(2R,3S,4S,5S)-2-tert-butyldiphenylsilyloxymethyl-3-ethenyl-4,7,7-trimethyl-1,6-dioxaspiro[4.4]nonane

Base Information

Chemical Name:(2R,3S,4S,5S)-2-tert-butyldiphenylsilyloxymethyl-3-ethenyl-4,7,7-trimethyl-1,6-dioxaspiro[4.4]nonane
CAS No.:937068-08-1
Molecular Formula:C₂₉H₄₀O₃Si
Molecular Weight:464.72
Hs Code.:

Synonyms:(2R,3S,4S,5S)-2-tert-butyldiphenylsilyloxymethyl-3-ethenyl-4,7,7-trimethyl-1,6-dioxaspiro[4.4]nonane

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3S,4S,5S)-2-tert-butyldiphenylsilyloxymethyl-3-ethenyl-4,7,7-trimethyl-1,6-dioxaspiro[4.4]nonane

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Technology Process of (2R,3S,4S,5S)-2-tert-butyldiphenylsilyloxymethyl-3-ethenyl-4,7,7-trimethyl-1,6-dioxaspiro[4.4]nonane

There total 10 articles about (2R,3S,4S,5S)-2-tert-butyldiphenylsilyloxymethyl-3-ethenyl-4,7,7-trimethyl-1,6-dioxaspiro[4.4]nonane 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: 74.0%

: 937067-92-0
(3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-(triethylsilyloxy)ethyl)-4,8-dimethyl-8-(triethylsilyloxy)-1-nonen-5-one

: 937068-08-1
(2R,3S,4S,5S)-2-tert-butyldiphenylsilyloxymethyl-3-ethenyl-4,7,7-trimethyl-1,6-dioxaspiro[4.4]nonane

: (2R,3S,4S,5R)-2-tert-butyldiphenylsilyloxymethyl-3-ethenyl-4,7,7-trimethyl-1,6-dioxaspiro[4.4]nonane

: 937068-12-7
(2R,3S,4R,5R)-2-tert-butyldiphenylsilyloxymethyl-3-ethenyl-4,7,7-trimethyl-1,6-dioxaspiro[4.4]nonane

: 937068-14-9
(2R,3S,4R,5S)-2-tert-butyldiphenylsilyloxymethyl-3-ethenyl-4,7,7-trimethyl-1,6-dioxaspiro[4.4]nonane

Guidance literature:: (3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-(triethylsilyloxy)ethyl)-4,8-dimethyl-8-(triethylsilyloxy)-1-nonen-5-one; With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 3h;

With pyridinium p-toluenesulfonate; In dichloromethane; at 80 ℃; for 5h; Further stages.;
DOI:10.1021/jo0626461

Reference yield: 62.0%

: (2R,3S,4R)-2-tert-butyldiphenylsilyloxymethyl-3-ethenyl-4,7,7-trimethyl-1,6-dioxaspiro[4.4]nonane

: 937068-08-1
(2R,3S,4S,5S)-2-tert-butyldiphenylsilyloxymethyl-3-ethenyl-4,7,7-trimethyl-1,6-dioxaspiro[4.4]nonane

: (2R,3S,4S,5R)-2-tert-butyldiphenylsilyloxymethyl-3-ethenyl-4,7,7-trimethyl-1,6-dioxaspiro[4.4]nonane

Guidance literature:: With pyridinium p-toluenesulfonate; In dichloromethane; at 80 ℃;
DOI:10.1021/jo0626461

Reference yield:

: 937067-97-5
(3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2-methyl-4-pentenenitrile

: 937068-08-1
(2R,3S,4S,5S)-2-tert-butyldiphenylsilyloxymethyl-3-ethenyl-4,7,7-trimethyl-1,6-dioxaspiro[4.4]nonane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / pyridine; DMAP / 20 h / 20 °C

2.1: 86 percent / Dibal / toluene / 2.5 h / -78 - -5 °C

3.1: iodine; magnesium / tetrahydrofuran / 2.5 h / 20 °C

3.2: tetrahydrofuran / 0.25 h / 0 °C

4.1: 1.54 g / Dess-Martin reagent / CH₂Cl₂ / 2 h / 20 °C

5.1: aq. HCl / tetrahydrofuran / 3 h / 20 °C

5.2: 74 percent / PPTS / CH₂Cl₂ / 5 h / 80 °C

With pyridine; hydrogenchloride; dmap; iodine; diisobutylaluminium hydride; Dess-Martin periodane; magnesium; In tetrahydrofuran; dichloromethane; toluene; 3.2: Grignard addition;
DOI:10.1021/jo0626461