tert-Butyl-{(S)-2-[(2S,5R,7S)-2-((E)-3-iodo-2-methyl-propenyl)-1,6-dioxa-spiro[4.5]dec-7-yl]-propoxy}-diphenyl-silane

Base Information

Chemical Name:tert-Butyl-{(S)-2-[(2S,5R,7S)-2-((E)-3-iodo-2-methyl-propenyl)-1,6-dioxa-spiro[4.5]dec-7-yl]-propoxy}-diphenyl-silane
CAS No.:858666-95-2
Molecular Formula:C₃₁H₄₃IO₃Si
Molecular Weight:618.671
Hs Code.:

Synonyms:tert-Butyl-{(S)-2-[(2S,5R,7S)-2-((E)-3-iodo-2-methyl-propenyl)-1,6-dioxa-spiro[4.5]dec-7-yl]-propoxy}-diphenyl-silane

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Chemical Property of tert-Butyl-{(S)-2-[(2S,5R,7S)-2-((E)-3-iodo-2-methyl-propenyl)-1,6-dioxa-spiro[4.5]dec-7-yl]-propoxy}-diphenyl-silane

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Technology Process of tert-Butyl-{(S)-2-[(2S,5R,7S)-2-((E)-3-iodo-2-methyl-propenyl)-1,6-dioxa-spiro[4.5]dec-7-yl]-propoxy}-diphenyl-silane

There total 16 articles about tert-Butyl-{(S)-2-[(2S,5R,7S)-2-((E)-3-iodo-2-methyl-propenyl)-1,6-dioxa-spiro[4.5]dec-7-yl]-propoxy}-diphenyl-silane 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:

: 858666-87-2
(2S,5S,7S,1''S)-(+)-2-(1'-benzyloxymethyl)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-1,6-dioxaspiro[4.5]decane

: 858666-95-2
tert-Butyl-{(S)-2-[(2S,5R,7S)-2-((E)-3-iodo-2-methyl-propenyl)-1,6-dioxa-spiro[4.5]dec-7-yl]-propoxy}-diphenyl-silane

Guidance literature:: Multi-step reaction with 6 steps

1: 75 percent / H₂ / Pd/C / ethyl acetate / 4.5 h

2: 95 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

3: 99 percent / CH₂Cl₂ / 20 h / 20 °C

4: 91 percent / di-iso-butylaluminium hydride / CH₂Cl₂; toluene / 0.75 h / -78 °C

5: Et₃N / tetrahydrofuran / 0.33 h / 0 °C

6: 110 mg / NaI / tetrahydrofuran / 2 h / 20 °C

With pyridine; diisobutylaluminum hydride; hydrogen; Dess-Martin periodane; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; 3: Wittig olefination;
DOI:10.1039/b600951d

Reference yield:

: 887001-88-9
(5S,6S)-(+)-5-tert-butyldimethylsilyloxy-7-tert-butyldiphenylsilyloxy-6-methylheptan-1-ol

: 858666-95-2
tert-Butyl-{(S)-2-[(2S,5R,7S)-2-((E)-3-iodo-2-methyl-propenyl)-1,6-dioxa-spiro[4.5]dec-7-yl]-propoxy}-diphenyl-silane

Guidance literature:: Multi-step reaction with 11 steps

1.1: 99 percent / pyridinium chlorochromate; potassium carbonate / CH₂Cl₂ / 3 h / 20 °C

2.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 88 percent / tetrahydrofuran; hexane / 2.5 h / -78 °C

3.1: 93 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 5 h / 20 °C

4.1: 68 percent / Na₂HPO₄; Na/Hg / methanol / 1 h

5.1: 84 percent / p-toluenesulfonic acid monohydrate / toluene / 4 h / 80 °C

6.1: 75 percent / H₂ / Pd/C / ethyl acetate / 4.5 h

7.1: 95 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

8.1: 99 percent / CH₂Cl₂ / 20 h / 20 °C

9.1: 91 percent / di-iso-butylaluminium hydride / CH₂Cl₂; toluene / 0.75 h / -78 °C

10.1: Et₃N / tetrahydrofuran / 0.33 h / 0 °C

11.1: 110 mg / NaI / tetrahydrofuran / 2 h / 20 °C

With pyridine; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; diisobutylaluminum hydride; hydrogen; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; toluene; 8.1: Wittig olefination;
DOI:10.1039/b600951d

Reference yield:

: 858666-74-7
(2'R,3'S,4R,5S)-(+)-3-(7'-benzyloxy-3'-hydroxy-2'-methylheptanoyl)-4-methyl-5-phenyloxazolidin-2-one

: 858666-95-2
tert-Butyl-{(S)-2-[(2S,5R,7S)-2-((E)-3-iodo-2-methyl-propenyl)-1,6-dioxa-spiro[4.5]dec-7-yl]-propoxy}-diphenyl-silane

Guidance literature:: Multi-step reaction with 15 steps

1.1: 87 percent / LiBH₄ / tetrahydrofuran / 0.08 h / 20 °C

2.1: 77 percent / imidazole / CH₂Cl₂ / 20 h / 20 °C

3.1: 95 percent / 4-(dimethylamino)pyridine; 2,6-lutidine / dimethylformamide / 20 h / 20 °C

4.1: 99 percent / H₂ / Pd/C / methanol

5.1: 99 percent / pyridinium chlorochromate; potassium carbonate / CH₂Cl₂ / 3 h / 20 °C

6.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

6.2: 88 percent / tetrahydrofuran; hexane / 2.5 h / -78 °C

7.1: 93 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 5 h / 20 °C

8.1: 68 percent / Na₂HPO₄; Na/Hg / methanol / 1 h

9.1: 84 percent / p-toluenesulfonic acid monohydrate / toluene / 4 h / 80 °C

10.1: 75 percent / H₂ / Pd/C / ethyl acetate / 4.5 h

11.1: 95 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

12.1: 99 percent / CH₂Cl₂ / 20 h / 20 °C

13.1: 91 percent / di-iso-butylaluminium hydride / CH₂Cl₂; toluene / 0.75 h / -78 °C

14.1: Et₃N / tetrahydrofuran / 0.33 h / 0 °C

15.1: 110 mg / NaI / tetrahydrofuran / 2 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; disodium hydrogenphosphate; sodium amalgam; lithium borohydride; n-butyllithium; diisobutylaluminum hydride; hydrogen; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 12.1: Wittig olefination;
DOI:10.1039/b600951d