(2S,4S,5R)-4-[(3E,6Z)-(1S,2S,5S)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3,5-dimethyl-2-triethylsilanyloxy-octa-3,6-dienyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

Base Information

Chemical Name:(2S,4S,5R)-4-[(3E,6Z)-(1S,2S,5S)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3,5-dimethyl-2-triethylsilanyloxy-octa-3,6-dienyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane
CAS No.:903558-96-3
Molecular Formula:C₃₅H₆₂O₅Si₂
Molecular Weight:619.045
Hs Code.:

(2S,4S,5R)-4-[(3E,6Z)-(1S,2S,5S)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3,5-dimethyl-2-triethylsilanyloxy-octa-3,6-dienyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

Synonyms:(2S,4S,5R)-4-[(3E,6Z)-(1S,2S,5S)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3,5-dimethyl-2-triethylsilanyloxy-octa-3,6-dienyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

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Chemical Property of (2S,4S,5R)-4-[(3E,6Z)-(1S,2S,5S)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3,5-dimethyl-2-triethylsilanyloxy-octa-3,6-dienyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

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Technology Process of (2S,4S,5R)-4-[(3E,6Z)-(1S,2S,5S)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3,5-dimethyl-2-triethylsilanyloxy-octa-3,6-dienyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

There total 5 articles about (2S,4S,5R)-4-[(3E,6Z)-(1S,2S,5S)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3,5-dimethyl-2-triethylsilanyloxy-octa-3,6-dienyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane 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:

: (E)-(2R,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,4S,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4-dimethyl-5-triethylsilanyloxy-hept-3-enal

: 1530-32-1
ethyltriphenylphosphonium bromide

: 903558-96-3
(2S,4S,5R)-4-[(3E,6Z)-(1S,2S,5S)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3,5-dimethyl-2-triethylsilanyloxy-octa-3,6-dienyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

: (2S,4S,5R)-4-[(3E,6E)-(1S,2S,5S)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3,5-dimethyl-2-triethylsilanyloxy-octa-3,6-dienyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

Guidance literature:: (E)-(2R,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,4S,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4-dimethyl-5-triethylsilanyloxy-hept-3-enal; ethyltriphenylphosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; at 0 ℃;

In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1016/j.tetlet.2006.04.044

Reference yield:

: 903558-95-2
(E)-(2R,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,4S,5R)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2,4-dimethyl-5-triethylsilanyloxy-hept-3-en-1-ol

: 903558-96-3
(2S,4S,5R)-4-[(3E,6Z)-(1S,2S,5S)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3,5-dimethyl-2-triethylsilanyloxy-octa-3,6-dienyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

Guidance literature:: Multi-step reaction with 2 steps

1.1: Dess-Martin reagent; pyridine / CH₂Cl₂ / 0 °C

2.1: t-BuOK / tetrahydrofuran / 0 °C

2.2: tetrahydrofuran / -78 - 20 °C

With pyridine; potassium tert-butylate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 1.1: Dess-Martin oxidation;
DOI:10.1016/j.tetlet.2006.04.044

Reference yield:

: 903558-94-1
(2S,4S,5R)-4-[(E)-(1S,2S,5R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-2-triethylsilanyloxy-hex-3-enyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

: 903558-96-3
(2S,4S,5R)-4-[(3E,6Z)-(1S,2S,5S)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3,5-dimethyl-2-triethylsilanyloxy-octa-3,6-dienyl]-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 74 percent / TBAF; AcOH / tetrahydrofuran / 20 °C

2.1: Dess-Martin reagent; pyridine / CH₂Cl₂ / 0 °C

3.1: t-BuOK / tetrahydrofuran / 0 °C

3.2: tetrahydrofuran / -78 - 20 °C

With pyridine; potassium tert-butylate; tetrabutyl ammonium fluoride; Dess-Martin periodane; acetic acid; In tetrahydrofuran; dichloromethane; 2.1: Dess-Martin oxidation;
DOI:10.1016/j.tetlet.2006.04.044