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

Base Information

• Chemical Name: Benzoic acid (3aS,4S,6aR)-6-hydroxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl ester
• CAS No.: 126261-36-7
• Molecular Formula: C₁₆H₁₈O₅
• Molecular Weight: 290.316

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

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

Chemical Property:

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

There total 4 articles about Benzoic acid (3aS,4S,6aR)-6-hydroxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-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: 90.0%

(1S,2S,3R)-1-benzoyloxy-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopentene → Benzoic acid (3aS,4S,6aR)-6-hydroxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl ester (126261-36-7)

Guidance literature:

With diethylaluminum iodide; In dichloromethane; toluene; at -78 ℃; for 0.0833333h;

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) → Benzoic acid (3aS,4S,6aR)-6-hydroxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl ester (126261-36-7)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; sodium tetrahydroborate; cerium(III) chloride; diethylaluminum iodide; In methanol; dichloromethane; toluene;

DOI:10.1021/jm00061a012

Reference yield:

benzoyl chloride (98-88-4) → Benzoic acid (3aS,4S,6aR)-6-hydroxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl ester (126261-36-7)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 4 h / Ambient temperature

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

With pyridine; diethylaluminum iodide; In 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

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

Downstream raw materials:

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

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