(3R,4R)-5,5-bis(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-one

Base Information

Chemical Name:(3R,4R)-5,5-bis(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-one
CAS No.:1355235-05-0
Molecular Formula:C₃₄H₅₄O₈Si₂
Molecular Weight:646.969
Hs Code.:

Synonyms:(3R,4R)-5,5-bis(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-one

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Chemical Property of (3R,4R)-5,5-bis(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-one

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Technology Process of (3R,4R)-5,5-bis(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-one

There total 7 articles about (3R,4R)-5,5-bis(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-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: 94.0%

: 1355235-08-3
(R)-5,5-bis(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)-4-methyldihydrofuran-2(3H)-one

: 333-27-7
methyl trifluoromethanesulfonate

: 1355235-05-0
(3R,4R)-5,5-bis(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-one

Guidance literature:: (R)-5,5-bis(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)-4-methyldihydrofuran-2(3H)-one; With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; at -78 ℃; for 1h;

methyl trifluoromethanesulfonate; In tetrahydrofuran; at -78 ℃; for 4h; diastereoselective reaction;
DOI:10.1021/jo2021696

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1355235-05-0
(3R,4R)-5,5-bis(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C

2.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water; toluene / 2 h / 20 °C

3.1: Celite-supported silver carbonate / toluene / 2 h / 130 °C / Darkness

4.1: n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane / tetrahydrofuran / 1 h / -78 °C

4.2: 4 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo2021696

Reference yield:

: 1276653-04-3
2-(allyloxy)-5-bromo-1,3-dimethoxybenzene

: 1355235-05-0
(3R,4R)-5,5-bis(4-((tert-butyldimethylsilyl)oxy)-3,5-dimethoxyphenyl)-3,4-dimethyldihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 2 h / -78 °C

2.1: 1,3-dimethylbarbituric acid; palladium diacetate; triphenylphosphine / ethanol / 2 h / 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C

4.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water; toluene / 2 h / 20 °C

5.1: Celite-supported silver carbonate / toluene / 2 h / 130 °C / Darkness

6.1: n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane / tetrahydrofuran / 1 h / -78 °C

6.2: 4 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; n-butyllithium; 1,3-dimethylbarbituric acid; palladium diacetate; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; 1,4-dioxane; ethanol; hexane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo2021696