(R)-4-benzyl-3-((2R,3R,6S,7R,E)-7-(((tert-butyl)dimethylsilyl)oxy)-2,4,6-trimethyl-3-((trimethylsilyl)oxy)oct-4-enoyl)oxazolidin-2-one

Base Information

Chemical Name:(R)-4-benzyl-3-((2R,3R,6S,7R,E)-7-(((tert-butyl)dimethylsilyl)oxy)-2,4,6-trimethyl-3-((trimethylsilyl)oxy)oct-4-enoyl)oxazolidin-2-one
CAS No.:1440545-59-4
Molecular Formula:C₃₀H₅₁NO₅Si₂
Molecular Weight:561.91
Hs Code.:

Synonyms:(R)-4-benzyl-3-((2R,3R,6S,7R,E)-7-(((tert-butyl)dimethylsilyl)oxy)-2,4,6-trimethyl-3-((trimethylsilyl)oxy)oct-4-enoyl)oxazolidin-2-one

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Chemical Property of (R)-4-benzyl-3-((2R,3R,6S,7R,E)-7-(((tert-butyl)dimethylsilyl)oxy)-2,4,6-trimethyl-3-((trimethylsilyl)oxy)oct-4-enoyl)oxazolidin-2-one

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Technology Process of (R)-4-benzyl-3-((2R,3R,6S,7R,E)-7-(((tert-butyl)dimethylsilyl)oxy)-2,4,6-trimethyl-3-((trimethylsilyl)oxy)oct-4-enoyl)oxazolidin-2-one

There total 7 articles about (R)-4-benzyl-3-((2R,3R,6S,7R,E)-7-(((tert-butyl)dimethylsilyl)oxy)-2,4,6-trimethyl-3-((trimethylsilyl)oxy)oct-4-enoyl)oxazolidin-2-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:

: 75-77-4
chloro-trimethyl-silane

: 1440545-72-1
(R)-4-benzyl-3-((2R,3R,6S,7R,E)-7-(((tert-butyl)dimethylsilyl)oxy)-3-hydroxy-2,4,6-trimethyloct-4-enoyl)oxazolidin-2-one

: 1440545-59-4
(R)-4-benzyl-3-((2R,3R,6S,7R,E)-7-(((tert-butyl)dimethylsilyl)oxy)-2,4,6-trimethyl-3-((trimethylsilyl)oxy)oct-4-enoyl)oxazolidin-2-one

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ol401186f

Reference yield:

: 1044263-52-6
(4S,4'S,5'R,2'E)-3-[5'-hydroxy-2',4'-dimethyl-2'-hexenoyl]-4-isopropyl-1,3-oxazolidin-2-one

: 1440545-59-4
(R)-4-benzyl-3-((2R,3R,6S,7R,E)-7-(((tert-butyl)dimethylsilyl)oxy)-2,4,6-trimethyl-3-((trimethylsilyl)oxy)oct-4-enoyl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1H-imidazole; dmap / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

1.2: 19 h / 0 - 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate / tetrahydrofuran / 12.5 h / 0 - 20 °C / Inert atmosphere

3.1: triethylamine; dimethyl sulfoxide; sulfur trioxide pyridine complex / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

4.1: triethylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 1 h / -10 °C / Inert atmosphere

4.2: 3 h / -78 - 0 °C / Inert atmosphere

5.1: 1H-imidazole / dichloromethane / 2 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; sodium tetrahydroborate; di-n-butylboryl trifluoromethanesulfonate; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 3.1: |Parikh-Doering Oxidation / 4.1: |Evans Aldol Reaction / 4.2: |Evans Aldol Reaction;
DOI:10.1021/ol401186f

Reference yield:

: 1440545-70-9
(S)-3-((4S,5R,E)-5-(((tert-butyl)dimethylsilyl)oxy)-2,4-dimethylhex-2-enoyl)-4-isopropyloxazolidin-2-one

: 1440545-59-4
(R)-4-benzyl-3-((2R,3R,6S,7R,E)-7-(((tert-butyl)dimethylsilyl)oxy)-2,4,6-trimethyl-3-((trimethylsilyl)oxy)oct-4-enoyl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium tetrahydroborate / tetrahydrofuran / 12.5 h / 0 - 20 °C / Inert atmosphere

2.1: triethylamine; dimethyl sulfoxide; sulfur trioxide pyridine complex / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

3.1: triethylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 1 h / -10 °C / Inert atmosphere

3.2: 3 h / -78 - 0 °C / Inert atmosphere

4.1: 1H-imidazole / dichloromethane / 2 h / 20 °C / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; di-n-butylboryl trifluoromethanesulfonate; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 2.1: |Parikh-Doering Oxidation / 3.1: |Evans Aldol Reaction / 3.2: |Evans Aldol Reaction;
DOI:10.1021/ol401186f