(4S,E)-1-((4S,5S)-5-(benzyloxy)-2-phenyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)pent-1-en-3-one

Base Information

Chemical Name:(4S,E)-1-((4S,5S)-5-(benzyloxy)-2-phenyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)pent-1-en-3-one
CAS No.:1393661-52-3
Molecular Formula:C₂₈H₃₈O₅Si
Molecular Weight:482.692
Hs Code.:

Synonyms:(4S,E)-1-((4S,5S)-5-(benzyloxy)-2-phenyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)pent-1-en-3-one

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Chemical Property of (4S,E)-1-((4S,5S)-5-(benzyloxy)-2-phenyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)pent-1-en-3-one

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Technology Process of (4S,E)-1-((4S,5S)-5-(benzyloxy)-2-phenyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)pent-1-en-3-one

There total 2 articles about (4S,E)-1-((4S,5S)-5-(benzyloxy)-2-phenyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)pent-1-en-3-one 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:

: (4R,5S)-5-(benzyloxy)-2-phenyl-1,3-dioxane-4-carbaldehyde

: 131569-94-3
dimethyl [(S)-3-(tert-butyldimethylsilyloxy)butan-2-on-1-yl]phosphonate

: 1393661-52-3
(4S,E)-1-((4S,5S)-5-(benzyloxy)-2-phenyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)pent-1-en-3-one

Guidance literature:: dimethyl [(S)-3-(tert-butyldimethylsilyloxy)butan-2-on-1-yl]phosphonate; With caesium carbonate; In acetonitrile; at 20 ℃; for 0.75h; Inert atmosphere;

(4R,5S)-5-(benzyloxy)-2-phenyl-1,3-dioxane-4-carbaldehyde; In tetrahydrofuran; at -15 ℃; for 0.5h; stereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2012.06.002

Reference yield:

: 107938-31-8
(2S,3S)-1,3-O-Benzylidene-2-O-benzylthreitol

: 1393661-52-3
(4S,E)-1-((4S,5S)-5-(benzyloxy)-2-phenyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)pent-1-en-3-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / Reflux; Inert atmosphere

2.1: caesium carbonate / acetonitrile / 0.75 h / 20 °C / Inert atmosphere

2.2: 0.5 h / -15 °C / Inert atmosphere

With caesium carbonate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In ethyl acetate; acetonitrile; 2.2: Wittig reaction;
DOI:10.1016/j.tet.2012.06.002

Reference yield: 92.0%

: 1393661-52-3
(4S,E)-1-((4S,5S)-5-(benzyloxy)-2-phenyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)pent-1-en-3-one

: 1393661-53-4
(3S,4S,E)-1-((4S,5S)-5-(benzyloxy)-2-phenyl-1,3-dioxan-4-yl)-4-((tert-butyldimethylsilyl)oxy)pent-1-en-3-ol

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride heptahydrate; In methanol; at -78 ℃; for 1.16667h; Inert atmosphere;
DOI:10.1016/j.tet.2012.06.002