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

Base Information

• Chemical Name: (S)-4-benzyl-3-((2S,3R,4S,5R)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethyloct-6-ynoyl)oxazolidin-2-one
• CAS No.: 1439376-73-4
• Molecular Formula: C₂₆H₃₉NO₅Si
• Molecular Weight: 473.685

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

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

Chemical Property:

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

There total 5 articles about (S)-4-benzyl-3-((2S,3R,4S,5R)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethyloct-6-ynoyl)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: 89.0%

(S)-4-benzyl-3-((2S,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloct-6-ynoyl)oxazolidin-2-one (1439376-72-3) + t-butyldimethylsiyl triflate (69739-34-0) → (S)-4-benzyl-3-((2S,3R,4S,5R)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethyloct-6-ynoyl)oxazolidin-2-one (1439376-73-4)

Guidance literature:

With triethylamine; In dichloromethane; at -78 ℃; for 3h; regioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201206670

Reference yield:

(S)-4-benzyl-3-propionyl-2-oxazolidinone (131685-53-5,101711-78-8) → (S)-4-benzyl-3-((2S,3R,4S,5R)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethyloct-6-ynoyl)oxazolidin-2-one (1439376-73-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0 - 2 °C / Inert atmosphere

1.2: 0.5 h / -78 °C / Inert atmosphere

2.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 3 h / -15 °C / Inert atmosphere

3.1: triethylamine; tin(II) trifluoromethanesulfonate / dichloromethane / 1 h / -30 °C / Inert atmosphere

3.2: 0.75 h / -78 °C / Inert atmosphere

4.1: tetramethylammonium triacetoxyborohydride / acetonitrile; acetic acid / -50 - 10 °C / Inert atmosphere

5.1: triethylamine / dichloromethane / 3 h / -78 °C / Inert atmosphere

With tin(II) trifluoromethanesulfonate; di-n-butylboryl trifluoromethanesulfonate; sulfur trioxide pyridine complex; triethylamine; tetramethylammonium triacetoxyborohydride; In dichloromethane; acetic acid; dimethyl sulfoxide; acetonitrile; 1.2: |Aldol Addition / 3.2: |Aldol Addition;

DOI:10.1002/anie.201206670

Reference yield:

(4S,2'S,3'R)-3-(2'-methyl-3'-hydroxypentanoyl)-4-benzyl-2-oxazolidinone (124356-91-8) → (S)-4-benzyl-3-((2S,3R,4S,5R)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethyloct-6-ynoyl)oxazolidin-2-one (1439376-73-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 3 h / -15 °C / Inert atmosphere

2.1: triethylamine; tin(II) trifluoromethanesulfonate / dichloromethane / 1 h / -30 °C / Inert atmosphere

2.2: 0.75 h / -78 °C / Inert atmosphere

3.1: tetramethylammonium triacetoxyborohydride / acetonitrile; acetic acid / -50 - 10 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 3 h / -78 °C / Inert atmosphere

With tin(II) trifluoromethanesulfonate; sulfur trioxide pyridine complex; triethylamine; tetramethylammonium triacetoxyborohydride; In dichloromethane; acetic acid; dimethyl sulfoxide; acetonitrile; 2.2: |Aldol Addition;

DOI:10.1002/anie.201206670

upstream raw materials:

(4S,2'S,3'R)-3-(2'-methyl-3'-hydroxypentanoyl)-4-benzyl-2-oxazolidinone

(S)-1-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-2-methylpentane-1,3-dione

(2S,4R,5R)-1-((S)-4-benzyl-2-oxo-oxazolidin-3-yl)-5-hydroxy-2,4-dimethyloct-6-yne-1,3-dione

(S)-4-benzyl-3-((2S,3R,4S,5R)-3,5-dihydroxy-2,4-dimethyloct-6-ynoyl)oxazolidin-2-one

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