(3aR,4S,6aS)-4-Benzyloxy-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxole

Base Information

Chemical Name:(3aR,4S,6aS)-4-Benzyloxy-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxole
CAS No.:869711-12-6
Molecular Formula:C₁₅H₁₈O₃
Molecular Weight:246.306
Hs Code.:

Synonyms:(3aR,4S,6aS)-4-Benzyloxy-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxole

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Chemical Property of (3aR,4S,6aS)-4-Benzyloxy-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxole

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Technology Process of (3aR,4S,6aS)-4-Benzyloxy-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxole

There total 7 articles about (3aR,4S,6aS)-4-Benzyloxy-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxole 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: 97.0%

: 100-39-0
benzyl bromide

: 369647-29-0
(3aR,4S,6aS)-2,2-dimethyl-2H,3aH,4H,6aH-cyclopenta[d][1,3]-dioxol-4-ol

: 869711-12-6
(3aR,4S,6aS)-4-Benzyloxy-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxole

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2005.08.163

Reference yield:

: 869711-30-8
Acetic acid (3aS,4R,6S,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester

: 869711-12-6
(3aR,4S,6aS)-4-Benzyloxy-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxole

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / NH₃ / methanol

2: 93 percent / TPP; DIAD / toluene / 80 °C

3: 95 percent / TBAF / tetrahydrofuran

4: 97 percent / NaH / dimethylformamide

With di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; ammonia; thiamine diphosphate; sodium hydride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; 2: Mitsunobu-type elimination;
DOI:10.1016/j.tetlet.2005.08.163

Reference yield:

: 60410-16-4
(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate

: 869711-12-6
(3aR,4S,6aS)-4-Benzyloxy-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxole

Guidance literature:: Multi-step reaction with 7 steps

1: 91 percent / imidazole / CH₂Cl₂

2: OsO₄; NMO / acetone; H₂O

3: pTSA / acetone

4: 85 percent / NH₃ / methanol

5: 93 percent / TPP; DIAD / toluene / 80 °C

6: 95 percent / TBAF / tetrahydrofuran

7: 97 percent / NaH / dimethylformamide

With 1H-imidazole; osmium(VIII) oxide; N-methyl-2-indolinone; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; ammonia; thiamine diphosphate; sodium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 5: Mitsunobu-type elimination;
DOI:10.1016/j.tetlet.2005.08.163