(3R)-3-hydroxy-4-{(4S,6R)-2-(4-methoxyphenyl)-6-[2-(pivaloyloxy)ethyl]-1,3-dioxan-4-yl}butyl pivalate

Base Information

Chemical Name:(3R)-3-hydroxy-4-{(4S,6R)-2-(4-methoxyphenyl)-6-[2-(pivaloyloxy)ethyl]-1,3-dioxan-4-yl}butyl pivalate
CAS No.:1372869-91-4
Molecular Formula:C₂₇H₄₂O₈
Molecular Weight:494.626
Hs Code.:

Synonyms:

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Chemical Property of (3R)-3-hydroxy-4-{(4S,6R)-2-(4-methoxyphenyl)-6-[2-(pivaloyloxy)ethyl]-1,3-dioxan-4-yl}butyl pivalate

Chemical Property:

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Technology Process of (3R)-3-hydroxy-4-{(4S,6R)-2-(4-methoxyphenyl)-6-[2-(pivaloyloxy)ethyl]-1,3-dioxan-4-yl}butyl pivalate

There total 10 articles about (3R)-3-hydroxy-4-{(4S,6R)-2-(4-methoxyphenyl)-6-[2-(pivaloyloxy)ethyl]-1,3-dioxan-4-yl}butyl pivalate 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:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 1372869-90-3
(3R,7R)-3,5,7-trihydroxynonane-1,9-diyl bis(2,2-dimethylpropanoate)

: 1372870-09-1
(3R)-3-hydroxy-4-{(4R,6R)-2-(4-methoxyphenyl)-6-[2-(pivaloyloxy)ethyl]-1,3-dioxan-4-yl}butyl pivalate

: 1372869-91-4
(3R)-3-hydroxy-4-{(4S,6R)-2-(4-methoxyphenyl)-6-[2-(pivaloyloxy)ethyl]-1,3-dioxan-4-yl}butyl pivalate

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol300832f

Reference yield:

: 1372869-97-0
1,7-bis(trimethylsilyl)-4-(tert-butyldimethylsilyloxy)hepta-1,6-diyne

: 1372870-09-1
(3R)-3-hydroxy-4-{(4R,6R)-2-(4-methoxyphenyl)-6-[2-(pivaloyloxy)ethyl]-1,3-dioxan-4-yl}butyl pivalate

: 1372869-91-4
(3R)-3-hydroxy-4-{(4S,6R)-2-(4-methoxyphenyl)-6-[2-(pivaloyloxy)ethyl]-1,3-dioxan-4-yl}butyl pivalate

Guidance literature:: Multi-step reaction with 9 steps

1.1: potassium carbonate / methanol / 3 h / 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

2.2: 3 h / -78 - 20 °C / Inert atmosphere

3.1: quinoline; 5% Pd/CaCO3 / 1-hexene / 0.08 h / Inert atmosphere

4.1: bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); triethylamine / 1,4-dioxane; water / 45 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 10 h / -78 - 0 °C / Inert atmosphere

6.1: pyridine; dmap / dichloromethane / 3 h / 0 °C / Inert atmosphere

7.1: peracetic acid; sodium acetate; potassium bromide / acetic acid / 15 h / 20 °C / Inert atmosphere

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

9.1: camphor-10-sulfonic acid / dichloromethane / 20 °C / Inert atmosphere

With pyridine; quinoline; peracetic acid; dmap; bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; n-butyllithium; camphor-10-sulfonic acid; 5% Pd/CaCO3; tetrabutyl ammonium fluoride; sodium acetate; diisobutylaluminium hydride; potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); triethylamine; potassium bromide; In tetrahydrofuran; 1,4-dioxane; methanol; 1-hexene; hexane; dichloromethane; water; acetic acid;
DOI:10.1021/ol300832f

Reference yield:

: 1372869-98-1
diethyl 5-(tert-butyldimethylsilyloxy)nona-2,7-diynedioate

: 1372870-09-1
(3R)-3-hydroxy-4-{(4R,6R)-2-(4-methoxyphenyl)-6-[2-(pivaloyloxy)ethyl]-1,3-dioxan-4-yl}butyl pivalate

: 1372869-91-4
(3R)-3-hydroxy-4-{(4S,6R)-2-(4-methoxyphenyl)-6-[2-(pivaloyloxy)ethyl]-1,3-dioxan-4-yl}butyl pivalate

Guidance literature:: Multi-step reaction with 7 steps

1: quinoline; 5% Pd/CaCO3 / 1-hexene / 0.08 h / Inert atmosphere

2: bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); triethylamine / 1,4-dioxane; water / 45 °C / Inert atmosphere

3: diisobutylaluminium hydride / tetrahydrofuran; hexane / 10 h / -78 - 0 °C / Inert atmosphere

4: pyridine; dmap / dichloromethane / 3 h / 0 °C / Inert atmosphere

5: peracetic acid; sodium acetate; potassium bromide / acetic acid / 15 h / 20 °C / Inert atmosphere

6: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

7: camphor-10-sulfonic acid / dichloromethane / 20 °C / Inert atmosphere

With pyridine; quinoline; peracetic acid; dmap; bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; camphor-10-sulfonic acid; 5% Pd/CaCO3; tetrabutyl ammonium fluoride; sodium acetate; diisobutylaluminium hydride; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); triethylamine; potassium bromide; In tetrahydrofuran; 1,4-dioxane; 1-hexene; hexane; dichloromethane; water; acetic acid;
DOI:10.1021/ol300832f