3-[(2R,4S)-5-Hydroxy-1-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl]-4-methoxy-5-methylene-5H-furan-2-one

Base Information

Chemical Name:3-[(2R,4S)-5-Hydroxy-1-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl]-4-methoxy-5-methylene-5H-furan-2-one
CAS No.:897014-71-0
Molecular Formula:C₂₁H₂₈O₆
Molecular Weight:376.45
Hs Code.:

Synonyms:3-[(2R,4S)-5-Hydroxy-1-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl]-4-methoxy-5-methylene-5H-furan-2-one

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Chemical Property of 3-[(2R,4S)-5-Hydroxy-1-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl]-4-methoxy-5-methylene-5H-furan-2-one

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Technology Process of 3-[(2R,4S)-5-Hydroxy-1-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl]-4-methoxy-5-methylene-5H-furan-2-one

There total 4 articles about 3-[(2R,4S)-5-Hydroxy-1-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl]-4-methoxy-5-methylene-5H-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: 81.0%

: 897014-78-7
Acetic acid (2S,4R)-5-(4-methoxy-benzyloxy)-5-(4-methoxy-5-methylene-2-oxo-2,5-dihydro-furan-3-yl)-2,4-dimethyl-pentyl ester

: 897014-71-0
3-[(2R,4S)-5-Hydroxy-1-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl]-4-methoxy-5-methylene-5H-furan-2-one

Guidance literature:: With sodium phosphate buffer; Amano Lipase AK; In acetonitrile; at 20 ℃; for 12h; pH=6.2;
DOI:10.1016/j.tet.2006.01.106

Reference yield:

: 897014-69-6
Acetic acid (2S,4R)-5-hydroxy-5-(4-methoxy-5-methylene-2-oxo-2,5-dihydro-furan-3-yl)-2,4-dimethyl-pentyl ester

: 897014-71-0
3-[(2R,4S)-5-Hydroxy-1-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl]-4-methoxy-5-methylene-5H-furan-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / (+/-)-camphorsulfonic acid / CH₂Cl₂; cyclohexane / 7 h / 0 - 20 °C

2: 81 percent / Amano lipase AK; sodium phosphate buffer / acetonitrile / 12 h / 20 °C / pH 6.2

With sodium phosphate buffer; Amano Lipase AK; camphor-10-sulfonic acid; In dichloromethane; cyclohexane; acetonitrile;
DOI:10.1016/j.tet.2006.01.106

Reference yield:

: 90270-02-3,97937-36-5
(2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate

: 897014-71-0
3-[(2R,4S)-5-Hydroxy-1-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl]-4-methoxy-5-methylene-5H-furan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: oxalyl chloride; Et₃N; DMSO / CH₂Cl₂ / 1.5 h / -78 - 20 °C

2.1: LDA / tetrahydrofuran / 0.1 h / -100 °C

2.2: 58 percent / tetrahydrofuran / 0.25 h / -100 - -90 °C

3.1: 98 percent / (+/-)-camphorsulfonic acid / CH₂Cl₂; cyclohexane / 7 h / 0 - 20 °C

4.1: 81 percent / Amano lipase AK; sodium phosphate buffer / acetonitrile / 12 h / 20 °C / pH 6.2

With oxalyl dichloride; sodium phosphate buffer; Amano Lipase AK; camphor-10-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; cyclohexane; acetonitrile; 1.1: Swern oxidation;
DOI:10.1016/j.tet.2006.01.106