(3R,3aR,4R,5R,6aR)-3,3a,4,5,6,6a-hexahydro-3-[(4-methoxybenzyl)oxy]-4,5-bis(methoxymethoxy)-5-methyl-2H-cyclopenta[b]furan-2-one

Base Information

Chemical Name:(3R,3aR,4R,5R,6aR)-3,3a,4,5,6,6a-hexahydro-3-[(4-methoxybenzyl)oxy]-4,5-bis(methoxymethoxy)-5-methyl-2H-cyclopenta[b]furan-2-one
CAS No.:832078-90-7
Molecular Formula:C₂₀H₂₈O₈
Molecular Weight:396.438
Hs Code.:

Synonyms:(3R,3aR,4R,5R,6aR)-3,3a,4,5,6,6a-hexahydro-3-[(4-methoxybenzyl)oxy]-4,5-bis(methoxymethoxy)-5-methyl-2H-cyclopenta[b]furan-2-one

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Chemical Property of (3R,3aR,4R,5R,6aR)-3,3a,4,5,6,6a-hexahydro-3-[(4-methoxybenzyl)oxy]-4,5-bis(methoxymethoxy)-5-methyl-2H-cyclopenta[b]furan-2-one

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Technology Process of (3R,3aR,4R,5R,6aR)-3,3a,4,5,6,6a-hexahydro-3-[(4-methoxybenzyl)oxy]-4,5-bis(methoxymethoxy)-5-methyl-2H-cyclopenta[b]furan-2-one

There total 19 articles about (3R,3aR,4R,5R,6aR)-3,3a,4,5,6,6a-hexahydro-3-[(4-methoxybenzyl)oxy]-4,5-bis(methoxymethoxy)-5-methyl-2H-cyclopenta[b]furan-2-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: 87.0%

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 832078-89-4
(3R,3aS,4R,5R,6aR)-3,3a,4,5,6,6a-hexahydro-3-hydroxy-4,5-bis(methoxymethoxy)-5-methyl-2H-cyclopenta[b]furan-2-one

: 832078-90-7
(3R,3aR,4R,5R,6aR)-3,3a,4,5,6,6a-hexahydro-3-[(4-methoxybenzyl)oxy]-4,5-bis(methoxymethoxy)-5-methyl-2H-cyclopenta[b]furan-2-one

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 18h;
DOI:10.1055/s-2004-834822

Reference yield:

: 59995-48-1
(R)-4-acetoxycyclopent-2-en-1-one

: 832078-90-7
(3R,3aR,4R,5R,6aR)-3,3a,4,5,6,6a-hexahydro-3-[(4-methoxybenzyl)oxy]-4,5-bis(methoxymethoxy)-5-methyl-2H-cyclopenta[b]furan-2-one

Guidance literature:: Multi-step reaction with 14 steps

1.1: 99 percent / K₂CO₃ / methanol

2.1: 86 percent / Et₃N; DMAP

3.1: 85 percent / toluene / 48 h / Heating

4.1: 80 percent / 18-crown-6; oxone; aq. NaHCO₃ / acetone; CH₂Cl₂ / 2 h / 0 °C

5.1: 81 percent / i-Pr₂NEt / CH₂Cl₂ / 48 h / 20 °C

6.1: 92 percent / pyridine

7.1: 73 percent / TBAF

8.1: 79 percent / CSA

9.1: 89 percent / K₂CO₃ / methanol

10.1: 86 percent / i-Pr₂NEt; NaI / CH₂Cl₂ / 18 h / Heating

11.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C

11.2: 2-benzenesulfonyl-3-(3-nitrophenyl)oxaziridine / tetrahydrofuran; toluene / 0.5 h / -78 °C

11.3: 74 percent / CSA / tetrahydrofuran; toluene / 1 h / -78 - 20 °C

12.1: 87 percent / CSA / CH₂Cl₂ / 18 h / 20 °C

With pyridine; dmap; Oxone; 18-crown-6 ether; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydrogencarbonate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; 4.1: Claisen-Eschenmoser rearrangement;
DOI:10.1055/s-2004-834822

Reference yield:

: 639467-31-5
(1R,4S)-1-[(tert-butyldimethylsilyl)oxy]-4-methylcyclopent-2-en-4-ol

: 832078-90-7
(3R,3aR,4R,5R,6aR)-3,3a,4,5,6,6a-hexahydro-3-[(4-methoxybenzyl)oxy]-4,5-bis(methoxymethoxy)-5-methyl-2H-cyclopenta[b]furan-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 85 percent / toluene / 48 h / Heating

2.1: 80 percent / 18-crown-6; NaHCO₃; potassium peroxymonosulfate / CH₂Cl₂; acetone; H₂O / 2 h / 0 °C

3.1: 81 percent / diisopropylethylamine / CH₂Cl₂ / 48 h / 20 °C

4.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / 20 °C

5.1: 86 percent / diisopropylethylamine; NaI / CH₂Cl₂ / 18 h / Heating

6.1: potassium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

6.2: 3-(3-nitrophenyl)-2-(phenylsulfonyl)-1,2-oxaziridine / tetrahydrofuran / 0.5 h / -78 °C

6.3: 74 percent / chlorosulfonic acid / tetrahydrofuran / 1 h / -78 - 20 °C

7.1: 87 percent / chlorosulfonic acid / CH₂Cl₂ / 18 h / 20 °C

With chlorosulfonic acid; Oxone; potassium hexamethyldisilazane; 18-crown-6 ether; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; sodium iodide; In tetrahydrofuran; dichloromethane; water; acetone; toluene;
DOI:10.1002/hlca.200590124