ethyl 2β-(ethoxycarbonyl)-5α-(benzyloxy)-6α-hydroxy-3,5,6,6aβ-tetrahydro-2H-cyclopentafuran-2α-acetate

Base Information

• Chemical Name: ethyl 2β-(ethoxycarbonyl)-5α-(benzyloxy)-6α-hydroxy-3,5,6,6aβ-tetrahydro-2H-cyclopentafuran-2α-acetate
• CAS No.: 148145-69-1
• Molecular Formula: C₂₁H₂₄O₈
• Molecular Weight: 404.417

Synonyms:ethyl 2β-(ethoxycarbonyl)-5α-(benzyloxy)-6α-hydroxy-3,5,6,6aβ-tetrahydro-2H-cyclopentafuran-2α-acetate

Chemical Property of ethyl 2β-(ethoxycarbonyl)-5α-(benzyloxy)-6α-hydroxy-3,5,6,6aβ-tetrahydro-2H-cyclopentafuran-2α-acetate

Chemical Property:

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Technology Process of ethyl 2β-(ethoxycarbonyl)-5α-(benzyloxy)-6α-hydroxy-3,5,6,6aβ-tetrahydro-2H-cyclopentafuran-2α-acetate

There total 8 articles about ethyl 2β-(ethoxycarbonyl)-5α-(benzyloxy)-6α-hydroxy-3,5,6,6aβ-tetrahydro-2H-cyclopentafuran-2α-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:

(E)-2-((3S,4R,5R)-3-Benzoyloxy-4,5-dihydroxy-cyclopent-1-enylmethyl)-but-2-enedioic acid diethyl ester → (2R,5S,6S,6aR)-5-Benzoyloxy-2-ethoxycarbonylmethyl-6-hydroxy-3,5,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-carboxylic acid ethyl ester + ethyl 2β-(ethoxycarbonyl)-5α-(benzyloxy)-6α-hydroxy-3,5,6,6aβ-tetrahydro-2H-cyclopentafuran-2α-acetate (148145-69-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Heating;

DOI:10.1021/jm00061a012

Reference yield:

benzoyl chloride (98-88-4) → ethyl 2β-(ethoxycarbonyl)-5α-(benzyloxy)-6α-hydroxy-3,5,6,6aβ-tetrahydro-2H-cyclopentafuran-2α-acetate (148145-69-1)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / 4 h / Ambient temperature

2: 90 percent / Et₂AlI / CH₂Cl₂; toluene / 0.08 h / -78 °C

3: PPh₃, CBr₄ / CH₂Cl₂ / 2 h / Ambient temperature

4: 1) LDA, 2) pyridine / 1) THF, from -78 deg C to RT; 2) benzene, reflux, 2 h

5: 1.0 mM H₂SO₄ / ethanol / 24 h

6: DBU / toluene / 2 h / Heating

With pyridine; carbon tetrabromide; sulfuric acid; diethylaluminum iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; lithium diisopropyl amide; In ethanol; dichloromethane; toluene;

DOI:10.1021/jm00061a012

Reference yield:

(3aR,6aR)-2,2-dimethyl-6-[(trityloxy)methyl]-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one (88559-56-2) → ethyl 2β-(ethoxycarbonyl)-5α-(benzyloxy)-6α-hydroxy-3,5,6,6aβ-tetrahydro-2H-cyclopentafuran-2α-acetate (148145-69-1)

Guidance literature:

Multi-step reaction with 7 steps

1: NaBH₄, CeCl₃*7H₂O / methanol / 3 h / Ambient temperature

2: pyridine / 4 h / Ambient temperature

3: 90 percent / Et₂AlI / CH₂Cl₂; toluene / 0.08 h / -78 °C

4: PPh₃, CBr₄ / CH₂Cl₂ / 2 h / Ambient temperature

5: 1) LDA, 2) pyridine / 1) THF, from -78 deg C to RT; 2) benzene, reflux, 2 h

6: 1.0 mM H₂SO₄ / ethanol / 24 h

7: DBU / toluene / 2 h / Heating

With pyridine; sodium tetrahydroborate; cerium(III) chloride; carbon tetrabromide; sulfuric acid; diethylaluminum iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; lithium diisopropyl amide; In methanol; ethanol; dichloromethane; toluene;

DOI:10.1021/jm00061a012

upstream raw materials:

benzoyl chloride

(3aR,6aR)-2,2-dimethyl-6-[(trityloxy)methyl]-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one

Benzoic acid (3aS,4S,6aR)-6-hydroxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl ester

(3aS,4S,6aR)-2,2-dimethyl-6-[(triphenylmethoxy)methyl]-2H,3aH,4H,6aH-cyclopenta[d][1,3]dioxol-4-ol

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