((2S,3R)-3-Benzyloxymethyl-3-methyl-oxiranyl)-[(R)-2-(3,4-dimethoxy-benzyloxymethyl)-6-hydroxy-3,3-dimethyl-cyclohex-1-enyl]-methanone

Base Information

Chemical Name:((2S,3R)-3-Benzyloxymethyl-3-methyl-oxiranyl)-[(R)-2-(3,4-dimethoxy-benzyloxymethyl)-6-hydroxy-3,3-dimethyl-cyclohex-1-enyl]-methanone
CAS No.:1027739-76-9
Molecular Formula:C₃₀H₃₈O₇
Molecular Weight:510.628
Hs Code.:

Synonyms:((2S,3R)-3-Benzyloxymethyl-3-methyl-oxiranyl)-[(R)-2-(3,4-dimethoxy-benzyloxymethyl)-6-hydroxy-3,3-dimethyl-cyclohex-1-enyl]-methanone

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Chemical Property of ((2S,3R)-3-Benzyloxymethyl-3-methyl-oxiranyl)-[(R)-2-(3,4-dimethoxy-benzyloxymethyl)-6-hydroxy-3,3-dimethyl-cyclohex-1-enyl]-methanone

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Technology Process of ((2S,3R)-3-Benzyloxymethyl-3-methyl-oxiranyl)-[(R)-2-(3,4-dimethoxy-benzyloxymethyl)-6-hydroxy-3,3-dimethyl-cyclohex-1-enyl]-methanone

There total 17 articles about ((2S,3R)-3-Benzyloxymethyl-3-methyl-oxiranyl)-[(R)-2-(3,4-dimethoxy-benzyloxymethyl)-6-hydroxy-3,3-dimethyl-cyclohex-1-enyl]-methanone 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: 90.0%

: 444809-23-8
((2S,3R)-3-Benzyloxymethyl-3-methyl-oxiranyl)-[(R)-6-(tert-butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxymethyl)-3,3-dimethyl-cyclohex-1-enyl]-methanone

: 1027739-76-9
((2S,3R)-3-Benzyloxymethyl-3-methyl-oxiranyl)-[(R)-2-(3,4-dimethoxy-benzyloxymethyl)-6-hydroxy-3,3-dimethyl-cyclohex-1-enyl]-methanone

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1021/ol026159t

Reference yield:

: 21852-32-4
4-bromomethyl-1,2-dimethoxybenzene

: 1027739-76-9
((2S,3R)-3-Benzyloxymethyl-3-methyl-oxiranyl)-[(R)-2-(3,4-dimethoxy-benzyloxymethyl)-6-hydroxy-3,3-dimethyl-cyclohex-1-enyl]-methanone

Guidance literature:: Multi-step reaction with 4 steps

1.1: 95 percent / NaH / tetrahydrofuran / 8 h / 20 °C

2.1: t-BuLi / diethyl ether / 0.5 h / -78 °C

2.2: 60 percent / TMEDA / 0.5 h / -78 °C

3.1: 90 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

4.1: 90 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

With tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ol026159t

Reference yield:

: 6553-64-6
6,6-Dimethyl-2-cyclohexen-1-one

: 1027739-76-9
((2S,3R)-3-Benzyloxymethyl-3-methyl-oxiranyl)-[(R)-2-(3,4-dimethoxy-benzyloxymethyl)-6-hydroxy-3,3-dimethyl-cyclohex-1-enyl]-methanone

Guidance literature:: Multi-step reaction with 10 steps

1.1: 78 percent / n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

2.1: 90 percent / PCC / CH₂Cl₂ / 12 h / 20 °C

3.1: 60 percent / pyridinium tribromide; pyridine / CH₂Cl₂ / 20 h / 20 - 40 °C

4.1: 92 percent / (S)-CBS; BH₃*THF / tetrahydrofuran / 2 h / 20 °C

5.1: 85 percent / imidazole / dimethylformamide / 2 h / 20 - 40 °C

6.1: 70 percent / MgBr₂*Et₂O; BuSH / diethyl ether / 12 h / 20 °C

7.1: 95 percent / NaH / tetrahydrofuran / 8 h / 20 °C

8.1: t-BuLi / diethyl ether / 0.5 h / -78 °C

8.2: 60 percent / TMEDA / 0.5 h / -78 °C

9.1: 90 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 20 °C

10.1: 90 percent / TBAF / tetrahydrofuran / 0.5 h / 0 °C

With pyridine; 1H-imidazole; n-butyllithium; borane-THF; (S)-diphenylprolinol; n-butanethiol; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; pyridinium hydrobromide perbromide; pyridinium chlorochromate; magnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol026159t