(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

Base Information

Chemical Name:(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
CAS No.:1338566-10-1
Molecular Formula:C₃₀H₃₈O₆S₂
Molecular Weight:558.76
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 4 articles about (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 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: 99.0%

: 1338566-08-7
(2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-((1,3-dithian-2-yl)methyl)tetrahydro-2H-pyran-3-ol

: 623-47-2
propynoic acid ethyl ester

: 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

Guidance literature:: With 4-methyl-morpholine; In dichloromethane; at 20 ℃; for 2h;
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

: 1338566-10-1
(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

Guidance literature:: Multi-step reaction with 3 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

With 4-methyl-morpholine; n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; dichloromethane;
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

: 1338566-10-1
(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

Guidance literature:: Multi-step reaction with 2 steps

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

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

With 4-methyl-morpholine; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol202467z