(2S,3R)-1-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-2-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-hex-5-en-3-ol

Base Information

Chemical Name:(2S,3R)-1-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-2-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-hex-5-en-3-ol
CAS No.:871912-53-7
Molecular Formula:C₃₅H₄₄O₅Si
Molecular Weight:572.817
Hs Code.:

Synonyms:(2S,3R)-1-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-2-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-hex-5-en-3-ol

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Chemical Property of (2S,3R)-1-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-2-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-hex-5-en-3-ol

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Technology Process of (2S,3R)-1-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-2-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-hex-5-en-3-ol

There total 9 articles about (2S,3R)-1-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-2-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-hex-5-en-3-ol 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%

: 871912-62-8
(2S,3R)-5-Methyl-2-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-hex-5-ene-1,3-diol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 871912-53-7
(2S,3R)-1-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-2-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-hex-5-en-3-ol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 23 ℃; for 0.5h;
DOI:10.1016/j.tetlet.2005.09.164

Reference yield:

: (2R,4R,5R)-5-((1R,2R)-1-Formyl-2-hydroxy-4-methyl-pent-4-enyloxy)-2-phenyl-[1,3]dioxane-4-carbaldehyde

: 871912-53-7
(2S,3R)-1-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-2-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-hex-5-en-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaBH₄ / methanol / 1 h / 0 °C

2.1: 100 percent / benzene / 0.5 h / 23 °C

3.1: DMPI / CH₂Cl₂ / 21 h / 23 °C

4.1: NHMDS / tetrahydrofuran / 1 h / 23 °C

4.2: tetrahydrofuran / 2 h / -78 - 23 °C

5.1: H₂O₂ / ethyl acetate / 1 h / 23 °C

6.1: 90 percent / imidazole / dimethylformamide / 0.5 h / 23 °C

With 1H-imidazole; sodium tetrahydroborate; dimethyl pimelimidate dihydrochloride; dihydrogen peroxide; sodium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene; 3.1: Dess-Martin oxidation / 4.1: Wittig reaction;
DOI:10.1016/j.tetlet.2005.09.164

Reference yield:

: (2R,4aR,6S,8aS)-6-((R)-1-Hydroxy-3-methyl-but-3-enyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

: 871912-53-7
(2S,3R)-1-(tert-Butyl-diphenyl-silanyloxy)-5-methyl-2-((2R,4S,5R)-2-phenyl-4-vinyl-[1,3]dioxan-5-yloxy)-hex-5-en-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaIO₄ / dioxane; H₂O / 1 h / 23 °C

2.1: NaBH₄ / methanol / 1 h / 0 °C

3.1: 100 percent / benzene / 0.5 h / 23 °C

4.1: DMPI / CH₂Cl₂ / 21 h / 23 °C

5.1: NHMDS / tetrahydrofuran / 1 h / 23 °C

5.2: tetrahydrofuran / 2 h / -78 - 23 °C

6.1: H₂O₂ / ethyl acetate / 1 h / 23 °C

7.1: 90 percent / imidazole / dimethylformamide / 0.5 h / 23 °C

With 1H-imidazole; sodium tetrahydroborate; sodium periodate; dimethyl pimelimidate dihydrochloride; dihydrogen peroxide; sodium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; benzene; 4.1: Dess-Martin oxidation / 5.1: Wittig reaction;
DOI:10.1016/j.tetlet.2005.09.164