyd; (1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one; With sulfuric acid; In acetic acid;

acetic anhydride; With pyridine; dmap; In dichloromethane;

DOI:10.1016/S0968-0896(02)00090-1

Reference yield: 92.0%

Acetic acid (3aS,4R,5S,6aR)-4-acetoxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (107796-38-3) → <3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one (76704-05-7)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1016/S0968-0896(02)00090-1

Reference yield:

Acetic acid (3aS,4R,5S,6aR)-4-acetoxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester (107796-38-3) → (3aα,4α,5β,6aα)-(-)-hexahydro-4-(phenylcarboxymethyl)-2-oxo-2H-cyclopenta[b]furan-5-yl benzoate

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / NaOMe / methanol

2: 53.1 percent / DMAP / CH₂Cl₂ / 25 °C

With dmap; sodium methylate; In methanol; dichloromethane;

DOI:10.1016/S0968-0896(02)00090-1

upstream raw materials:

formaldehyd

(1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one

acetic anhydride

Downstream raw materials:

<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one

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