(R)-2-(4-methoxybenzyloxy)-2-[(1R,2R,3R,5R)-5-hydroxy-2,3-bis(methoxymethoxy)-3-methylcyclopentyl]-1-(pyrrolidin-1-yl)ethanone

Base Information

Chemical Name:(R)-2-(4-methoxybenzyloxy)-2-[(1R,2R,3R,5R)-5-hydroxy-2,3-bis(methoxymethoxy)-3-methylcyclopentyl]-1-(pyrrolidin-1-yl)ethanone
CAS No.:832078-91-8
Molecular Formula:C₂₄H₃₇NO₈
Molecular Weight:467.56
Hs Code.:

Synonyms:(R)-2-(4-methoxybenzyloxy)-2-[(1R,2R,3R,5R)-5-hydroxy-2,3-bis(methoxymethoxy)-3-methylcyclopentyl]-1-(pyrrolidin-1-yl)ethanone

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Chemical Property of (R)-2-(4-methoxybenzyloxy)-2-[(1R,2R,3R,5R)-5-hydroxy-2,3-bis(methoxymethoxy)-3-methylcyclopentyl]-1-(pyrrolidin-1-yl)ethanone

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Technology Process of (R)-2-(4-methoxybenzyloxy)-2-[(1R,2R,3R,5R)-5-hydroxy-2,3-bis(methoxymethoxy)-3-methylcyclopentyl]-1-(pyrrolidin-1-yl)ethanone

There total 20 articles about (R)-2-(4-methoxybenzyloxy)-2-[(1R,2R,3R,5R)-5-hydroxy-2,3-bis(methoxymethoxy)-3-methylcyclopentyl]-1-(pyrrolidin-1-yl)ethanone 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: 91.0%

: 123-75-1
pyrrolidine

: 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

: 832078-91-8
(R)-2-(4-methoxybenzyloxy)-2-[(1R,2R,3R,5R)-5-hydroxy-2,3-bis(methoxymethoxy)-3-methylcyclopentyl]-1-(pyrrolidin-1-yl)ethanone

Guidance literature:: In toluene; for 18h; Heating;
DOI:10.1055/s-2004-834822 DOI:10.1002/hlca.200590124

Reference yield:

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

: 832078-91-8
(R)-2-(4-methoxybenzyloxy)-2-[(1R,2R,3R,5R)-5-hydroxy-2,3-bis(methoxymethoxy)-3-methylcyclopentyl]-1-(pyrrolidin-1-yl)ethanone

Guidance literature:: Multi-step reaction with 15 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

13.1: 91 percent / toluene / 18 h / Heating

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:

: 832078-84-9
2-[(1S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}3-mehylcyclopent-2-en-1-yl]-N,N-dimethylacetamide

: 832078-91-8
(R)-2-(4-methoxybenzyloxy)-2-[(1R,2R,3R,5R)-5-hydroxy-2,3-bis(methoxymethoxy)-3-methylcyclopentyl]-1-(pyrrolidin-1-yl)ethanone

Guidance literature:: Multi-step reaction with 7 steps

1.1: 80 percent / 18-crown-6; NaHCO₃; potassium peroxymonosulfate / CH₂Cl₂; acetone; H₂O / 2 h / 0 °C

2.1: 81 percent / diisopropylethylamine / CH₂Cl₂ / 48 h / 20 °C

3.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / 20 °C

4.1: 86 percent / diisopropylethylamine; NaI / CH₂Cl₂ / 18 h / Heating

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

5.2: 3-(3-nitrophenyl)-2-(phenylsulfonyl)-1,2-oxaziridine / tetrahydrofuran / 0.5 h / -78 °C

5.3: 74 percent / chlorosulfonic acid / tetrahydrofuran / 1 h / -78 - 20 °C

6.1: 87 percent / chlorosulfonic acid / CH₂Cl₂ / 18 h / 20 °C

7.1: 91 percent / toluene / 18 h / Heating

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