(S)-4-benzyl-3-((3R,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-4,6-dimethyloct-6-enoyl)oxazolidin-2-one

Base Information

Chemical Name:(S)-4-benzyl-3-((3R,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-4,6-dimethyloct-6-enoyl)oxazolidin-2-one
CAS No.:1610850-67-3
Molecular Formula:C₂₆H₄₁NO₅Si
Molecular Weight:475.701
Hs Code.:

Synonyms:(S)-4-benzyl-3-((3R,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-4,6-dimethyloct-6-enoyl)oxazolidin-2-one

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Chemical Property of (S)-4-benzyl-3-((3R,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-4,6-dimethyloct-6-enoyl)oxazolidin-2-one

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Technology Process of (S)-4-benzyl-3-((3R,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-4,6-dimethyloct-6-enoyl)oxazolidin-2-one

There total 5 articles about (S)-4-benzyl-3-((3R,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-4,6-dimethyloct-6-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:

: 132836-66-9
(S)-3-acetyl-4-benzyloxazolidin-2-one

: 760984-24-5
(2R,3R,4E)-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-4-hexenal

: 1610850-66-2
(S)-4-benzyl-3-((3S,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-4,6-dimethyloct-6-enoyl)oxazolidin-2-one

: 1610850-67-3
(S)-4-benzyl-3-((3R,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-4,6-dimethyloct-6-enoyl)oxazolidin-2-one

Guidance literature:: (S)-3-acetyl-4-benzyloxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.166667h;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 0 ℃; for 0.75h;

(2R,3R,4E)-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-4-hexenal; In dichloromethane; at -78 ℃; for 2h;
DOI:10.1016/j.tetlet.2014.04.079

Reference yield:

: 442159-37-7
(R)-4-benzyl-3-((2R,3R,E)-3-hydroxy-2,4-dimethylhex-4-enoyl)oxazolidin-2-one

: 1610850-66-2
(S)-4-benzyl-3-((3S,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-4,6-dimethyloct-6-enoyl)oxazolidin-2-one

: 1610850-67-3
(S)-4-benzyl-3-((3R,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-4,6-dimethyloct-6-enoyl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 - 20 °C

2.1: lithium borohydride / tetrahydrofuran; methanol / 1 h / 0 - 20 °C

3.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 1 h / 0 °C

4.1: di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.17 h / 0 °C

4.2: 0.75 h / -78 - 0 °C

4.3: 2 h / -78 °C

With 2,6-dimethylpyridine; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; sulfur trioxide pyridine complex; triethylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/j.tetlet.2014.04.079

Reference yield:

: 497-03-0
2-methylbut-2-enal

: 1610850-66-2
(S)-4-benzyl-3-((3S,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-4,6-dimethyloct-6-enoyl)oxazolidin-2-one

: 1610850-67-3
(S)-4-benzyl-3-((3R,4S,5R,E)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-4,6-dimethyloct-6-enoyl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: titanium tetrachloride / dichloromethane / 0.67 h / 0 °C

1.2: 4 h / 0 °C

2.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 - 20 °C

3.1: lithium borohydride / tetrahydrofuran; methanol / 1 h / 0 - 20 °C

4.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 1 h / 0 °C

5.1: di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.17 h / 0 °C

5.2: 0.75 h / -78 - 0 °C

5.3: 2 h / -78 °C

With 2,6-dimethylpyridine; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; sulfur trioxide pyridine complex; titanium tetrachloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/j.tetlet.2014.04.079