(3S,4R,5R)-5-(benzyloxymethyl)-3,4-(cyclohexylidenedioxy)-5-ethoxy-4,5-dihydrofuran-2(3H)-one

Base Information

• Chemical Name: (3S,4R,5R)-5-(benzyloxymethyl)-3,4-(cyclohexylidenedioxy)-5-ethoxy-4,5-dihydrofuran-2(3H)-one
• CAS No.: 288103-09-3
• Molecular Formula: C₂₀H₂₆O₆
• Molecular Weight: 362.423

Synonyms:(3S,4R,5R)-5-(benzyloxymethyl)-3,4-(cyclohexylidenedioxy)-5-ethoxy-4,5-dihydrofuran-2(3H)-one

Chemical Property of (3S,4R,5R)-5-(benzyloxymethyl)-3,4-(cyclohexylidenedioxy)-5-ethoxy-4,5-dihydrofuran-2(3H)-one

Chemical Property:

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Technology Process of (3S,4R,5R)-5-(benzyloxymethyl)-3,4-(cyclohexylidenedioxy)-5-ethoxy-4,5-dihydrofuran-2(3H)-one

There total 2 articles about (3S,4R,5R)-5-(benzyloxymethyl)-3,4-(cyclohexylidenedioxy)-5-ethoxy-4,5-dihydrofuran-2(3H)-one 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%

cycloxexanone dimethyl ketal (933-40-4) + (3S,4R,5R)-5-benzyloxymethyl-5-ethoxy-3,4-dihydroxy-dihydro-furan-2-one (288103-14-0) → (3S,4R,5R)-5-(benzyloxymethyl)-3,4-(cyclohexylidenedioxy)-5-ethoxy-4,5-dihydrofuran-2(3H)-one (288103-09-3)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 0.5h; Heating;

DOI:10.1021/jo000154x

Reference yield:

(-)-5-(benzyloxymethyl)-5-ethoxy-5H-furan-2-one (288103-07-1) → (3S,4R,5R)-5-(benzyloxymethyl)-3,4-(cyclohexylidenedioxy)-5-ethoxy-4,5-dihydrofuran-2(3H)-one (288103-09-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 percent / KMnO₄; cis-dicyclohexano-18-crown-6 / CH₂Cl₂ / 2.5 h / -40 °C

2: 86 percent / TsOH / benzene / 0.5 h / Heating

With potassium permanganate; dicyclohexano-18-crown-6; toluene-4-sulfonic acid; In dichloromethane; benzene; 1: Oxidation / 2: Condensation;

DOI:10.1021/jo000154x

Reference yield: 52.0%

(3S,4R,5R)-5-(benzyloxymethyl)-3,4-(cyclohexylidenedioxy)-5-ethoxy-4,5-dihydrofuran-2(3H)-one (288103-09-3) + dimethyl methane phosphonate (756-79-6) → (4S,5S)-3-benzyloxymethyl-4,5-O-cyclohexylidene-cyclopent-2-enone (288103-10-6)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 2.5h;

DOI:10.1021/jo000154x

upstream raw materials:

cycloxexanone dimethyl ketal

(3S,4R,5R)-5-benzyloxymethyl-5-ethoxy-3,4-dihydroxy-dihydro-furan-2-one

(-)-5-(benzyloxymethyl)-5-ethoxy-5H-furan-2-one

Downstream raw materials:

(4S,5S)-3-benzyloxymethyl-4,5-O-cyclohexylidene-cyclopent-2-enone

(1R,4S,5R)-3-benzyloxymethyl-4,5-O-cyclohexylidene-cyclopent-2-enol

(1R,4S,5R)-methanesulfonic acid 3-benzyloxymethyl-4,5-O-cyclohexylidene-cyclopent-2-enyl ester

(1S,4S,5R)-9-(3-benzyloxymethyl-4,5-O-cyclohexylidene-cyclopent-2-enyl)9H-purin-6-ylamine

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