(4R,5S,6S)-2-[(4S,5R)-5-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-5-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-8-en-3-one

Base Information

Chemical Name:(4R,5S,6S)-2-[(4S,5R)-5-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-5-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-8-en-3-one
CAS No.:245040-43-1
Molecular Formula:C₃₂H₅₂O₅Si
Molecular Weight:544.847
Hs Code.:

Synonyms:(4R,5S,6S)-2-[(4S,5R)-5-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-5-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-8-en-3-one

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Chemical Property of (4R,5S,6S)-2-[(4S,5R)-5-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-5-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-8-en-3-one

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Technology Process of (4R,5S,6S)-2-[(4S,5R)-5-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-5-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-8-en-3-one

There total 8 articles about (4R,5S,6S)-2-[(4S,5R)-5-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-5-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-8-en-3-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: 92.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 245040-57-7
(4R,5S,6S)-2-[(4S,5R)-5-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-5-hydroxy-2,4,6-trimethyl-non-8-en-3-one

: 245040-43-1
(4R,5S,6S)-2-[(4S,5R)-5-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-5-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-8-en-3-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 - 25 ℃; for 3h;
DOI:10.1016/S0040-4020(99)00301-4

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 245040-43-1
(4R,5S,6S)-2-[(4S,5R)-5-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-5-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-8-en-3-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: camphosulfonic acid / CH₂Cl₂ / 1 h / -78 °C

1.2: 55 percent / Dess-Martin periodinane reagent / CH₂Cl₂ / 2 h / 0 - 25 °C

2.1: 62 percent / iPr₂NH; nBuLi / tetrahydrofuran / 0.33 h / -78 °C

3.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -78 - 25 °C

With 2,6-dimethylpyridine; n-butyllithium; camphor-10-sulfonic acid; diisopropylamine; In tetrahydrofuran; dichloromethane; 1.1: Condensation / 1.2: Oxidation / 2.1: Condensation / 3.1: Silylation;
DOI:10.1016/S0040-4020(99)00301-4

Reference yield:

: 128461-58-5
(4S,5R)-4-Methyl-3-(pent-4-enoyl)-5-phenyl-1,3-oxazolidin-2-one

: 245040-43-1
(4R,5S,6S)-2-[(4S,5R)-5-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-5-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-8-en-3-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 0 °C

1.2: 49 percent / CH₂Cl₂ / 3 h / -78 - 0 °C

2.1: 63 percent / LiBH₄; H₂O / diethyl ether; tetrahydrofuran / 4 h / 0 - 25 °C

3.1: camphosulfonic acid / CH₂Cl₂ / 1 h / -78 °C

3.2: 55 percent / Dess-Martin periodinane reagent / CH₂Cl₂ / 2 h / 0 - 25 °C

4.1: 62 percent / iPr₂NH; nBuLi / tetrahydrofuran / 0.33 h / -78 °C

5.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -78 - 25 °C

With 2,6-dimethylpyridine; lithium borohydride; n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; water; triethylamine; diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: addition / 1.2: Condensation / 2.1: Reduction / 3.1: Condensation / 3.2: Oxidation / 4.1: Condensation / 5.1: Silylation;
DOI:10.1016/S0040-4020(99)00301-4