(E)-ethyl 3-(((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-(2-oxoethyl)tetrahydro-2H-pyran-3-yl)oxy)acrylate

Base Information

Chemical Name:(E)-ethyl 3-(((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-(2-oxoethyl)tetrahydro-2H-pyran-3-yl)oxy)acrylate
CAS No.:1338566-11-2
Molecular Formula:C₂₇H₃₂O₇
Molecular Weight:468.547
Hs Code.:

Synonyms:(E)-ethyl 3-(((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-(2-oxoethyl)tetrahydro-2H-pyran-3-yl)oxy)acrylate

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Chemical Property of (E)-ethyl 3-(((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-(2-oxoethyl)tetrahydro-2H-pyran-3-yl)oxy)acrylate

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Technology Process of (E)-ethyl 3-(((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-(2-oxoethyl)tetrahydro-2H-pyran-3-yl)oxy)acrylate

There total 6 articles about (E)-ethyl 3-(((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-(2-oxoethyl)tetrahydro-2H-pyran-3-yl)oxy)acrylate 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: 95.0%

: 1338566-10-1
(E)-ethyl 3-(((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-((1,3-dithian-2-yl)methyl)tetrahydro-2H-pyran-3-yl)oxy)acrylate

: 1338566-11-2
(E)-ethyl 3-(((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-(2-oxoethyl)tetrahydro-2H-pyran-3-yl)oxy)acrylate

Guidance literature:: With sodium hydrogencarbonate; methyl iodide; In water; acetonitrile; at 20 ℃; for 22h;
DOI:10.1021/ol202467z

Reference yield:

: 1338566-06-5
((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)methyl trifluoromethanesulfonate

: 1338566-11-2
(E)-ethyl 3-(((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-(2-oxoethyl)tetrahydro-2H-pyran-3-yl)oxy)acrylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -20 °C / Inert atmosphere

1.2: 1 h / -20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C

3.1: 4-methyl-morpholine / dichloromethane / 2 h / 20 °C

4.1: sodium hydrogencarbonate; methyl iodide / water; acetonitrile / 22 h / 20 °C

With 4-methyl-morpholine; n-butyllithium; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; methyl iodide; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile;
DOI:10.1021/ol202467z

Reference yield:

: 1338566-07-6
(((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-((1,3-dithian-2-yl)methyl)tetrahydro-2H-pyran-3-yl)oxy)-t-butyldimethylsilane

: 1338566-11-2
(E)-ethyl 3-(((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-(2-oxoethyl)tetrahydro-2H-pyran-3-yl)oxy)acrylate

Guidance literature:: Multi-step reaction with 3 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C

2: 4-methyl-morpholine / dichloromethane / 2 h / 20 °C

3: sodium hydrogencarbonate; methyl iodide / water; acetonitrile / 22 h / 20 °C

With 4-methyl-morpholine; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; methyl iodide; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1021/ol202467z