(1'E,2S,5R,7S,1''S)-(+)-2-(6'-benzyloxy-2'-methyl-1'-hexen-4'-yn-1'-yl)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-1,6-dioxaspiro[4.5]decane

Base Information

Chemical Name:(1'E,2S,5R,7S,1''S)-(+)-2-(6'-benzyloxy-2'-methyl-1'-hexen-4'-yn-1'-yl)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-1,6-dioxaspiro[4.5]decane
CAS No.:858666-63-4
Molecular Formula:C₄₁H₅₂O₄Si
Molecular Weight:636.947
Hs Code.:

Synonyms:(1'E,2S,5R,7S,1''S)-(+)-2-(6'-benzyloxy-2'-methyl-1'-hexen-4'-yn-1'-yl)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-1,6-dioxaspiro[4.5]decane

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Chemical Property of (1'E,2S,5R,7S,1''S)-(+)-2-(6'-benzyloxy-2'-methyl-1'-hexen-4'-yn-1'-yl)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-1,6-dioxaspiro[4.5]decane

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Technology Process of (1'E,2S,5R,7S,1''S)-(+)-2-(6'-benzyloxy-2'-methyl-1'-hexen-4'-yn-1'-yl)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-1,6-dioxaspiro[4.5]decane

There total 16 articles about (1'E,2S,5R,7S,1''S)-(+)-2-(6'-benzyloxy-2'-methyl-1'-hexen-4'-yn-1'-yl)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-1,6-dioxaspiro[4.5]decane 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: 56.0%

: 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

: 4039-82-1
Benzyl propargyl ether

: (1'Z,2S,5R,7S,1''S)-(+)-2-(6'-benzyloxy-2'-methyl-1'-hexen-4'-yn-1'-yl)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-1,6-dioxaspiro[4.5]decane

: 858666-63-4
(1'E,2S,5R,7S,1''S)-(+)-2-(6'-benzyloxy-2'-methyl-1'-hexen-4'-yn-1'-yl)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-1,6-dioxaspiro[4.5]decane

Guidance literature:: Benzyl propargyl ether; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.75h;

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; In tetrahydrofuran; hexane; at -78 - 0 ℃;
DOI:10.1021/ol0507975

Reference yield:

: 858666-69-0
(5S,6S)-(+)-5-tert-butyldimethylsilyloxy-7-tert-butyldiphenylsilyloxy-6-methylheptan-1-al

: 858666-63-4
(1'E,2S,5R,7S,1''S)-(+)-2-(6'-benzyloxy-2'-methyl-1'-hexen-4'-yn-1'-yl)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-1,6-dioxaspiro[4.5]decane

Guidance literature:: Multi-step reaction with 11 steps

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

1.2: 88 percent / tetrahydrofuran; hexane / 2.5 h / -78 °C

2.1: 93 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 5 h / 20 °C

3.1: 68 percent / Na₂HPO₄; Na/Hg / methanol / 1 h

4.1: 84 percent / p-toluenesulfonic acid monohydrate / toluene / 4 h / 80 °C

5.1: 75 percent / H₂ / Pd/C / ethyl acetate / 4.5 h

6.1: 95 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

7.1: 99 percent / CH₂Cl₂ / 20 h / 20 °C

8.1: 91 percent / di-iso-butylaluminium hydride / CH₂Cl₂; toluene / 0.75 h / -78 °C

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

10.1: 110 mg / NaI / tetrahydrofuran / 2 h / 20 °C

11.1: BuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C

11.2: 56 percent / tetrahydrofuran; hexane / 20 h / -78 - 0 °C

With pyridine; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; diisobutylaluminum hydride; hydrogen; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; toluene; 7.1: Wittig olefination;
DOI:10.1039/b600951d

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

: 858666-63-4
(1'E,2S,5R,7S,1''S)-(+)-2-(6'-benzyloxy-2'-methyl-1'-hexen-4'-yn-1'-yl)-7-{2''-(tert-butyldiphenylsilyloxy)-1''-methylethyl}-1,6-dioxaspiro[4.5]decane

Guidance literature:: Multi-step reaction with 7 steps

1.1: 75 percent / H₂ / Pd/C / ethyl acetate / 4.5 h

2.1: 95 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

3.1: 99 percent / CH₂Cl₂ / 20 h / 20 °C

4.1: 91 percent / di-iso-butylaluminium hydride / CH₂Cl₂; toluene / 0.75 h / -78 °C

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

6.1: 110 mg / NaI / tetrahydrofuran / 2 h / 20 °C

7.1: BuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C

7.2: 56 percent / tetrahydrofuran; hexane / 20 h / -78 - 0 °C

With pyridine; n-butyllithium; diisobutylaluminum hydride; hydrogen; Dess-Martin periodane; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; toluene; 3.1: Wittig olefination;
DOI:10.1039/b600951d