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

Base Information

Chemical Name: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
CAS No.:275356-05-3
Molecular Formula:C₃₇H₆₀O₇Si
Molecular Weight:644.965
Hs Code.:

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

Synonyms: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

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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]-3-(4-methoxy-benzyloxy)-2,4-dimethyl-5-triisopropylsilanyloxy-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]-3-(4-methoxy-benzyloxy)-2,4-dimethyl-5-triisopropylsilanyloxy-pentyl ester

There total 4 articles about 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 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: 94.0%

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

: 275355-98-1
Acetic acid (1S,2R,3R,4R)-1-[(S)-1-(6-ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-ethyl]-3-hydroxy-2,4-dimethyl-5-triisopropylsilanyloxy-pentyl ester

: 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

Guidance literature:: trifluorormethanesulfonic acid; In diethyl ether;
DOI:10.1021/ol000027n

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

: (R)-2-(6-Ethyl-3,5-dimethyl-4-oxo-4H-pyran-2-yl)-propionaldehyde

: 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

Guidance literature:: Multi-step reaction with 3 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

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