(2S,4R,5R)-1-((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-methoxy-7-((4-methoxybenzyl)oxy)-2,4-dimethylheptane-1,3-dione

Base Information

Chemical Name:(2S,4R,5R)-1-((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-methoxy-7-((4-methoxybenzyl)oxy)-2,4-dimethylheptane-1,3-dione
CAS No.:1551543-85-1
Molecular Formula:C₂₈H₃₅NO₇
Molecular Weight:497.588
Hs Code.:

Synonyms:(2S,4R,5R)-1-((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-methoxy-7-((4-methoxybenzyl)oxy)-2,4-dimethylheptane-1,3-dione

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Chemical Property of (2S,4R,5R)-1-((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-methoxy-7-((4-methoxybenzyl)oxy)-2,4-dimethylheptane-1,3-dione

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Technology Process of (2S,4R,5R)-1-((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-methoxy-7-((4-methoxybenzyl)oxy)-2,4-dimethylheptane-1,3-dione

There total 1 articles about (2S,4R,5R)-1-((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-methoxy-7-((4-methoxybenzyl)oxy)-2,4-dimethylheptane-1,3-dione 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: 73.0%

: 1551543-57-7
(2S,4R,5R)-1-((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-hydroxy-7-((4-methoxybenzyl)oxy)-2,4-dimethylheptane-1,3-dione

: 420-37-1
trimethoxonium tetrafluoroborate

: 1551543-85-1
(2S,4R,5R)-1-((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-methoxy-7-((4-methoxybenzyl)oxy)-2,4-dimethylheptane-1,3-dione

Guidance literature:: With proton sponge; In dichloromethane; at 20 ℃;
DOI:10.1021/ol500004k

Reference yield:

: 1551543-85-1
(2S,4R,5R)-1-((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-methoxy-7-((4-methoxybenzyl)oxy)-2,4-dimethylheptane-1,3-dione

: 1551543-88-4
(2R,3S,4S,5R)-5-methoxy-7-((4-methoxybenzyl)oxy)-2,4-dimethylheptane-1,3-diol

: C₁₈H₃₀O₅

Guidance literature:: With lithium borohydride; In diethyl ether; at -26 - -15 ℃; for 0.333333h; Overall yield = 88 %; Overall yield = 0.207 g;
DOI:10.1021/ol500004k

Reference yield:

: 1551543-85-1
(2S,4R,5R)-1-((S)-4-benzyl-2-oxooxazolidin-3-yl)-5-methoxy-7-((4-methoxybenzyl)oxy)-2,4-dimethylheptane-1,3-dione

: 1551543-75-9
(3aR,6S,7S,8E,11R,12E,13aR)-6-((4R,5S,6R,7R,E)-5-((tert-butyldimethylsilyl)oxy)-7-methoxy-9-((4-methoxybenzyl)oxy)-4,6-dimethylnon-2-en-2-yl)-2,2,7,11-tetramethyl-6,7,10,11-tetrahydro-3aH-[1,3]dioxolo[4,5-c ][1]oxacyclododecin-4(13aH)-one

Guidance literature:: Multi-step reaction with 9 steps

1: lithium borohydride / diethyl ether / 0.33 h / -26 - -15 °C

2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 7 h / 20 °C

3: dichloromethane / 18 h / 20 °C

4: 2,6-dimethylpyridine / dichloromethane / 3 h / 0 °C

5: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 °C

6: Dess-Martin periodane / dichloromethane / 0 °C

7: (R,R)-trans-EZ-crotyl mix / dichloromethane / 40 h / 20 °C

8: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 14 h / 20 °C / Inert atmosphere

9: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 17 h

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; lithium borohydride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; (R,R)-trans-EZ-crotyl mix; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; diethyl ether; dichloromethane; 3: |Wittig Olefination;
DOI:10.1021/ol500004k