Acetic acid (1S,2R,3R,4R)-1-[(S)-1-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-ethyl]-5-hydroxy-3-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl ester

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Chemical Name:Acetic acid (1S,2R,3R,4R)-1-[(S)-1-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-ethyl]-5-hydroxy-3-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl ester
CAS No.:275356-06-4
Molecular Formula:C₂₈H₄₀O₇
Molecular Weight:488.621
Hs Code.:

Synonyms:Acetic acid (1S,2R,3R,4R)-1-[(S)-1-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-ethyl]-5-hydroxy-3-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl ester

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Chemical Property of Acetic acid (1S,2R,3R,4R)-1-[(S)-1-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-ethyl]-5-hydroxy-3-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl ester

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Technology Process of Acetic acid (1S,2R,3R,4R)-1-[(S)-1-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-ethyl]-5-hydroxy-3-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl ester

There total 6 articles about Acetic acid (1S,2R,3R,4R)-1-[(S)-1-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-ethyl]-5-hydroxy-3-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl 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: 87.0%

: 275356-05-3
Acetic acid (1S,2R,3R,4R)-1-[(S)-1-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-ethyl]-3-(4-methoxy-benzyloxy)-2,4-dimethyl-5-triisopropylsilanyloxy-pentyl ester

: 275356-06-4
Acetic acid (1S,2R,3R,4R)-1-[(S)-1-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-ethyl]-5-hydroxy-3-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1021/ol000027n

Reference yield:

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

: 275356-06-4
Acetic acid (1S,2R,3R,4R)-1-[(S)-1-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-ethyl]-5-hydroxy-3-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / TfOH / diethyl ether

2: 87 percent / TBAF / tetrahydrofuran

With tetrabutyl ammonium fluoride; trifluorormethanesulfonic acid; In tetrahydrofuran; diethyl ether; 1: Etherification / 2: desilylation;
DOI:10.1021/ol000027n

Reference yield:

: 143627-33-2
(R)-2-Methyl-1-triisopropylsilanyloxy-pentan-3-one

: 275356-06-4
Acetic acid (1S,2R,3R,4R)-1-[(S)-1-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-ethyl]-5-hydroxy-3-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: Sn(OTf)2; Et₃N / CH₂Cl₂ / 3 h / -78 °C

1.2: 74 percent / CH₂Cl₂ / 1.5 h / -78 °C

2.1: 100 percent / SmI₂ / tetrahydrofuran / 16 h / -26 °C

3.1: 94 percent / TfOH / diethyl ether

4.1: 87 percent / TBAF / tetrahydrofuran

With tin(II) trifluoromethanesulfonate; samarium diiodide; tetrabutyl ammonium fluoride; triethylamine; trifluorormethanesulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: enolization / 1.2: Addition / 2.1: Acetylation / 3.1: Etherification / 4.1: desilylation;
DOI:10.1021/ol000027n